North Side, Cayman Islands Vacation Rentals

Explore 280 vacation rentals, homes, and villas in North Side for your next getaway or business trip. Experience the privacy of a home with premium amenities such as Air Condition Homes, Homes with Pools and Homes with Free Parking, designed for a more comfortable and convenient stay. Every home is curated and professionally managed, with 24/7 local support, high-speed Wi-Fi, and premium linens included. With homes starting as low as $120 per night and featuring up to 12 bedrooms and 14 bathrooms, there's an option for every trip, from family vacations and group getaways to extended stays. However you're looking to experience your stay, Homes & Villas by Marriott has your next vacation home waiting. Marriott Bonvoy members can also earn and redeem points on every booking.

280 Vacation Rentals in North Side

Maravilla

North Side, KY
4 Bedrooms • 9 Guests

Oct 14 - 19
$489 night

***PROPERTY DESCRIPTION*** Welcome to Maravilla, a bright and inviting 4-bedroom, two-story oceanfront villa located on the tranquil North Side. With direct beach access and spacious interiors, Maravilla is designed for families and groups seeking a peaceful coastal getaway. Outside, the villa’s oceanfront setting delivers stunning panoramic ocean views and refreshing sea breezes. Step down to the beach for sunbathing, reef-protected snorkeling, or quiet morning walks along the shoreline. Mature trees provide shade along the beach. Guests can also take refuge from the island sun under the elevated pergola with sun loungers overlooking the ocean. Step inside to an airy, open-concept layout filled with natural light and dazzling ocean views. Soft neutrals, modern lighting, and tasteful décor create a warm and comfortable atmosphere throughout the home. The main living area features an oversized sectional sofa and a large HD cable television—perfect for movie nights after a day in the sand. For added entertainment, there’s a convertible pool & ping-pong table, giving guests the perfect spot to unwind and enjoy friendly competition. The villa’s expansive foyer and great room offer soaring ceilings, elegant columns, and polished travertine flooring that enhances the modern ambiance. A sleek staircase leads to the upper level, where you’ll find additional living spaces and bedrooms, giving your group plenty of room to spread out. ***Sleeping Arrangements*** (Sleeps 9 guests total, 8 adults max) -- Bedroom 1: upper-level, king bed, ocean views, private sunroom, shares adjacent bathroom with double vanity, and shower bath. -- Bedroom 2: upper-level, king bed, ocean views, private sunroom, shares adjacent bathroom with double vanity, and shower bath. -- Bedroom 3: upper-level, queen bed, shares hall bathroom with shower. -- Bedroom 4: upper-level, twin beds, shares hall bathroom with shower. -- Additional bedding: lower-level daybed suitable for one child. -- Additional bath: lower-level full bath with shower. Maravilla’s fully equipped kitchen features crisp white cabinetry, granite countertops, an oven, microwave, and ample workspace—ideal for preparing anything from quick breakfasts to island-inspired dinners. Whether you choose to cook or hire a private chef, this kitchen is built for convenience and style. For nights out on the town, you’re only a short drive away from food + drinks at the Rum Point Club and Kaibo. A small grocery store, Chisholm’s, is also just a short walk away. Whether you’re seeking serenity, family time, or a picture-perfect Caribbean retreat, Maravilla offers the ideal setting to create unforgettable island memories. Note: Cruiser bicycles and kayaks are available at discounted rental rates with free delivery. A signed waiver is required. ***NEARBY ATTRACTIONS*** -- Short walk to the nearest grocery, Chisholm’s Grocery. -- 5-minute drive east to Over the Edge restaurant and Cayman Crystal Caves -- 4 miles from our Property Manager Welcome Center -- 5 miles west to the Rum Point Club and Bioluminescent Bay -- 6 miles to the Kaibo Beach Bar & Grill & Starfish Point -- 8 miles to the nearest supermarket, Foster’s Express -- 10 miles to Tukka East Restaurant & Bar and the Cayman Parrot Sanctuary -- 11 miles to La Casita Taco & Tequilla Bar -- 21 miles (40-minute drive) from Owen Roberts Airport (GCM) ***GETTING AROUND*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget, Marshalls, or Hertz. ***RATE DETAILS*** -- 13% Occupancy tax added to rates. -- 10% Guest Service Fee added to rates. -- Accidental Damage Protection added to rates. -- A Departure Cleaning Fee is required for all stays. ***BOOKING RULES*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays are welcome but subject to a higher cleaning fee. Please inquire to book. -- Must be 25 years or older to book and must occupy the property during the entire stay. ***GCVC GUEST SERVICES*** The following perks are provided during your stay! Member Benefits -- Free snorkel gear for all members of your group -- Free pack-n-plays, booster seats, & baby gates -- Free Bluetooth speakers, beach coolers, Apple TVs, and more convenience items to enhance your stay. -- 10% Advance Booking Discount towards a private charter to Stingray City -- On-island Welcome Center with guest-only private gym (18+ yrs.) and business hub (computers, printer, scanner, & FedEx/DHL supplies) -- Guest Benefit card for 10% discounts at select restaurants and businesses -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors, guest services desk assistance At-Villa Benefits -- Complimentary early check-in, if no check out on the same day -- Day-after-arrival guest services follow-up -- Hotel-grade bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- Tandem/Single kayaks available for discounted rental; signed waiver required. *** BEACH NOTES *** All beaches in Grand Cayman are technically public, since the Crown extends to the high-water mark. Be advised that the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. *** OCEAN DEBRIS & SARGASSUM SEAWEED *** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. We try our best to work around Mother Nature.

Beautiful 3 Bd Beachfront Home North Side Sleeps 7

North Side, Grand Cayman, KY
3 Bedrooms • 7 Guests

Oct 8 - 11
$206 night

Welcome to Azure Breeze #6, a recently renovated beachfront property. This stunning 3-bedroom, 2-bathroom home, nestled within a small 6-unit complex, invites you to embark on an unforgettable vacation in the Cayman Islands. Located on the northern coast of Grand Cayman, Azure Breeze offers convenient proximity to Crystal Caves, Rum Point, and Cayman Kai, ensuring access to a variety of exciting adventures. With comfortable accommodations for up to 7 guests, including a king, queen, and a full bed with an overhead single bunk, this spacious two-story retreat is thoughtfully designed for both relaxation and family fun. Step outside onto the secluded beach and sway in a hammock beneath the coconut trees, as gentle sea breezes embrace you. Watch as children joyfully play on the shore or venture into the crystal-clear waters for snorkeling and kayaking adventures. Inside, every detail of this exquisite villa exudes elegance. Revel in breathtaking views from multiple windows, capturing the essence of the coastal paradise. Upstairs, sliding doors invite refreshing breezes and illuminate the main living room, which offers a tranquil space to unwind. The patio on the main floor is perfect for entertainment and relaxation, and features a beachside BBQ area with a provided propane grill. On the ground floor, a cozy bedroom with a queen-sized bed and a bathroom with a shower await. The recently renovated kitchen showcases modern appliances and utensils, ensuring a seamless culinary experience. While Azure Breeze #6 provides a private sanctuary, it remains conveniently close to a local grocery store, attractions, and restaurants, ensuring your needs and desires are effortlessly fulfilled. Indulge in the allure of this coastal oasis, where the pristine beach, stylish accommodations, and proximity to local treasures converge to create an unforgettable vacation experience. To fully embrace the serene ambiance of North Side, we suggest renting a car for convenient transportation, as public options may be limited. With George Town approximately 50 minutes away, having a car will grant you the freedom to explore the area’s hidden treasures and embrace the picturesque beauty at your own leisurely pace. A 2-seater kayak with lifejackets and snorkeling gears are available at the property. Please note that the A/C system in this rental is designed with a lower limit of 74°F and includes door sensors that turn off the A/C when doors are left open. Please ensure that the doors in the condo are closed at all times except when entering or exiting. These features are in place to ensure the system operates efficiently and to prevent issues such as mold, which can occur in humid environments near to the ocean. We appreciate your understanding and cooperation in adhering to these settings to maintain a comfortable and healthy environment during your stay. If the booking website does not collect it directly, a refundable security deposit of US$750.00 will be collected by the property prior to your stay. We reserve the right to substitute equal or better accommodation in the event of a double booking or if the rental is unavailable for any reason, including but not limited to sale or repair.

Coastal Charm

North Side, KY
3 Bedrooms • 9 Guests

Oct 8 - 13
$604 night

***Property Description*** Welcome to Coastal Charm, a newly constructed 3-bedroom home nestled along Grand Cayman’s tranquil North Side. Thoughtfully designed with modern coastal elegance, this inviting retreat offers the perfect blend of comfort, style, and island serenity—ideal for families or small groups seeking a relaxing Caribbean escape. Step inside to an airy open-concept living space where floor-to-ceiling glass doors frame sweeping ocean views, filling the home with natural light. The seamless flow between the living area, dining area, and gourmet kitchen creates a welcoming gathering space. The kitchen features high-end appliances, a spacious island with seating, and everything needed to prepare meals with ease—whether you’re enjoying a casual breakfast indoors or an island cookout at sunset. The living area is designed for both comfort and style, with plush seating, warm natural textures, and calming neutral tones that reflect the beauty of the surrounding coastline. The home is equipped with central air conditioning, fiber optic wifi, and cable SmartTVs to keep you cool and connected during your stay. Just beyond, the tropical outdoors invites you to unwind, with a private pool, lounge seating, and reef-protected snorkeling in the crystal-clear Caribbean waters—perfect for swimming, kayaking, or simply soaking in the view. Coastal Charm offers three well-appointed bedroom suites designed for cloud-nine comfort. Each room provides a peaceful retreat after a day in the sun, with quality furnishings and a soothing coastal aesthetic. **Sleeping Arrangements** (Sleeps 9 guests, 6 adults max) -- Bedroom 1: lower level, ocean view, king bed, HD TV, walk-out access to pool deck, ensuite with double vanity and shower. -- Bedroom 2: upper level, ocean view, king bed, HD TV, ensuite with shower. -- Bedroom 3: upper level, ocean view, twin over queen bunk bed, HD TV, ensuite with shower. -- Additional Bedding: sleeper sofa in upper den, suitable for 2 children only. Located in the peaceful North Side, Coastal Charm offers a more secluded island experience while still being within easy driving distance of local attractions, dining, and adventure. Spend your days at the Rum Point Club snorkeling along the pier, dining with your toes in the sand, or staying in for a relaxing day in your oceanfront oasis. Whether you’re seeking quiet mornings by the water, memorable family antics, or a stylish island getaway, Coastal Charm delivers a refined yet laid-back Caribbean experience you won’t forget. *Notes: 1) Housekeeping can be added after booking; 2) Cruiser bikes for adults and kids, plus kayaks, are available for discounted rental. A signed waiver is required. =================== ***NEARBY ATTRACTIONS*** -- 2-minute drive east to the nearest grocery, Chisholm’s Grocery. -- 6-minute drive east to Over the Edge restaurant and Cayman Crystal Caves -- 7-minute drive west to Rum Point Beach and Bioluminescent Bay -- 9-minute drive west to the Kaibo Beach Bar & Grill & Starfish Point -- 10-minute drive from our Welcome Center -- 15-minute drive to the nearest supermarket, Foster’s Express -- 19-minute drive to Tukka East Restaurant & Bar and the Cayman Parrot Sanctuary -- 21-minute drive to La Casita Taco & Tequilla Bar -- 45-minute drive from Owen Roberts Airport (GCM) ***GETTING AROUND*** The entire island is only 22 miles wide, so you are never too far from anywhere on Grand Cayman. However, a rental car is highly recommended. Taxis are unreliable and expensive beyond Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Avis, or Marshalls. We’ll provide a 20% promo code for any rentals at Budget Cayman after booking. You can also rent kids’ or adult bikes to cruise the shoreline. Helmets and locks provided. ***RATE DETAILS*** -- 13% Occupancy Tax added to rates. -- 10% Guest Service Fee added to rates. -- Accidental Damage Protection added to rates. -- A Departure Cleaning Fee is required for all stays. ***BOOKING RULES*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays are welcome but subject to a higher cleaning fee. Please inquire to book. -- Must be 25 years or older to book and must occupy the property during the entire stay. ***VILLA CLEANING*** All villas are cleaned and sanitized before each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling will be coordinated with your property manager on arrival. ***BEACH NOTES*** All beaches in Grand Cayman are technically public since the Crown owns up to the high-water mark. The shoreline quality behind your property may vary slightly from the images on our website due to shifting tides and weather patterns. The beach next door is also always available for your use. The homes on the oceanfront in Rum Point offer great reef-protected snorkeling. The beaches usually have plenty of white sand, but can also have spots of rocky “ironshore”. We recommend wearing pool shoes or fins for foot protection. The big draw to this area is the Rum Point Club, a public beachfront destination with beach service, food + drinks, a gift shop, excursions, and snorkeling. Also nearby is the Kaibo, another seaside dining spot with a cafe, beach bar & grill, and a fine dining restaurant. ***OCEAN DEBRIS & SARGASSUM*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival-- we try our best to work around Mother Nature.

Timeless Paradise

Rum Point, KY
11 Bedrooms • 28 Guests

Nov 12 - 17
$4,019 night

*** PROPERTY OVERVIEW *** Discover unparalleled Caribbean grandeur and indulge in luxurious island living at this exclusive vacation villa, nestled in the prestigious Rum Point neighborhood. This beachfront paradise is more than just a home; it’s an experience you won’t soon forget. Welcome to Timeless Paradise. This newly constructed, 3-story ocean estate stands 18 feet above sea level and spans an astounding 15,000 square feet. All 11 bedrooms and 13 bathrooms were meticulously designed with lavish fixtures and designer furnishings. Upon entering through the grand entryway, you’ll be greeted with elevated panoramic ocean views that will leave you breathless. The villa’s open floor plan, punctuated with eleven-foot ceilings and a stunning blue granite accent wall, offers seamless flow from the kitchen, dining, and living areas. The villa’s 11-bedroom suites are spread across 3 stories with 2 on the main level, 6 on the upper level, and 3 on the lower level. **Sleeping Arrangements** (Licensed to sleep 24 adults, 28 guests max.) -- Bedroom #1: main level, primary suite, ocean views, king platform bed, television + soundbar, walkout access to the veranda lounge and pool deck, ensuite with dual vanity, deep soaking tub, and glass shower with water wand plus rainfall shower head. -- Bedroom #2: main level, island views, four full-sized beds, ensuite with shower. -- Bedroom #3: upper level, ocean views, king bed, television, walkout access to the west veranda balcony, ensuite with dual vanity and walk-in shower. -- Bedroom #4: upper level, ocean views, king bed, television, walkout access to a shared balcony, ensuite with dual vanity and walk-in shower. -- Bedroom #5: upper level, ocean views, king bed, television, walkout access to a shared balcony, ensuite with dual vanity and walk-in shower. -- Bedroom #6: upper level, ocean views, king bed, television, walkout access to the east veranda balcony, ensuite with dual vanity and walk-in shower. -- Bedroom #7: upper level, island views, king bed, television, ensuite with walk-in shower. -- Bedroom #8: upper level, island views, king bed, television, ensuite with walk-in shower. -- Bedroom #9: lower level, king bed, television, ensuite with walk-in shower. -- Bedroom #10: lower level, king bed + queen daybed, television, ensuite with walk-in shower. -- Bedroom #11: lower level, king bed, television, shares downstairs full bathroom equipped with a walk-in shower. For resort-like features, this villa has it all. Bask along the freshwater pool and sun deck complete with plush loungers, day beds, and comfy lounge seating. The lower level features a 17-seat projection cinema with leather recliners, perfect for movie nights or big sporting events. The lower-level game room is sure to wow younger guests, complete with tabletop games (billiards, ping pong, and air hockey) and a video arcade. A fully-equipped gym with a sauna is also available for vacationing fitness enthusiasts. A 7-zone air conditioning system and high-speed wifi will keep everyone cool and connected throughout their stay. A state-of-the-art kitchen comes equipped with top-of-the-line Thor appliances, quartz countertops, and a full butler’s pantry. A second full kitchen is located on the lower level, complete with appliances, island seating, and a dining table for 10 guests. The outdoor kitchen pavilion along the pool deck will delight grill masters with a suite of appliances and a propane grill. Elevate your stay and hire a private gourmet chef for a night of fine dining or poolside brunch service. The formal dining area seats 14 guests, and the veranda dining tables seat 12. This unmatched beachfront estate is the epitome of luxury, comfort, and smart home technology, offering you an unforgettable vacation experience. *Note: Bike rentals and single/tandem kayaks are available for discounted rental. A signed waiver is required. ==================== *** RATE DETAILS *** -- 13% Occupancy Tax added to all rates. -- 12.90% Service Fee is added to all rates. -- A Departure Cleaning Fee is added to all rates. *** BOOKING RULES *** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays are welcome but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 years or older to book and must occupy the property during the entire stay. -- Check in is 4:00 pm; Check out is 10:00 am ***GCVC GUEST SERVICES*** The 12.90% Service Fee includes your Guest Services Membership. Member Benefits -- Platinum Concierge services - upon confirmation, before arrival, and during your stay. -- Centralized on-island Guest Services and Welcome Center. -- Complimentary use of snorkel equipment. -- 10% Advance Booking Discount towards a private charter. -- Guest benefit card for 10% discount at restaurants and local vendors. -- Unlimited use of our private Fitness Center (must be 18 or over). -- Business Center Access: computers, printer, scanner, & Fedex/DHL supplies. -- Airport fast-track VIP arrival (fee charged by CAA) -- Arrange airport pick-up & rental vehicles (fee applies) -- Guest parcel receipt & hold at check-in -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Special event/dinner reservations At-Villa Benefits -- Welcome amenity basket with local products. -- Pre-stocking of groceries & beverages (delivery fee applies). -- Complimentary early check-in, if no check-out on the same day. -- Complimentary (delivered) pack-n-plays, booster seats, & baby gates. -- Day-after-arrival & mid-week guest services follow-up. -- Complimentary use of Apple TVs, Bluetooth speakers, beverage coolers, and more. -- Gilchrist & Soames bath products. -- Complimentary memory foam roll-away bed delivery. -- Arrange private chefs, family-style cooks, babysitting, or group photography. -- $5,000 of Accidental Villa Damage Protection. -- Tandem kayaks available for discounted rental; signed waiver required. ***NEARBY ATTRACTIONS*** -- 3-minute drive to the nearest grocery store, Chisholm’s Grocery. -- 7-minute drive east to Over the Edge restaurant and Cayman Crystal Caves -- 6.2 miles from our Guest Services & Welcome Center -- 2.6 miles west to the Rum Point Club and Bioluminescent Bay -- 3.6 miles to the Kaibo Beach Bar & Grill & Starfish Point -- 10 miles east to the nearest supermarket, Foster’s Express, and the resorts at Morritts and Wyndham Reef Resort. -- 12.1 miles to Tukka East Restaurant & Bar and the Cayman Parrot Sanctuary -- 13 miles to La Casita Taco & Tequilla Bar -- 24 miles (45-minute drive) from Owen Roberts Airport (GCM) ***GETTING AROUND*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget, Marshalls, or Hertz. *** BEACH NOTES *** All beaches in Grand Cayman are technically public, since the Crown extends to the high-water mark. Be advised that the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. *** OCEAN DEBRIS & SARGASSUM SEAWEED *** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. We try our best to work around Mother Nature.

The Mastic Cana Cottage | 2BR w/ Private Pool on 11 Acre North Side Estate

North Side, Grand Cayman, KY
2 Bedrooms • 6 Guests

Oct 31 - Nov 3
$411 night

The Mastic Cana Luxury Cottage is a ground floor, 2 bedroom, 2 bath retreat set on an 11 acre private estate along the Cayman Mastic Trail on Grand Cayman’s North Side. This thoughtfully designed cottage combines modern amenities with Caribbean inspired architecture, high ceilings, and a synthetic thatch roof for a truly tropical feel. Surrounded by lush vegetation and featuring its own screened in private pool, it’s a tranquil, immersive escape—perfect for two couples or families seeking nature, privacy, and comfort. 2 Bedrooms | 2 Bathrooms | Sleeps 6 EXPERIENCE. EXPLORE. ESCAPE. The Mastic Cana Luxury Cottage at Mastic Cottages offers a warm and welcoming 2 bedroom layout that blends modern comforts with relaxed Caribbean design. High ceilings, a synthetic thatch roof, and lush landscaping create a tropical, indoor–outdoor vibe, while the layout works beautifully on its own or in combination with the nearby Mastic estate cottages for larger groups. MAIN COTTAGE ACCOMMODATION The main building is designed as a comfortable hub for cooking, dining, and relaxing. • Spacious open concept living area • Primary bedroom with king size bed and ensuite bathroom with large walk in shower • Fully equipped kitchen with modern stainless steel appliances • Dining area and cozy seating area with sofa and chaise lounge • Large flat screen smart TV with Netflix and Apple TV • Wi Fi available throughout the property SEPARATE SUITE ACCOMMODATION A covered breezeway connects the main cottage to a separate guest suite, adding privacy and flexibility. • Second bedroom with king size bed • Sitting area with queen sleeper sofa • Ensuite bathroom with spacious walk in shower • Flat screen TV in this suite as well This setup makes Cana Cottage ideal for two couples traveling together or families with older children who appreciate their own space. POOL, OUTDOOR LIVING & ENTERTAINMENT One of the highlights of Mastic Cana Cottage is its private screened in pool area and outdoor living spaces. • Screened in private pool (max depth 4 feet), reserved exclusively for Cana Cottage guests • Beach style entry for easy, relaxed use • Poolside bar and dining area for casual meals and evening cocktails • BBQ grill for outdoor cooking • Large covered palapa with comfortable seating and a hammock • Screened in porch offering a tranquil spot to unwind and enjoy the sounds of nature Inside, entertainment is easy: • Smart TVs in the living room and bedrooms with Netflix and Apple TV • Reliable Wi Fi to stay connected • Central air conditioning for comfort throughout INCLUSIONS & SERVICES Cana Cottage is stocked with practical comforts so guests can settle in quickly. • All linens provided, including bath towels and beach towels • Bathroom toiletries: shampoo, conditioner, and soap • Complimentary mid stay cleaning service for stays of seven nights or more • Complimentary bikes for guest use • Pack ’n play and high chair available on request for little ones • Parties and weddings require prior consent; please share details and obtain approval before planning events WHO THIS SUITS The Mastic Cana Luxury Cottage is especially well suited to: • Two couples who want separate sleeping spaces (main cottage + connected suite) and shared pool and living areas • Families with older children or teens who enjoy having a semi private suite connected by a breezeway • Nature lovers who want to be surrounded by greenery and close to the Mastic Trail rather than in a busy resort area • Guests seeking a quiet, character rich base that can be combined with other Mastic estate cottages for larger group stays LARGER GROUPS – ESTATE OPTIONS Have a bigger group or planning a family gathering? The connected Mastic estate properties can be combined to create flexible setups with both togetherness and privacy: • 5 bedrooms (up to 10 guests): Combine Sunnyhill Cottage (3BR) with either Mastic Chapel or Mastic Cana Cottage • 7 bedrooms (up to 14 guests): Reserve all three Mastic properties for the ultimate group retreat DINING & NEARBY AREA – NORTH SIDE & RUM POINT Old Man Bay and the North Side offer a laid back, local dining scene with some very popular spots within a short drive. VERY CLOSE (OLD MAN BAY / NORTH SIDE) • Over the Edge – Long time North Side favorite right on the water with Caribbean dishes, seafood, and a casual bar atmosphere. • The Caboose – Well reviewed local spot in Old Man Bay known for Caribbean flavors and easy, relaxed vibes. • Other local stands and cafes – Small, authentic stops for Caymanian bites along the North Side and into East End. RUM POINT & CAYMAN KAI (ABOUT 10–15 MINUTES) • Rum Point Club – Casual beachfront restaurant and bar with pizzas, beach fare, and the island famous Mudslide. • Kaibo Beach Restaurant & Upstairs Restaurant – Beachfront dining downstairs and a more refined experience upstairs, popular for sunset dinners and cocktails. You’re also within an easy drive of water based activities at Rum Point and Cayman Kai, including boat charters, snorkeling trips, and sandbar excursions. GETTING THERE Northside is roughly 30 km from Owen Roberts International Airport, typically about 30–40 minutes by car depending on traffic and stops along the way. GROCERIES, SUNDAY CLOSURES & PRACTICAL DETAILS Nearby grocery options such as Foster’s Express and Chisholm’s Grocery are about 10 minutes away by car. Larger supermarkets are also convenient stops on the drive from the airport. Supermarkets are closed on Sundays in Cayman, though most restaurants and gas stations remain open, and some gas stations sell liquor on Sundays. Grocery items can also be pre-ordered and delivered before arrival. Chisholm’s Market is on the Northside, and is open 7 days a week, and is well stocked with food, supplies, beer, wine & liquor. 10 minutes from the condo. TRANSPORTATION • A rental car is highly recommended for this area so guests can easily explore Grand Cayman at their own pace. • Many guests book directly with trusted local providers such as Marshall’s Rent-A-Car, Andy’s Rent-A-Car, or compare options through Kayak. • Due to limited public transportation in Northside, having a car offers the greatest convenience and flexibility. ACCESSIBILITY & PARKING • Accessibility: Ground floor condo • Parking: Complex parking available. PROMOTIONS Automatic discounts may apply based on travel dates, including early booking savings, and extended-stay discounts. Eligible offers are applied automatically, cannot be combined with other promotions or Repeat Guest benefits, and may be subject to blackout dates from December 17 to January 3. CHECK IN & CHECK OUT After booking, you’ll receive detailed arrival information by email, and your unique door code before arrival. Check in is any time after 4:00 PM with keyless entry; early check in may be possible depending on cleaning schedules and can be confirmed with the property manager closer to arrival. Check out is self service at 11:00 AM, with clear instructions provided; late check out is only available if pre arranged, as time is needed to prepare for incoming guests. TRAVEL INSURANCE Travel insurance is recommended, especially during hurricane season from August through October, to help protect against trip interruptions and weather-related disruptions. Mastic Chapel Cottages https://my.matterport.com/show/?m=c1fsEyHe8ZK&help=1&brand=0&nt=tab&title=0&guides=0&play=1 License number: CC-019

Villa Caymanas

North Side, KY
4 Bedrooms • 8 Guests

Oct 28 - Nov 2
$666 night

***Property Overview*** Welcome to Villa Caymanas! This beautiful oceanfront villa is located in Old Man Bay along the north coast. Boasting four full king suites, an oceanfront freshwater pool, and an expansive balcony, Villa Caymanas is the perfect vacation retreat. Whether you prefer to explore the snorkeling reefs nearby or simply relax by the pool, it’s all just steps off the back door. The beach here is strictly pebbly (rarely sandy), but the owner has a very sandy backyard around the pool deck. The villa is directly in front of Babylon, one of the top 5 dive sites on the entire island. The snorkeling in this area is excellent; however, fins or pool shoes are necessary to protect your feet. Villa Caymanas’ modern, streamlined architecture features many oversized oceanfront windows that flood the interiors with natural sunlight year-round. The kitchen, living, and dining areas open onto a second-floor balcony spanning the full width of the house, providing stunning ocean views. Guests have the option of dining indoors or al fresco off the balcony. A modern kitchen comes equipped with standard appliances, dishware, cookware, cutlery, and a coffee maker. An exercise room and home office are also on the lower level. Bedroom & Bathroom Layout (Sleeps 8 guests total) -- Bedroom 1: primary suite, upper-level, king bed, ocean views, HD cable TV, walkout access to the balcony, walk-in closet, ensuite with dual vanity and double shower. -- Bedroom 2: upper-level, king bed, garden views, HD cable TV, ensuite with shower. -- Bedroom 3: lower level, king bed, ocean views, HD cable TV, walkout access to the pool deck, ensuite with shower. -- Bedroom 4: lower level, king bed, ocean views, HD cable TV, walkout access to the pool deck, ensuite with shower. With gorgeous views throughout, comfortable furnishings, and wonderful outdoor space, Villa Caymanas is sure to please! NOTES: Bicycles and single/tandem kayaks are available for discounted rental; a signed waiver is required. ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service added to all rates. -- Accidental Damage Protection added to all rates. -- A Departure Cleaning Fee is added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays are welcome but subject to a higher cleaning fee. Please inquire to book. -- Must be 25 or older to book and must occupy the property during the entire stay. ***Property Manager Guest Services*** The 10% Guest Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Proprietary Guest benefit & discount card -- 10% advance booking discount for private charter -- Complimentary use of snorkel equipment -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors, guest services desk assistance At-Villa Benefits -- Day-after-arrival guest services follow-up -- Complimentary early check-in, if no check-out on the same day -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- Complimentary pack-n-plays, booster seats, & baby gates -- Additional kayaks available for discounted rental* *Signed waiver required. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions, which may include a partial refund or relocation. We try our best to work around Mother Nature.

The Mastic Chapel Cottage | 2BR w/ Private Pool on 11 Acre North Side Estate

North Side, Grand Cayman, KY
2 Bedrooms • 4 Guests

Oct 31 - Nov 3
$475 night

The Mastic Chapel Cottage is a unique 2 bedroom, 2 bath ground floor retreat set on an 11 acre private estate along the Cayman Mastic Trail on Grand Cayman’s North Side. This historic style chapel cottage blends modern comforts with old world charm—think vaulted ceilings, stained glass arched windows, and natural stone from the property itself. With its own private beach entry pool, lush surroundings, and access to nearby sister cottages, it’s an intimate, nature immersed escape ideal for two couples or families with older children. 2 Bedrooms | 2 Bathrooms | Sleeps 4 EXPERIENCE. EXPLORE. ESCAPE. Chapel Cottage at Mastic Cottages offers a one of a kind stay that combines history, design, and nature. Vaulted ceilings, natural stone, and historic stained glass from Keokuk, Iowa (crafted by Kokomo Glass in the late 1800s) give the space a distinctive character, while modern amenities keep it comfortable and easy to live in. A highlight of the property is the private sand entry pool, with a maximum depth of 4 feet, creating a shallow, beach like oasis just outside your door. MAIN COTTAGE ACCOMMODATION The main ground floor cottage is designed for relaxed, open concept living with easy flow between social spaces. • Spacious open plan living, dining, and kitchen area • Large primary suite with king size bed and generous ensuite bathroom • Living room with two sofas and a smart projection TV—perfect for movie nights • Modern, fully equipped kitchen with stainless steel appliances and a wine cooler SEPARATE COTTAGE ACCOMMODATION Just beside the main cottage, a smaller detached cottage adds privacy and flexibility. • Queen size bed • Flat screen smart TV • Ensuite bathroom with large walk in shower • Located next to the pool (better suited to couples or older children; not ideal for very small children who need constant supervision) The overall layout is fantastic for two couples who want both privacy and shared spaces, or families with older kids who enjoy having their own “mini cottage.” ENTERTAINMENT & COMFORT Mastic Chapel Cottage is set up for comfort, connection, and unplugging in nature—without giving up modern tech. • TVs in the living room and bedrooms with Netflix and Apple TV • Central air conditioning throughout the cottages • Wi Fi available across the property • Private sand bottom swimming pool with gentle beach style entry (exclusive to Chapel Cottage guests) • Outdoor BBQ and lounge area surrounded by native trees and greenery • Complimentary bikes for exploring the surrounding area INCLUSIONS & SERVICES You’ll arrive to a well prepared cottage with thoughtful essentials already in place. • All linens provided, including bath towels and beach towels • Bathroom toiletries: shampoo, conditioner, and soap • Pack ’n play and high chair available on request for little ones • Complimentary mid stay cleaning service for stays of seven nights or more • Parties and weddings are possible with prior consent—please share details and obtain approval before planning events Chapel Cottage offers a serene, private experience, making it ideal for guests who want a peaceful, nature focused stay rather than a traditional resort environment. WHO THIS SUITS The Mastic Chapel Cottage is especially well suited to: • Two couples who want separate sleeping spaces (main cottage + chapel cottage) and a shared pool and living area • Families with older children or teens who enjoy a bit of independence and unique spaces (separate cottage by the pool) • Nature lovers and hikers who want to be immersed in greenery, birdlife, and the Mastic Trail area rather than on a busy beach strip • Guests seeking a quiet, private, and character rich base for exploring North Side, East End, and the more untouched side of Grand Cayman LARGER GROUPS – ESTATE OPTIONS Have a bigger group or planning a family gathering? The connected Mastic estate properties can be combined to create flexible setups with both togetherness and privacy: • 5 bedrooms (up to 10 guests): Combine Sunnyhill Cottage (3BR) with either Mastic Chapel or Mastic Cana Cottage • 7 bedrooms (up to 14 guests): Reserve all three Mastic properties for the ultimate group retreat DINING & NEARBY AREA – NORTH SIDE & RUM POINT Old Man Bay and the North Side offer a laid back, local dining scene with some very popular spots within a short drive. VERY CLOSE (OLD MAN BAY / NORTH SIDE) • Over the Edge – Long time North Side favorite right on the water with Caribbean dishes, seafood, and a casual bar atmosphere. • The Caboose – Well reviewed local spot in Old Man Bay known for Caribbean flavors and easy, relaxed vibes. • Other local stands and cafes – Small, authentic stops for Caymanian bites along the North Side and into East End. RUM POINT & CAYMAN KAI (ABOUT 10–15 MINUTES) • Rum Point Club – Casual beachfront restaurant and bar with pizzas, beach fare, and the island famous Mudslide. • Kaibo Beach Restaurant & Upstairs Restaurant – Beachfront dining downstairs and a more refined experience upstairs, popular for sunset dinners and cocktails. You’re also within an easy drive of water based activities at Rum Point and Cayman Kai, including boat charters, snorkeling trips, and sandbar excursions. GETTING THERE North Side is roughly 30 km from Owen Roberts International Airport, typically about 30–40 minutes by car depending on traffic and stops along the way. GROCERIES, SUNDAY CLOSURES & PRACTICAL DETAILS Nearby grocery options such as Foster’s Express and Chisholm’s Grocery are about 10 minutes away by car. Larger supermarkets are also convenient stops on the drive from the airport. Supermarkets are closed on Sundays in Cayman, though most restaurants and gas stations remain open, and some gas stations sell liquor on Sundays. Grocery items can also be pre-ordered and delivered before arrival. Chisholm’s Market is on the North Side, and is open 7 days a week, and is well stocked with food, supplies, beer, wine & liquor. 10 minutes from the condo. TRANSPORTATION • A rental car is highly recommended for this area so guests can easily explore Grand Cayman at their own pace. • Many guests book directly with trusted local providers such as Marshall’s Rent-A-Car, Andy’s Rent-A-Car, or compare options through Kayak. • Due to limited public transportation in North Side, having a car offers the greatest convenience and flexibility. ACCESSIBILITY & PARKING • Accessibility: Ground floor condo • Parking: Complex parking available. PROMOTIONS Automatic discounts may apply based on travel dates, including early booking savings, and extended-stay discounts. Eligible offers are applied automatically, cannot be combined with other promotions or Repeat Guest benefits, and may be subject to blackout dates from December 17 to January 3. CHECK IN & CHECK OUT After booking, you’ll receive detailed arrival information by email, and your unique door code before arrival. Check in is any time after 4:00 PM with keyless entry; early check in may be possible depending on cleaning schedules and can be confirmed with the property manager closer to arrival. Check out is self service at 11:00 AM, with clear instructions provided; late check out is only available if pre arranged, as time is needed to prepare for incoming guests. TRAVEL INSURANCE Travel insurance is recommended, especially during hurricane season from August through October, to help protect against trip interruptions and weather-related disruptions. Mastic Chapel Cottages https://my.matterport.com/show/?m=c1fsEyHe8ZK&help=1&brand=0&nt=tab&title=0&guides=0&play=1 License number: CC-019

KiToCay Villa

Old Man Bay, KY
3 Bedrooms • 5 Guests

Oct 8 - 13
$454 night

***Property Overview*** Welcome to KiToCay! This 3,000 sq. ft. home is located in the village of Old Man Bay on the island’s beautiful North Side. KiToCay boasts a panoramic oceanfront living area with spectacular views, plus an over-the-water deck with a tiled cabana. Guests have compared the views and feel of this home with that of being on the bow of a cruise ship with the open ocean enveloping your senses from virtually every direction. The over-the-water deck provides access to the waters down below via a spiraling staircase. However, the best and safest way to enter the water will be from either of the sandy beach lots next door. Dubbed Toki Beach, the east lot is furnished with a hammock ringed with palm trees for guests to enjoy seaside relaxation under the shade. Guests have used this beach to host small weddings, rehearsal dinners, and private events. The snorkeling here is incredible. The reef is about 100 yards straight out from Toki Beach. We strongly recommend snorkeling along the east of the boat channel which is marked by two navigation poles. Snorkeling beyond the poles near the reef cut is risky! Powerful undercurrents can prove dangerous even for experienced snorkelers. Inside, the home’s interiors are just as impressive as any on Grand Cayman. The oceanfront living area features an open-concept design with modern decor and furniture including a plush sectional sofa, HD television, and sweeping ocean views that will take your breath away. The villa’s 3 bedrooms are spread across the upper and lower levels with the primary suite upstairs and two bedrooms downstairs. ***Sleeping Arrangements*** (Sleeps 6 adults, 8 guests max.) -- Bedroom 1: primary suite, upper-level, king bed, ocean views, walkout access to a private balcony, television, desk + chair, ensuite with double vanity and shower (bathtub removed). -- Bedroom 2: lower level, queen bed, television, shares hall bath with shower/bath combo. -- Bedroom 3: lower level, queen bed, shares hall bath with shower/bath combo. -- Additional sleeping: lower level sleeper sofa available for 2 children max. The full gourmet kitchen is a vacationing chef’s paradise. Equipped with top-of-the-line appliances--including double ovens, a gas range with grill top, and tons of counter space--guests can enjoy the comforts of a home-cooked meal away from home. Cookware, flatware, glassware, and cutlery are all provided. A small general store, Chisholm’s Grocery, is a short 5-minute drive west to stock up on foods, snacks, and drinks. For dining out, guests can walk down the street to Over the Edge Restaurant for breakfast, lunch, and dinner. KiToCay appeals to small families, traveling couples, and honeymooners. Discount rates are available for smaller groups. Notes: Single or tandem kayaks are available for discounted rental. A signed waiver is required. ==================== ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service added to all rates. -- Accidental Damage Protection added to all rates. -- A cleaning fee is added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays are subject to a higher cleaning fee. Please inquire before booking. -- Small weddings and events are permitted and require a supplemental refundable damages deposit and a minimum 7-day rental. -- Must be 25 or older to book and occupy the property during the entire stay. ***Property Manager Guest Services*** The 10% Guest Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of our Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Guest benefit & 10% discount card good at local restaurants and watersports providers -- 10% Advance Booking Discount towards a private charter -- Complimentary snorkel equipment -- Complimentary pack-n-plays, booster seats, & baby gates -- Referral to preferred vendors, guest services desk assistance -- Complimentary early check-in, if no check-out on the same day -- Kayaks available for discounted rental* *Signed waiver required. ***Nearby Points of Interest*** -- Short walk west to Over the Edge restaurant -- 1-minute drive east to the Cayman Crystal Caves -- 2 miles west to the nearest grocer, Chisholm’s Grocery -- 2.5 miles from our Welcome Center -- 6.4 miles west to the Rum Point Club and Bioluminescent Bay -- 7.4 miles to the Kaibo Beach Bar & Grill and Starfish Point -- 6.2 miles east to the nearest supermarket, Foster’s Express, plus The Italian Kitchen, and two beach resorts, Morritt’s and The Reef. -- 8.5 miles to Tukka East Restaurant & Bar and the Cayman Parrot Sanctuary -- 9.3 miles to La Casita Taco & Tequilla Bar -- 20 miles (40-minute drive) to Owen Roberts Airport (GCM) ***Getting Around*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Avis, or Marshalls. =================== ***Villa Cleaning & Sanitation*** All villas are cleaned and sanitized before each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. We try our best to work around Mother Nature.

The Mastic Cottage Collection | 7BR Estate on North Side

North Side, Grand Cayman, KY
7 Bedrooms • 14 Guests

Oct 31 - Nov 3
$1,295 night

The Mastic Cottage Collection is a private 7 bedroom, 6.5 bath estate on Grand Cayman’s peaceful North Side, combining three distinct cottages—Chapel, Cana, and Sunnyhill—across 11 lush acres. Designed for multi family vacations, reunions, and small retreats, this ground floor collection sleeps up to 14 guests and offers a tranquil, nature immersed setting just a short stroll from the Caribbean Sea and uncrowded beaches. With private pools, tropical architecture, and shared trails and outdoor spaces, it’s an exceptional choice for groups seeking privacy, space, and a slower island pace. ESTATE OVERVIEW THE MASTIC COTTAGE COLLECTION – 7 Bedrooms | 6.5 Bathrooms | Sleeps 14 Your exclusive estate includes: • Mastic Sunnyhill Cottage – 3 bedrooms, 2.5 bathrooms • Mastic Chapel Cottage – 2 bedrooms, 2 bathrooms • Mastic Cana Cottage – 2 bedrooms, 2 bathrooms Set within an 11 acre private, gated estate just off the Cayman Mastic Trail, the property is surrounded by native trees, birdlife, and walking paths. Guests can enjoy a private nature trail on the grounds, then venture out to explore the nearby Mastic Trail, North Side coastline, and beaches. The layout is ideal for larger families, multi generational trips, and groups who want to be together but still enjoy their own cottages and pools. EXPLORE THE COTTAGES THE MASTIC CHAPEL COTTAGE – 2BR | 2BA Chapel Cottage blends modern comfort with a unique, chapel inspired design. • Ground floor main cottage with open concept living, dining, and fully equipped kitchen (stainless appliances + wine cooler) • Large primary suite with king size bed and ensuite bathroom • Separate smaller cottage nearby with queen size bed, flat screen TV, and ensuite bath—ideal for a second couple or older children • Smart projection TV in living room, Netflix and Apple TV, central A/C, and Wi Fi • Private sand entry pool (up to 4 ft deep), BBQ, lounge area, and complimentary bikes Perfect for: two couples traveling together or families with older kids who want a mix of privacy and shared spaces. THE MASTIC CANA COTTAGE – 2BR | 2BA Cana Cottage combines Caribbean inspired architecture with modern amenities and a strong indoor–outdoor feel. • Main cottage with high ceilings, synthetic thatch roof, and tropical ambience • Primary bedroom with king size bed and ensuite bath with walk in shower • Open concept kitchen with stainless appliances, dining area, and cozy seating with large smart TV (Netflix, Apple TV) • Separate suite connected via covered breezeway: king size bed, queen sleeper sofa, ensuite bath, and its own TV • Screened in private pool (max depth 4 ft) with poolside bar, BBQ grill, hammock, covered palapa, and outdoor dining/seating • Wi Fi and complimentary bikes for exploring Perfect for: two couples, or a couple plus older children/teens who appreciate their own suite. THE MASTIC SUNNYHILL COTTAGE – 3BR | 2.5BA Sunnyhill is the main “family cottage,” with a more traditional home layout and flexible sleeping. • Primary bedroom with king size bed, flat screen smart TV, dressing room, and ensuite bath with walk in shower • Second bedroom with queen size bed • Third bedroom with twin bunk beds, ideal for children or two individuals sharing • Shared bathroom with walk in shower for bedrooms two and three • Additional half bath off the main living area • Den/office space for remote work or a quiet reading corner The main living area features: • Fully equipped modern kitchen • Comfortable living room with smart TV (Netflix, Apple TV) • Central air conditioning and Wi Fi throughout • Outdoor BBQ and lounge areas surrounded by tropical landscaping Perfect for: families with children, or the “hub” cottage for the group. AMENITIES & INCLUSIONS Each cottage is thoughtfully outfitted so large groups can focus on relaxing, not logistics. ACROSS THE ESTATE YOU’LL FIND: • High quality furnishings and linens • Bath towels and beach towels • Bathroom amenities: shampoo, conditioner, and soap • Fully equipped kitchens with stainless steel appliances • Air conditioning and Wi Fi • Smart TVs with Netflix and Apple TV in living rooms and primary bedrooms • Outdoor seating areas for relaxation and al fresco dining • BBQ grills and shaded lounging spaces • Complimentary bikes for guest use SERVICES & EXTRAS • Complimentary mid stay cleaning service for stays of seven nights or more • Children welcome; pack ’n play and high chair available on request • Parties and weddings require prior consent—please share details and obtain approval before planning events on the estate WHY CHOOSE THE MASTIC COTTAGE COLLECTION? This collection is designed for extended families, multi family groups, and friends traveling together who want: • Separate, self contained cottages for privacy, each with its own character and amenities • Shared outdoor spaces and private pools (for Chapel and Cana) that are close enough for connection but not on top of each other • A quiet, nature rich setting away from resort crowds, while still being a short drive to North Side and East End beaches and attractions • Flexible layouts that can accommodate up to 14 guests comfortably across 7 bedrooms DINING & NEARBY AREA – NORTH SIDE & RUM POINT Old Man Bay and the North Side offer a laid back, local dining scene with some very popular spots within a short drive. VERY CLOSE (OLD MAN BAY / NORTH SIDE) • Over the Edge – Long time North Side favorite right on the water with Caribbean dishes, seafood, and a casual bar atmosphere. • The Caboose – Well reviewed local spot in Old Man Bay known for Caribbean flavors and easy, relaxed vibes. • Other local stands and cafes – Small, authentic stops for Caymanian bites along the North Side and into East End. RUM POINT & CAYMAN KAI (ABOUT 10–15 MINUTES) • Rum Point Club – Casual beachfront restaurant and bar with pizzas, beach fare, and the island famous Mudslide. • Kaibo Beach Restaurant & Upstairs Restaurant – Beachfront dining downstairs and a more refined experience upstairs, popular for sunset dinners and cocktails. You’re also within an easy drive of water based activities at Rum Point and Cayman Kai, including boat charters, snorkeling trips, and sandbar excursions. GETTING THERE Northside is roughly 30 km from Owen Roberts International Airport, typically about 30–40 minutes by car depending on traffic and stops along the way. GROCERIES, SUNDAY CLOSURES & PRACTICAL DETAILS Nearby grocery options such as Foster’s Express and Chisholm’s Grocery are about 10 minutes away by car. Larger supermarkets are also convenient stops on the drive from the airport. Supermarkets are closed on Sundays in Cayman, though most restaurants and gas stations remain open, and some gas stations sell liquor on Sundays. Grocery items can also be pre-ordered and delivered before arrival. Chisholm’s Market is on the Northside, and is open 7 days a week, and is well stocked with food, supplies, beer, wine & liquor. 10 minutes from the condo. TRANSPORTATION • A rental car is highly recommended for this area so guests can easily explore Grand Cayman at their own pace. • Many guests book directly with trusted local providers such as Marshall’s Rent-A-Car, Andy’s Rent-A-Car, or compare options through Kayak. • Due to limited public transportation in Northside, having a car offers the greatest convenience and flexibility. ACCESSIBILITY & PARKING • Accessibility: Ground floor condo complex • Parking: Complex parking available. CHECK IN & CHECK OUT After booking, you’ll receive detailed arrival information by email, and your unique door code before arrival. Check in is any time after 4:00 PM with keyless entry; early check in may be possible depending on cleaning schedules and can be confirmed with the property manager closer to arrival. Check out is self service at 11:00 AM, with clear instructions provided; late check out is only available if pre arranged, as time is needed to prepare for incoming guests. TRAVEL INSURANCE Travel insurance is recommended, especially during hurricane season from August through October, to help protect against trip interruptions and weather-related disruptions. Mastic Chapel Cottages https://my.matterport.com/show/?m=PjLFDjYzi2u&help=1&brand=0&nt=tab&title=0&guides=0&play=1 License number: CC-019

Fischers Reef

Rum Point, KY
8 Bedrooms • 20 Guests

Dec 12 - 19
$5,169 night

***Property Overview*** Located just a mile from the famous Rum Point Club, Fischer’s Reef is a perfectly designed 8-bedroom oceanfront villa ideal for large families or group getaways. The villa’s unique floor plan allows guests to spread out in ample style with multiple living and sleeping areas. A wide staircase separates the floors meaning the noise from one floor won’t reach the others. Renovations completed include luxurious features such as an oceanfront infinity pool with optional heat, beach cabana, multiple indoor and outdoor dining areas, two separate 75-inch LED TVs, and a Sonos home theater system. For remote working professionals, a new high-speed fiber internet connection has been wired to the property. Multiple users and devices can now connect to the web to work or learn remotely with reliable speeds and increased bandwidth. All the attention to detail makes Fischer’s Reef a wonderful venue for entertaining and relaxation. ***Bedroom & Bathroom Layout*** (Sleeps 18 guests total, 14 adults max) -- King Suite #1: Main-level suite with a king bed, garden views, and an ensuite bath. -- King Suite #2: Main-level suite with a king bed, partial ocean views, and an ensuite bath. -- King Suite #3: Pool-level suite with a king bed, ocean views, and an ensuite bath. -- Queen Suite #1: Pool-level suite with a queen bed, ocean views, and an ensuite bath. -- Queen Suite #2: Pool-level suite with a queen bed, ocean views, and an ensuite bath. -- Queen Suite #3: Pool-level suite with a queen bed, garden views, and an ensuite bath with a shower tub combo. -- Twin Bunk Suite: Pool-level suite with two sets of twin over twin bunk beds and an ensuite bath with a shower tub combo. -- The living area also has a sleeper sofa. ***Fischer’s Reef Notable Amenities*** -- Fischer’s Reef is located within a designated marine park teeming with abundant marine life just steps off the infinity pool. Strap on your snorkel gear and go exploring, but please wear pool shoes for protection and avoid damaging the corals! -- Sandy beach with oceanside cabana and hammocks for hours of relaxing by the sea -- Wonderful sunrises and plenty of privacy -- Spectacular stargazing with minimal light interference -- The indoor living and dining areas upstairs are furnished with high-quality upholstered furniture and decor -- Large modern kitchen on the upper level with a spacious refrigerator, small upright freezer, gas range, microwave, two dishwashers, wine fridge, drip coffee makers, a Keurig, a Nespresso, and ample counter space -- Breakfast table for 8 and two large dining room tables seats 20; both with ocean views -- Oversized great room with multiple couches and living areas allow room for large families to spread out -- Exterior spiral staircase connects the balcony with the pool deck while providing wonderful elevated views of the beach and reef -- Pool-level living area features a kitchenette with a coffee center and microwave, dining table with seating for 6, plus a 75" LED TV for movies, games and sporting events -- Blu-Ray player and Apple TV on each level -- Laundry rooms upstairs and downstairs -- Fiber optic wifi connection with increased speed for multiple device streaming -- 7-zone central air conditioning -- Heated pool set to 88 degrees; additional heat to 88-92 degrees available during winter months for $500/week surcharge -- Home security system available -- Small deposit safe for guest valuables -- 1 single kayak & 1 tandem kayak included with the villa -- Additional tandem kayaks are available for discounted rental. Signed waiver is required. A local professional property manager resides on-site in the small cottage near the gated entrance. Manager’s cottage is heavily landscaped and separated from the villa. Close enough to reach out in case of emergency, but far enough away so as to respect your privacy. Owner requires Saturday-to-Saturday bookings unless otherwise pre-approved. ============== ***Rate Details*** -- 13% Occupancy Tax is added to all rates. -- 12.90% Villa Concierge & Service Fee is added to all rates. -- A Departure Cleaning Fee is added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire with your travel dates prior to booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 years or older to book and must occupy the property during the entire stay. -- Check-in is at 3:00 pm. -- Check-out is at 10:00 am. ***Property Manager Guest Services*** The Villa Concierge & Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Proprietary Guest benefit & discount card -- 10% advance booking discount for private charter -- Complimentary use of snorkel equipment -- Guest parcel receipt & hold for check-in -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Airport arrival Fast-Track VIP Process (fee charged by CAA) -- Arrange airport pick-up & rental vehicles (fee applies) -- Special event/dinner reservations At-Villa Benefits -- Welcome amenity basket/arrangement -- Complimentary early check-in, if no check-out on the same day -- Day-after-arrival & mid-week guest services follow-up -- Complimentary use of Apple TVs, BlueTooth speakers, beverage coolers -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- $2,500 of Accidental Villa Damage Protection -- Complimentary pack-n-plays, booster seats, & baby gates -- Additional kayaks available for discounted rental* *Signed waiver required. ============ ***Villa Cleaning & Sanitation*** All villas are cleaned and sanitized prior to each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. We try our best to work around Mother Nature.

Twin Palms

Rum Point, KY
7 Bedrooms • 14 Guests

Oct 8 - 13
$1,834 night

***Property Overview*** Twin Palms is directly oceanfront in the Rum Point district and enjoys a sandy beach and protective coral reef with excellent snorkeling. No neighbors on either side ensure guest privacy. This deceptively large 6,500 sq ft single-story home was built specifically for entertaining larger families. Twin Palms offers stunning ocean views with a modern open-concept design. The main house spans 6 bedrooms and 4.5 baths and includes an attached king studio suite with a private bath and kitchenette. This studio suite is ideal for nannies, grandparents, etc. The studio suite is accessible from the exterior as well as through the laundry room. ***Twin Palms Unique Features*** -- 100’ oceanfront covered veranda for protection from the sun. -- 56’ pool with integral heated infinity edge spa, LED lighting. -- Pool Table, Foosball, and Shuffle Board in the game room -- 2 kayaks available for rental -- Veranda offers an exterior half-bath so that guests need not walk inside as often with sand on their feet. -- Large, modern kitchen with breakfast bar, stainless steel appliances, 2 dishwashers (easy cleanup!), and tons of counter space for feeding a large group. -- Media room with large flatscreen TV, plenty of comfortable seating, and lots of tech-toys (Xbox One, Sonos, Apple TV, etc.) -- Multiple dining areas, all with gorgeous oceanfront views. Outdoor dining tables delivered in February. -- The main living area and media room each offer multiple reclining seat choices for watching sports, movies, or gaming. -- Large custom-made charcoal grill (guest needs to purchase charcoal) ***Twin Palm’s Sleeping Arrangements*** (Sleeps 16 guests total) -- Oceanfront Master Suite #1 - stunning ocean views, king bed, sliding glass doors to the pool deck, TV, and an ensuite bath with a walk-in shower. -- Oceanfront Master Suite #2 - stunning ocean views, king bed, sliding glass doors to the pool deck, and an ensuite bath with a walk-in shower. -- King Studio Suite - king suite with a kitchenette (oven, full-sized fridge, and microwave) and an ensuite bath with a combination tub/shower. -- Queen Bedroom #1 - queen bed, garden views, and shares a bathroom with Twin Bedroom #1 -- Twin Bedroom #1 - two twin over full bunk beds, garden views, and shares a bathroom with Queen Bedroom #1 -- Queen Bedroom #2 - queen bed, garden views, and shares a bathroom with Twin Bedroom #2 -- Twin Bedroom #2 - two twin beds, garden views, and shares a bathroom with Queen Bedroom #2 The owner does not charge an extra fee for spa heat. The pool itself is not heated; even the Ritz-Carlton and Westin hotels do not heat their pools in winter this far south. Weddings and events are permitted. An event fee and an additional refundable damage deposit apply. Notes: Additional kayaks are available for discounted rental. Signed waiver is required. ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 12.90% Villa Concierge & Service Fee is added to all rates. -- A Cleaning Fee is added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Weddings and events with a max of 50 guests permitted with prior written approval and a nonrefundable $2,500 event fee -- Must be 25 or older to book and must occupy the property during the entire stay. -- Check-in is at 3:00 pm. -- Check-out is at 10:00 am. ***Property Manager Guest Services*** The following perks are provided throughout your stay. Member Benefits -- Complimentary use of snorkel equipment -- Complimentary pack-n-plays, booster seats, & baby gates -- 10% Early Bird Discount towards a private charter -- Exclusive 10% guest discount card good at local restaurants and businesses -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Guest parcel receipt & hold for check-in -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors, guest services desk assistance -- Airport arrival Fast-Track VIP Process (fee charged by CAA) -- Special event/dinner reservations At-Villa Benefits -- Welcome amenity basket -- Complimentary early check-in, if no check-out on the same day -- Day-after-arrival guest services follow-up -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- $2,500 of Accidental Villa Damage Protection -- Additional kayaks available for discounted rental* *Signed waiver required. ***Beach Notes*** All beaches in Grand Cayman are technically public, since the Crown extends to the high-water mark. Be advised that the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked before your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions, which may include a partial refund or relocation. We try our best to work around Mother Nature.

Cayman Sands

Old Man Bay, KY
5 Bedrooms • 14 Guests

Oct 8 - 13
$914 night

***Property Overview*** Cayman Sands is an oceanfront villa in Old Man Bay along the north coast. This popular villa is one of only 2-3 homes that offer shore scuba diving off the famous Cayman Wall. With an open, one-story design, Cayman Sands offers guests an intimate experience across 4,000 sq ft. of living space, plus a one-bedroom guest cottage. The main house features 4 bedroom suites (king, queen, 2 twin beds, and 4 bunk beds) with ensuite baths that have been completely re-tiled and renovated. For parties with more than 4 adult guests, the 2 twin beds can be converted to a king upon request. Both oceanfront suites have french doors that open up onto the screened pool atrium and sun deck. Cayman Sands was thoughtfully designed to be opened up on cool winter nights when A/C isn’t necessary. The oceanfront freshwater pool is protected by a screened atrium keeping local wildlife and insects at bay from ruining your stay. Optional pool heat is available in the winter months for an additional surcharge. The pool atrium comes furnished with a sectional sofa and dining table perfect for evening cocktails or outdoor dining. The view of the large sandy beach is framed by the two wings of the house, an oceanfront gazebo, and two hammocks ideal for long afternoons relaxing with a book or simply enjoying the views. An oceanfront vaulted great room floods the villa with natural light and stunning views through 30 feet of sliding glass doors. A recently upgraded kitchen offers all the modern appliances you would expect, as well as dishware, cookware, and cutlery. The living area is furnished with a wall-mounted flat-screen TV, plush couches, and a sleeper sofa for small children only. ***Bedroom & Bathroom Layout*** (Sleeps 10 adults max., 14 guests total) -- Primary Suite: ocean views, king bed, desk + chair, walkout access to the pool atrium and sun deck, footpath to the ocean gazebo, ensuite with shower and water wand. -- Queen Suite: ocean views, queen bed, desk + chair, walkout access to the pool atrium and sun deck, ensuite with shower. -- Twin Suite: garden views, 2 twin beds, ensuite with shower bath; Beds can be fitted into a king bed upon request. -- Bunk Suite: garden views, 2 sets of bunk beds, ensuite with a shower bath. -- Guest Cottage: detached cottage, queen bed, kitchenette, television, screened porch, ensuite with shower. -- Additional Sleeping: sleeper sofa in the TV den for small children only. The guest cottage is NEVER rented separately to unrelated guests during your stay--it is there if you need it. ================= ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service added to all rates. -- Accidental Damage Protection added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire with your travel dates prior to booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 or older to book and must occupy the property during the entire stay. ***Property Manager Guest Services*** The 10% Guest Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Proprietary Guest benefit & discount card -- 10% advance booking discount for private charter -- Complimentary use of snorkel equipment -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors, guest services desk assistance At-Villa Benefits -- Day-after-arrival guest services follow-up -- Complimentary early check-in, if no check out on the same day -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- Complimentary pack-n-plays, booster seats, & baby gates -- Additional kayaks available for discounted rental* *Signed waiver required. ================== ***Villa Cleaning & Sanitation*** All villas are cleaned and sanitized prior to each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum seaweed seasonally. Sargassum is a harmless seaweed that has increased in frequency over the summer months. Our owners do make efforts to remove heavy sargassum and will have the beach raked before your arrival. We try our best to work around Mother Nature.

Spacious 3-Bedroom 3-Bathroom Beachfront Condo with Heated Pool

North Side, North Side, KY
3 Bedrooms • 6 Guests

Feb 6 - 12
$525 night

Tranquility in the Tropics, relax by the pool or dig your toes into the white sand beach catching some rays! This is what you’ll find greeting you at On the Bay! Enjoy our comfortable slice of heaven on Cayman’s lush North Side. The view from your balcony is priceless, the sound of the waves waking you up in the morning is surreal. This 3-bedroom beachfront condominium located in Old Man Bay on the North Side of Grand Cayman exudes the charm of traditional Caribbean architecture. The interiors are adorned with rustic wooden furnishings and artisanal decor that creates a cozy and inviting atmosphere. Each bedroom is furnished with plush beds and premium linens that offer ultimate comfort, while the living area boasts stunning ocean views and plush seating. Each bedroom in this house comes equipped with its own bathroom for added convenience. As you enter the master bedroom, you’ll be greeted by a spacious and elegant room with a king-sized bed. Connected to the master bedroom is a private bathroom that boasts a jetted tub. You can indulge in a soothing soak after a long day, as the tub is designed to provide an exquisite spa-like experience. Moving on to the second bedroom, you’ll find a comfortable queen-sized bed awaiting you. Adjacent to the second bedroom is its dedicated bathroom, ensuring privacy and convenience for its occupants. In the third bedroom of this house, you’ll find a cozy double bed, perfect for a comfortable night’s sleep. The room also has its own dedicated bathroom. The fully equipped kitchen features modern appliances and all the essential cookware and utensils for preparing delicious meals, while the spacious balcony offers breathtaking views of the turquoise waters and gentle sea breeze. Entire condo, shared heated pool and beach. To fully embrace the serene ambiance of the North Side, we recommend renting a car for convenient transportation, as public options may be limited. With George Town approximately 50 minutes away, having a car will grant you the freedom to explore the area’s hidden treasures and embrace the picturesque beauty at your own leisurely pace. A restaurant, bar, liquor store and gas station are within walking distance. If the booking website does not collect it directly, a refundable security deposit of US$500 will be collected by the property prior to your stay. We reserve the right to substitute equal or better accommodation in the event of a double booking or if the rental is unavailable for any reason, including but not limited to sale or repair.

On the Bay #103 | Oceanfront 3BR Condo | Old Man Bay, North Side

North Side, North Side, KY
3 Bedrooms • 6 Guests

Dec 3 - 6
$339 night

On the Bay #103 is a bright, ground floor 3 bedroom, 3 bath condo set in a lush, tropical beachfront resort in Old Man Bay on Grand Cayman’s North Side. With views of the gardens and sea, a private patio, direct access to the resort pool, and a protected swimming cove just steps away, it offers a peaceful alternative to Seven Mile Beach while still being within about 10 minutes of Rum Point and nearby dining. It’s ideal for families or small groups looking for island tranquility, snorkeling, and easy access to North Side and Rum Point attractions. 3 Bedrooms | 3 Bathrooms | Sleeps 6 LIVING AREA & INTERIOR FEATURES The condo has a relaxed, coastal feel with everything you need for a comfortable stay. • Newly furnished interior with an open plan layout • Fully equipped kitchen with stainless steel appliances • Drip coffee maker and complete cookware/utensils for home cooked meals • Spacious living area with a large flat panel HDTV and comfortable seating • Sliding doors leading to a breezy garden level patio with views of the pool and ocean • In unit washer and dryer for added convenience BEDROOMS & BATHROOMS On the Bay #103 comfortably sleeps up to 6 guests across three well appointed bedrooms and three full bathrooms. • Primary bedroom: king size bed, ensuite bathroom, flat screen TV • Second bedroom: queen size bed • Third bedroom: two twin beds, ideal for kids or friends • Fresh linens and ample closet space in each room STARTER ESSENTIALS Guests are welcomed with a comprehensive starter pack including dishwashing liquid, dishwasher detergent, laundry detergent, shampoo, conditioner, hand soap, toilet paper, paper towels, and coffee filters. Linens, bath towels, beach towels, a blow dryer, and an iron with board are also provided, along with charcoal bags and utensils for the BBQ. BEACH & OUTDOOR AMENITIES This small resort is designed for relaxed days by the water, with a natural, North Side feel. • Large oceanfront freshwater pool with loungers and a shaded gazebo • Beachfront area with a natural cove offering calm water for swimming and snorkeling, especially good for children • Rocky shoreline in places—water shoes are recommended for comfort and footing • Communal charcoal BBQ grill near the pool/beach for casual outdoor cooking The protected cove and reef offshore make this a great spot for those who enjoy snorkeling, floating, and simply unwinding by the sea away from the busier areas of the island. BEACH CONDITIONS Properties on the North Side and East End of Grand Cayman may occasionally see sargassum (seaweed) wash ashore, mostly between May and August. This is a natural, seasonal occurrence throughout the Caribbean, and conditions can vary day to day. Grand Cayman offers gorgeous beaches, great snorkeling, and plenty to enjoy island-wide, so we don’t anticipate it impacting your trip, just a heads-up in case you notice it during your visit. DINING & NEARBY AREA – NORTH SIDE & RUM POINT Old Man Bay and the North Side offer a laid back, local dining scene with some very popular spots within a short drive. VERY CLOSE (OLD MAN BAY / NORTH SIDE) • Over the Edge – Long time North Side favorite right on the water with Caribbean dishes, seafood, and a casual bar atmosphere. • The Caboose – Well reviewed local spot in Old Man Bay known for Caribbean flavors and easy, relaxed vibes. • Other local stands and cafes – Small, authentic stops for Caymanian bites along the North Side and into East End. RUM POINT & CAYMAN KAI (ABOUT 10–15 MINUTES) • Rum Point Club – Casual beachfront restaurant and bar with pizzas, beach fare, and the island famous Mudslide. • Kaibo Beach Restaurant & Upstairs Restaurant – Beachfront dining downstairs and a more refined experience upstairs, popular for sunset dinners and cocktails. You’re also within an easy drive of water based activities at Rum Point and Cayman Kai, including boat charters, snorkeling trips, and sandbar excursions. GETTING THERE Old Man Bay is roughly 30 km from Owen Roberts International Airport, typically about 30–40 minutes by car depending on traffic and stops along the way. WHO THIS SUITS On the Bay #103 is a great match for guests who want a quieter, more natural setting without being far from well known North Side attractions. • Families with children who will appreciate the ground floor access, pool, and protected swimming cove. • Snorkelers and ocean lovers who prefer a reefy, more natural shoreline over a fully manicured resort beach. • Couples or small groups looking for a calm alternative to Seven Mile Beach, while staying within a short drive of Rum Point and Cayman Kai. • Guests planning longer stays who value a full kitchen, in unit laundry, and a laid back residential resort feel. GROCERIES, SUNDAY CLOSURES & PRACTICAL DETAILS Nearby grocery options such as Foster’s Express and Chisholm’s Grocery are about 10 minutes away by car. Larger supermarkets are also convenient stops on the drive from the airport. Supermarkets are closed on Sundays in Cayman, though most restaurants and gas stations remain open, and some gas stations sell liquor on Sundays. Grocery items can also be pre-ordered and delivered before arrival. Chisholm’s Market is on the Northside, and is open 7 days a week, and is well stocked with food, supplies, beer, wine & liquor. 10 minutes from the condo. TRANSPORTATION • A rental car is highly recommended for this area so guests can easily explore Grand Cayman at their own pace. • Many guests book directly with trusted local providers such as Marshall’s Rent-A-Car, Andy’s Rent-A-Car, or compare options through Kayak. • Due to limited public transportation in Northside, having a car offers the greatest convenience and flexibility. ACCESSIBILITY & PARKING • Accessibility: Ground floor condo • Parking: Complex parking available. PROMOTIONS Automatic discounts may apply based on travel dates, including seasonal Stay 7, Pay 6 offers from May 1 to November 1, along with last-minute deals, early booking savings, and extended-stay discounts. Eligible offers are applied automatically, cannot be combined with other promotions or Repeat Guest benefits, and may be subject to blackout dates from December 17 to January 3. CHECK IN & CHECK OUT After booking, you’ll receive detailed arrival information by email, and your unique door code before arrival. Check in is any time after 4:00 PM with keyless entry; early check in may be possible depending on cleaning schedules and can be confirmed with the property manager closer to arrival. Check out is self service at 11:00 AM, with clear instructions provided; late check out is only available if pre arranged, as time is needed to prepare for incoming guests. TRAVEL INSURANCE Travel insurance is recommended, especially during hurricane season from August through October, to help protect against trip interruptions and weather-related disruptions. Stay 7 Pay 6 On the Bay License number: GH-167

Olympus Villa

Rum Point, KY
5 Bedrooms • 12 Guests

Oct 14 - 19
$1,374 night

***Property Overview*** Welcome to Olympus, a landmark oceanfront estate in Rum Point. Recently acquired by new owners, this striking, architect-designed villa sits on an elevated shoreline, offering panoramic views of reef-protected waters and direct access to world-class snorkeling. With a bold abstract design, a three-level layout, and seamless indoor-outdoor living, Olympus is a masterpiece of modern island luxury. The heart of the home is the main-level great room, where 40 feet of floor-to-ceiling sliding glass opens to a sun-drenched terrace and L-shaped freshwater pool. The pool, heated seasonally from Thanksgiving through mid-April, is flanked by tiled patios and cool artificial turf for barefoot comfort. The home’s angular design provides natural shade throughout the day, creating relaxing outdoor retreats. A sandy backyard stretches to the water’s edge, while a half-bath with exterior entry serves guests enjoying the pool. Indoors, a floating staircase and tropical wood accents lead into a stylish, open-concept space. The living area features a sectional sofa, large HD cable television with Apple TV for streaming, and a PS4, plus an adjacent reading nook for quieter moments. Hidden roll-down shades and five independent A/C zones ensure comfort throughout. The expansive kitchen boasts quartz countertops, top-of-the-line appliances, and a large island ideal for chef-hosted dinners or casual meals. A breakfast bar seats four, while the main dining table accommodates ten. Five well-appointed bedrooms sleep up to 12 guests, 10 adults max. There’s a family suite and bunk room on the lower level, plus three king suites on the upper level. *Sleeping Arrangements* (Sleeps 12 guests total, 10 adults max) -- Bedroom 1: family suite, lower level, king bed, sleeper sofa for 2 small children, television, walkout access to the pool deck, coffee station with minifridge, ensuite with shower. -- Bedroom 2: lower level, twin-over-full bunk bed, television, uses adjacent half bathroom. -- Bedroom 3: primary suite, upper level, floor-to-ceiling oceanfront windows, king bed, television, desk + chair, walkout access to the east + west terraces, ensuite with soaking tub and rainfall shower. -- Bedroom 4: upper level, king bed, television, walkout access to the west terrace, ensuite with shower. -- Bedroom 5: upper level, king bed, television, walkout access to the west terrace, makeup vanity, ensuite with shower. The third-floor rooftop terrace elevates outdoor living with 360-degree island views, an alfresco dining veranda seating 8–10 people, plus a sun deck for daytime tanning and a lounge area for late-night stargazing. An outdoor prep kitchen makes sunset dinners unforgettable. Additional amenities include a private home office with wifi, a full laundry room with detergent and extra linens, a propane Rinnai water system for continuous hot water, two propane grills, and heavy tropical landscaping for privacy. A home security system is available upon request, and mid-week housekeeping is included with 7-night stays. Whether relaxing poolside, enjoying a surf-n-turf cookout on the beach, or late-night stargazing from the rooftop terrace, Olympus offers a one-of-a-kind Cayman experience designed for privacy, comfort, and spectacular views. ========= ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 12.90% Villa Concierge & Service Fee is added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays are welcome but subject to a higher cleaning fee. Please inquire to book. -- Must be 25 years or older to book and must occupy the villa during the entire rental period. -- Check-in is at 3:00 pm; check-out is at 10:00 am. ***Property Manager Guest Services*** The Villa Concierge & Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island Guest Services Team & Welcome Center -- Free snorkel gear for all members of your group -- Free access to our private fitness center (18+ yrs.) -- Complimentary business center access: computers, printer, scanner, & FedEx/DHL supplies -- Guest benefit card for 10% discounts at select restaurants and preferred vendors -- 10% Discount towards a private Stingray City snorkel charter -- Guest parcel receipt & hold for check-in -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Airport arrival Fast-Track VIP Process (fee charged by CAA) -- Arrange airport pick-up & rental vehicles (fee applies) -- Special event coordination and dinner reservations At-Villa Benefits -- Welcome amenity basket with locally sourced goods -- Free baby gear including pack-n-plays, booster seats, & baby gates -- Complimentary use of Apple TVs, Bluetooth speakers, beach coolers, and more -- Complimentary early check-in, if no check-out on the same day -- Day-after-arrival & mid-week guest services follow-up -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- $2,500 of Accidental Villa Damage Protection -- Additional kayaks available for discounted rental* *Signed waiver required. =================== ***Villa Cleaning & Sanitation*** All villas are cleaned and sanitized before each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum. Sargassum is a harmless seaweed that is largely seasonal in the summer months. Our owners will remove heavy sargassum and will have the beach raked ahead of your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions, which may include a partial refund or relocation. We try our best to work around Mother Nature.

Halcyon Point

Old Man Bay, KY
5 Bedrooms • 10 Guests

Oct 8 - 12
$1,374 night

***PROPERTY DESCRIPTION*** Welcome to Halcyon Point, a newly constructed 5-bedroom luxury villa with modern architecture set on the oceanfront in the North Side. With over 200 feet of beachfront and breathtaking ocean views from every room, this villa offers an unparalleled Caribbean getaway. Designed for relaxation and refined living, Halcyon Point combines modern elegance with the island’s natural beauty, creating the perfect escape for families or groups seeking privacy and serenity. The villa’s interiors feature an open-concept design, with expansive front-and-rear windows and doors that fill the space with natural light and perfectly frame the sparkling Caribbean vistas. 16 feet of sliding glass on both the landside and oceanside can allow a wonderful cross-breeze in the cooler months. A gourmet kitchen with modern appliances suitable for an in-villa chef makes meal preparation effortless, whether enjoying a casual breakfast indoors or grilling fresh local seafood on a built-in propane grill by the pool. Step outside onto your private oasis, where a large private pool with a convenient half-bath and an inviting built-in spa await. Optional spa heat is available for $25 per day. Surrounded by lush tropical landscaping, the large veranda includes enough space for your entire group to spread out and relax. Comfortable outdoor seating, loungers, and dining areas provide the ideal setting for savoring sunsets and ocean breezes. Halcyon Point boasts five spacious bedroom suites, including four luxurious primary suites. All bedrooms and ensuites have ocean views, and 4 bedrooms have walk-out access to the beach or a shared balcony with stairs to the beach and pool deck below. This thoughtful design ensures every guest enjoys privacy, comfort, and convenience. ***Sleeping Arrangements*** (Sleeps 10 guests total) -- Bedroom 1: first primary suite, lower level, king bed, ocean views, walkout access to the beach or pool deck, ensuite with shower. -- Bedroom 2: second primary suite, lower level, king bed, ocean views, walkout access to the beach or pool deck, ensuite with shower. -- Bedroom 3: lower level, two XL twin beds, ocean view, television, ensuite with shower; twin beds can be fitted into a king as pictured upon request. -- Bedroom 4: third primary suite, upper level, king bed, ocean views, television, walk-out access to a shared ocean balcony and tanning terrace, ensuite with dual vanity, soaking tub, and separate shower. -- Bedroom 5: fourth primary suite, upper level, king bed, ocean views, television, walk-out access to a shared ocean balcony and tanning terrace, ensuite with dual vanity, soaking tub, and separate shower. Located in the serene North Side, this villa provides direct access to exceptional snorkeling and diving reefs, as well as excellent surf-fishing. For those looking to explore beyond the beach, nearby attractions like the Cayman Crystal Caves, the Queen’s Botanical Park, the Rum Point Club, and the East End offer unique island experiences just a short drive away. Half a mile west of the villa is a public dock and boat ramp for boat or jet-ski pickups. Whether you’re lounging poolside, soaking in the spa, taking a dip in the ocean, or discovering the natural wonders of Grand Cayman, Halcyon Point promises an unforgettable blend of luxury and tranquility for discerning travelers. *Note: A Cleaning Fee is added to all stays due to enhanced cleaning and sanitation practices. **Additional tandem kayaks are available for discounted rental. A signed waiver is required. ======= ***RATE DETAILS*** -- 13% Occupancy Tax added to all rates. -- 12.90% Villa Concierge & Service Fee added to all rates. -- A Departure Cleaning Fee is added for all stays. -- Optional spa heat is available for $25/day. ***BOOKING RULES*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 years or older to book and must occupy the property during the entire stay. *** GUEST SERVICES *** Your Concierge & Service Fee includes your Guest Services Membership. Member Benefits -- Villa Concierge services - upon confirmation, before arrival, and during your stay. -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Proprietary Guest benefit & discount card -- 10% Advance Booking Discount for private charters -- Complimentary use of snorkel equipment -- Guest parcel receipt & hold for check-in -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Airport arrival Fast-Track VIP Process (fee charged by CAA) -- Arrange airport pick-up & rental vehicles (fee applies) -- Special event/dinner reservations At-Villa Benefits -- Welcome amenity basket -- Complimentary early check-in, if no check-out on the same day -- Day-after-arrival & mid-week guest services follow-up -- Complimentary use of Apple TVs, Bluetooth speakers, beverage coolers -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- $25,000 of Accidental Villa Damage Protection -- Complimentary pack-n-plays, booster seats, & baby gates -- Additional tandem kayaks available for discounted rental* *Signed waiver required. ***Getting Around*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Avis, or Marshalls. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. We try our best to work around Mother Nature.

Coconut Beach

Rum Point, KY
6 Bedrooms • 12 Guests

Oct 8 - 13
$1,029 night

***Property Overview*** Coconut Beach is an oceanfront family-friendly oasis located in the picturesque Rum Point community along Grand Cayman’s north coast. This large, one-story beach house spans 4,200 sq. ft. and can sleep 12 guests across 5 bedrooms in the main house, plus a detached 1 bed/1 bath studio suite above the garage. Perfect for vacationing grandparents or in-laws, the studio suite provides added privacy and is never rented out to unrelated guests during your stay. The focal point of the main house is the great room. Connecting both bedroom wings of the villa, and opening onto an enclosed sun porch, the great room provides sunny ocean views throughout the living, dining, and kitchen areas. With its airy, open concept design the great room includes a dining table with seating for 10, a TV den with two cozy couches, and a full kitchen with breakfast counter seating for 6. A separate kids’ table with chairs is provided for our tiny guests. *** Sleeping Arrangements *** (Sleeps 12 guests total) -- Bedroom 1: king bed, ocean views, ensuite with dual vanities and shower. -- Bedroom 2: queen bed, shares Jack & Jill bathroom equipped with a shower. -- Bedroom 3: 2 twin beds, shares Jack & Jill bathroom equipped with a shower; twin beds can be fitted into a king bed upon request. -- Bedroom 4: primary suite, king bed, ocean views, home office with desk + chair, ensuite with shower. -- Bedroom 5: 2 twin beds, ensuite half bath, uses full bathroom off the dining area equipped with a shower bath; twin beds can be fitted into a king bed upon request. -- Bedroom 6: detached apartment suite above the garage, queen bed, full kitchen, HD TV, full bathroom, air conditioning, washer & dryer. Outside, guests at Coconut Beach will enjoy the villa’s sandy, palm-shaded beach, great for long walks, or lazy afternoons with your toes in the sand. The villa’s wraparound patio leads to a new beach cabana with ample seating for sunset viewings. The pool deck is furnished with multiple loungers surrounding the villa’s freshwater plunge pool. An outdoor shower sits off the pool deck to rinse off after a long day of sun and surf. *** Coconut Beach’s Unique Features *** Outdoors: -- Located on a wide lot with lush landscaping, guests will feel they’ve been whisked away to their own enchanted garden by the sea. -- Newly expanded beach cabana with Adirondack chairs and patio seating. -- 2 beach hammocks for afternoon naps by the sea. -- Excellent snorkeling just steps from the backdoor! A healthy marine habitat awaits beneath the waves, we recommend pool shoes or fins for foot protection. -- Freshwater plunge pool with plenty of loungers around the pool deck. Indoors: -- Great beach house vibe with an open concept great room providing plenty of room for the entire family. -- Large flat-screen TV and comfortable sofas for a movie night after a day of sun and surf. -- Full kitchen with modern appliances and plenty of counter space. -- Enclosed sun porch with sofas and Adirondack chairs to enjoy the ocean views. ================= ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service added to all rates. -- Accidental Damage Protection added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire with your travel dates prior to booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 years or older to book and must occupy the property during the entire stay ***Property Manager Guest Services*** The 10% Guest Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Proprietary Guest benefit & discount card -- 10% advance booking discount for private charter -- Complimentary use of snorkel equipment -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors, guest services desk assistance At-Villa Benefits -- Day-after-arrival guest services follow-up -- Complimentary early check-in, if no check out on same day -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- Complimentary pack-n-plays, booster seats, & baby gates -- Kayaks available for discounted rental* *Signed waiver required. =================== ***Villa Cleaning & Sanitation*** All villas are cleaned and sanitized prior to each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival-- we try our best to work around Mother Nature.

Blue Vista Villa - Oceanfront 5 Bedroom Pool Home in North Side

Old Man Bay, North Side, KY
5 Bedrooms • 16 Guests

Oct 20 - 24
$1,183 night

Blue Vista Villa is a spacious 5 bedroom, 4.5 bath oceanfront retreat in the peaceful community of Old Man Bay on Grand Cayman’s North Side, with sweeping sea views, a private saltwater pool, and sleeping space for up to 16 guests. The property combines a 4 bedroom main villa and a separate oceanfront guesthouse, creating the ideal setup for families, multi generational groups, or friends who want both shared gathering spaces and extra privacy. 5 Bedrooms | 4.5 Bathrooms | Sleeps 16 LIVING AREA & ENTERTAINMENT • Large sunken living room with plush seating, 65" flat panel HDTV, DVD player, and Roku for streaming and movie nights. • Bright, open interior with ocean views from the main living areas, high ceilings, and Caribbean inspired décor for a breezy, relaxed feel. • Dedicated Games Room featuring classic Pac Man and Atari arcade machines plus Nintendo systems on the TV—always a hit with kids and grown ups alike. BEDROOMS & BATHROOMS Main Villa (4 Bedrooms – Sleeps up to 12) • Oceanfront Primary Suite: King size bed, en suite bathroom with walk in shower. • Second Oceanfront Bedroom: King size bed, shares a Jack and Jill bathroom with the garden view queen bedroom. • Garden View Bedroom: Queen size bed, shares Jack and Jill bathroom. • Large Bunk/Family Bedroom: Two queen size beds plus two twin single beds, with a private en suite bathroom featuring a shower/tub combo. Guesthouse (1 Bedroom + Bonus Bunks – Sleeps up to 4) • King Bedroom: King size bed with en suite bathroom and beautiful oceanfront view. • Bonus Sleeping: Twin bunk bed in the guesthouse living area, plus its own kitchen and dining space—perfect for friends, grandparents, or a family that wants some extra privacy. In total, Blue Vista can accommodate up to 16 guests in beds. FULLY EQUIPPED KITCHENS & DINING • Main villa gourmet kitchen with dual sinks, refrigerator/freezer, dishwasher, oven, ceramic cooktop, microwave, blender, and a Presto Cool Daddy deep fryer. • Oceanfront dining room seating 6, plus a separate breakfast area with teak seating for 6 more. • Guesthouse includes its own kitchen and dining area, ideal for early risers, separate family units, or added flexibility when traveling with a group. ESSENTIALS STARTER PACK INCLUDED Your stay includes a convenient starter supply of: • Shampoo, bath soap, and hand soap. • Laundry detergent and dishwashing liquid/tabs for the dishwasher. • Toilet paper, paper towels, blow dryer, iron, and ironing board. BEACH GEAR & PROPERTY AMENITIES • Private oceanfront saltwater pool with wide deck space for sunbathing and lounging. • Large screened in patio for shaded outdoor dining, card games, or relaxing with a book out of the sun. • Beachfront gazebo with hammocks and loungers for afternoon naps, sunset views, or quiet morning coffees by the sea. • Family friendly extras including beach toys, pool floats, board games, pack ’n play, and high chairs. • Direct access to the shoreline for beachcombing, plus excellent snorkeling on a nearby reef just a short walk down the beach. BEACH & WATER ACCESS Blue Vista Villa sits directly on the shoreline in Old Man Bay, with wide ocean views and a private saltwater pool overlooking the Caribbean Sea. The immediate beachfront in this area is a natural North Side shoreline, with a mix of sand and coral underfoot, making it great for relaxing by the water, beachcombing, and enjoying the view. Just a short walk down the beach, you’ll find a shallow sandy cove near the On The Bay condos that is ideal for wading and swimming on calmer days. Excellent coral reef snorkeling is also available roughly 100 yards along the shore, where the reef protects the water and offers plenty of marine life for confident swimmers and snorkelers. For comfort and safety, water shoes or fins are recommended anywhere you enter over rock or coral, and guests should always check daily sea conditions before heading into the sea. Guests who prefer classic, soft sand beach time can also explore North Side and East End public beach areas, as well as Rum Point and Kaibo, all a short drive away and offering easier walk in swimming and beach club style amenities. BEACH CONDITIONS Properties on the North Side and East End of Grand Cayman may occasionally see sargassum (seaweed) wash ashore, mostly between May and August. This is a natural, seasonal occurrence throughout the Caribbean, and conditions can vary day to day. Grand Cayman offers gorgeous beaches, great snorkeling, and plenty to enjoy island-wide, so we don’t anticipate it impacting your trip, just a heads-up in case you notice it during your visit. LOCATION & ACCESSIBILITY Blue Vista Villa is located in Old Man Bay on Grand Cayman’s quiet North Side, about a 30–40 minute drive from Owen Roberts International Airport in George Town under typical traffic conditions. The home sits between the Rum Point/Kaibo area and East End, putting you in a convenient spot for exploring both the laid back North Side and the dive friendly East End coastline. Old Man Bay Beach is just steps from the villa, while a shallow cove suitable for wading and swimming lies a short walk away down the shoreline. Popular nearby spots such as the Mastic Trail, Barefoot Beach, Queen Elizabeth II Botanical Garden, and the East End resort area are all within an easy drive. A rental car is strongly recommended here, as public transportation is limited and driving is the easiest way to reach supermarkets, restaurants, Rum Point, Kaibo, and Seven Mile Beach DINING & NEARBY ACTIVITIES • Over the Edge Café – About a 5–10 minute drive east along North Side Road for casual local dining with classic waterfront views. • Rum Point Club & Restaurant – Usually 15–20 minutes away for oceanfront dining, beach bar favorites, hammocks, and a relaxed beach club vibe. • Red Sail Sports at Rum Point – Also around 15–20 minutes by car for Stingray City trips, snorkeling, diving, paddleboarding, and kayak rentals. • Kaibo Beach Bar & Grill – Roughly 15–20 minutes’ drive for casual beachfront lunches, wood fired pizzas, and sunset cocktails. • Upstairs at Kaibo – Upscale fine dining above Kaibo Beach Bar, also about 15–20 minutes away. • Kaibo coffee spot – In the same Kaibo complex, typically 15–20 minutes away, great for coffee, pastries, and easy breakfast starts. • La Casita (East End) – Around a 20–25 minute drive toward East End for Mexican fare in a relaxed setting. • Tukka East & Eagle Ray’s – Approximately 20–25 minutes away for East End seafood, lionfish dishes, and island style menus overlooking the reef. • Morritt’s / East End resort area – Also about 20–25 minutes by car, with additional restaurants, beach bars, and oceanfront dining options. NEARBY ATTRACTIONS & HIGHLIGHTS • Starfish Point – Typically 15–20 minutes by car via the Kaibo/Rum Point area, popular for shallow water and starfish viewing. • Stingray City sandbar – Reached by boat tours departing from Kaibo or Rum Point. • Cayman Crystal Caves – About a 10–15 minute drive inland from the North Side/Old Man Bay area. • Queen Elizabeth II Botanical Garden – Generally 15–20 minutes away via Frank Sound Road, with nature trails, iguanas, and tropical gardens. GROCERIES, SUNDAY CLOSURES & PRACTICAL DETAILS Nearby grocery options such as Foster’s Express and Chisholm’s Grocery are about 15 to 20 minutes away by car. Larger supermarkets are also convenient stops on the drive from the airport. Supermarkets are closed on Sundays in Cayman, though most restaurants and gas stations remain open, and some gas stations sell liquor on Sundays. Grocery items can also be pre-ordered and delivered before arrival. Chisholm’s Market is on the Northside, and is open 7 days a week, and is well stocked with food, supplies, beer, wine & liquor. 15 minutes from the condo. TRANSPORTATION • A rental car is highly recommended for this area so guests can easily explore Grand Cayman at their own pace. • Many guests book directly with trusted local providers such as Marshall’s Rent-A-Car, Andy’s Rent-A-Car, or compare options through Kayak. • Public transportation is a short walk away, having a car offers the greatest convenience and flexibility. ACCESSIBILITY & PARKING Accessibility: Single-level home with minimal steps Parking: Ample on-site parking is available for guest use PROMOTIONS Automatic discounts may apply based on travel dates, including seasonal Stay 7, Pay 6 offers from May 1 to November 1, along with last-minute deals, early booking savings, and extended-stay discounts. Eligible offers are applied automatically, cannot be combined with other promotions or Repeat Guest benefits, and may be subject to blackout dates from December 17 to January 3. CHECK IN & CHECK OUT After booking, you’ll receive detailed arrival information by email, and your unique door code before arrival. Check in is any time after 4:00 PM with keyless entry; early check in may be possible depending on cleaning schedules and can be confirmed with the property manager closer to arrival. Check out is self service at 11:00 AM, with clear instructions provided; late check out is only available if pre arranged, as time is needed to prepare for incoming guests. TRAVEL INSURANCE Travel insurance is recommended, especially during hurricane season from August through October, to help protect against trip interruptions and weather-related disruptions. Stay 7 Pay 6 Blue Vista Villa

Ocean Kai

Rum Point, KY
6 Bedrooms • 12 Guests

Oct 10 - 15
$1,489 night

***Property Overview*** Ocean Kai is built on the oceanfront along a sandy ridge in Cayman Kai. Spanning over 5,500 square feet of vaulted living space and an open design, Ocean Kai sleeps 12 guests across six bedroom suites. Upon entering the great room there is an immediate "wow factor" as your eyes take in the ocean views through a wall of glass doors and windows looking out over the pool deck. The open living area has a cathedral ceiling accentuating the home’s size and grandeur. A mezzanine loft with a glass railing serves as a media room and has an oceanfront windowed dormer with outstanding ocean views. A full-width, oceanfront shaded veranda overlooks a 38-foot private pool with steps leading down to your own sandy beach. The veranda is furnished with plush sectional seating and an outdoor dining area. *** Sleeping Arrangements *** (Sleeps 12 guests total) -- Bedroom #1: primary suite, oceanfront, king bed, television, walk-out access to the pool deck, ensuite with dual vanity, soaking tub, and separate shower. -- Bedroom #2: oceanfront, king bed, television, walk-out access to the pool deck, ensuite with dual vanity, soaking tub, and separate shower. -- Bedroom #3: oceanfront, king bed, television, walk-out access to the pool deck, ensuite with dual vanity, soaking tub, and separate shower. -- Bedroom #4: queen bed, television, ensuite with shower bath. -- Bedroom #5: queen-over-twin bunk beds, ensuite with shower. -- Bedroom #6: queen bed, television, ensuite with dual vanity, soaking tub, and separate shower. Ocean Kai’s kitchen is a vacationing chef’s paradise. Featuring marble countertops, all-white cabinets, and high-end appliances, guests can whip up a home-cooked meal or hire a private chef for a night of in-villa dining. Guests can choose to eat in the formal dining room or step out onto the veranda for a night of al-fresco dining. A propane grill is located near the pool deck for island cookouts. Notes: Additional tandem kayaks are available for discounted rental. Signed waiver is required. ===== ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 12.90% Villa Concierge & Service Fee is added to all rates. -- A Departure Cleaning Fee is added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire with your travel dates prior to booking. -- Shorter stays may be available but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 years or older to book and must occupy the property during the entire stay. -- Check-in is at 3:00 pm. -- Check-out is at 10:00 am. ***Property Manager Services*** The Villa Concierge & Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Proprietary Guest benefit & discount card -- 10% advance booking discount for private charter -- Complimentary use of snorkel equipment -- Guest parcel receipt & hold for check-in -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors, guest services desk assistance -- Airport arrival Fast-Track VIP Process (fee charged by CAA) -- Special event/dinner reservations At-Villa Benefits -- Welcome amenity basket -- Complimentary early check-in, if no check-out on the same day -- Day-after-arrival guest services follow-up -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- $2,500 of Accidental Villa Damage Protection -- Complimentary pack-n-plays, booster seats, & baby gates -- Kayaks and stand-up paddleboards (SUPs) available for discounted rental* *Signed waiver required. =================== ***Villa Cleaning & Sanitation*** All villas are cleaned and sanitized prior to each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. The beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. We try our best to work around Mother Nature.

Timmy’s Place

Rum Point, KY
3 Bedrooms • 8 Guests

Oct 8 - 13
$477 night

***Property Overview*** Welcome to Timmy’s Place, a brand-new oceanfront villa with spectacular views and a sandy backyard beachfront in peaceful Rum Point. This spacious 3-bedroom, 3.5-bathroom home is perfect for families and traveling groups seeking a relaxing island retreat within driving distance to beachfront dining and watersport options in neighboring Cayman Kai. The home’s upper level offers spectacular elevated views of the Caribbean Sea from the living areas to the expansive wraparound deck, perfect for enjoying your morning coffee with inspiring sunrise views. The deck and a lower-level patio are furnished with outdoor dining tables for alfresco meals by the sea. A propane grill sits on the oceanside of the deck, perfect for surf-and-turf cookouts. Inside, the upper level’s open-concept design includes a full kitchen with modern appliances plus a cozy living area furnished with a comfy sectional sofa and wall-mounted SmartTV. All three bedrooms sit on the upper level and feature walkout access to either the wraparound deck or a shared balcony. ***Sleeping Arrangements*** (Licensed to sleep 8 guests, 6 adults max.) -- Bedroom 1: primary suite, upper level, king bed, SmartTV, walkout access to the wraparound deck, ensuite with shower. -- Bedroom 2: upper level, queen bed, SmartTV, walkout access to a shared balcony, shares a Jack & Jill bathroom equipped with a shower. -- Bedroom 3: upper level, queen bed, SmartTV, walkout access to a shared balcony, shares a Jack & Jill bathroom equipped with a shower. -- Additional Sleeping: sleeper sofa in the lower-level den for two children only. On the ground level, a second den has been converted into a hybrid media room and recreation space just beyond the foyer. Guests will find a convertible air hockey & ping pong table, plus a dart board for friendly match play. The den also features a sleeper sofa, a SmartTV for streaming, and walkout access to the lower-level patio. For those who prefer to stay out of the sun, the lower-level patio is a shady retreat with a hammock for siestas by the sea. An outdoor shower also adds convenience to wash off after a day of backyard beach fun. The villa is surrounded by natural beauty, including a large area to the left with sandy pathways, beach chairs, and solar lighting, creating private hideaways for quiet moments or daytime adventures for kids. A public, beachfront gazebo and swing set sit to the right of the villa for everyone to enjoy. Need to work remotely while staying at Timmy’s Place? The villa comes equipped with a dedicated workspace at the end of the top-level hallway for your work needs. Guests can enjoy incredible snorkeling and kayaking (pictured kayaks available for rent) right from the beach with barefoot entry into the crystal-clear Caribbean waters. Plus, Timmy’s Place boasts an exceptional location, less than half a mile from the watersports and beachfront dining at the Rum Point Club and the Kaibo, making it the perfect blend of comfort, adventure, and island charm. *Notes: Bike rentals plus single/tandem kayaks and Seaview boards are available at discounted rates. A signed waiver is required. ================ ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service Fee added to all rates. -- Accidental Damage Protection added to all rates. -- A Departure Cleaning Fee is added for all stays. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays are welcome but subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 or older to book and must occupy the property during the entire stay. -- Check-in is 3:00 pm; Check-out is 10:00 am. ***Property Manager Guest Services*** The 10% Guest Service Fee includes the following member benefits: -- Centralized on-island Guest Services & Welcome Center -- Complimentary snorkel equipment for use during your stay -- Complimentary pack-n-plays, booster seats, & baby gates -- 10% advance booking discount towards a private charter -- Guest 10% discount card with preferred vendors (restaurants, watersports, charters, etc.) -- Unlimited use of our Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Referral to preferred vendors, guest services desk assistance -- Complimentary early check-in, if no check-out on the same day -- Tandem kayaks and paddleboards are available for discounted rental* *Signed waiver required. ***Nearby Points of Interest*** -- 1.0 mile west to the Rum Point Club and Bioluminescent Bay -- 2.4 miles to the Kaibo Beach Bar & Grill & Starfish Point -- 3.5 miles to the nearest grocery store, Chisholm’s Grocery -- 5.5 miles east to Over the Edge restaurant and the Cayman Crystal Caves -- 7.9 miles from our Welcome Center -- 11.6 miles east to the nearest supermarket, Foster’s Express, and the resorts at Morritts and Wyndham Reef Resort -- 13.6 miles to Tukka East Restaurant & Bar and the Cayman Parrot Sanctuary -- 14.7 miles to La Casita Taco & Tequilla Bar -- 25.0 miles (48-minute drive) from Owen Roberts Int’l Airport (GCM) ***Getting Around*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Marshalls, or Hertz. ***Beach Notes*** All beaches in Grand Cayman are technically public, since the Crown extends to the high-water mark. Be advised that the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked before your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions, which may include a partial refund or relocation. We try our best to work around Mother Nature.

S’Kai Fall

Rum Point, KY
3 Bedrooms • 7 Guests

Oct 23 - 28
$719 night

***Property Overview*** Tucked away on an oversized lot in tranquil Cayman Kai is where you’ll find our newest slice of paradise. Welcome to S’kai Fall! This modern 3-bedroom, 3-bath beach house has undergone a complete makeover, both inside and out. Plus, the villa’s recently upgraded fiber internet connection provides reliable speeds and increased bandwidth for work-from-home professionals. A new freshwater pool with submerged ledge loungers has been installed steps off the wide, private beachfront, perfect for sunbathers. The expansive pool deck overlooks the waterfront and comes complete with outdoor sofa seating and reclining chaise lounges. Facing due west, the stunning water views continue into the evening with amazing sunset vistas perfect for island happy hours. A new palm-fringed, circular driveway welcomes you to your sunny, island abode. Upon entering the villa, your eyes will be drawn through the wall of sliding glass doors to the water views beyond the screened veranda and pool deck. The spacious, open-concept great room links the living area, dining area, and kitchen with breakfast counter seating. Sliding glass doors provide seamless indoor/outdoor living, allowing you to open the great room to the home’s full-width, screened veranda. Restoration Hardware furniture and decor have been used throughout the villa, giving it an elegant and contemporary feel. S’kai Fall has 2 bedrooms upstairs, each with en-suite baths, water views, and walk-out access to a shared screened veranda--a great perch to enjoy your morning coffee while checking emails. The third bedroom on the lower level shares a hall bathroom and is ideal for younger guests. ***Bed and Bathroom Layout*** (Sleeps 7 Guests or 6 Adults Max) -- East Suite - upper-level, king bed, waterfront views, wall-mounted cable TV, walk-out access to shared screened balcony, ensuite bath with double vanity, shower, and bathtub. -- West Suite - upper-level, king bed, waterfront views, wall-mounted cable TV, walk-out access to shared screened balcony, ensuite bath with tub shower combo. -- Twin Bedroom - lower level, 2 twin beds with extra single trundle bed, dresser, and wall-mounted SmartTV; shares an adjacent hall bath with shower. The Cayman Kai cove is home to the famous Bioluminescent Bay. Kayaks and paddleboards are available for rent with free delivery. Guests can launch off the beach on a moonless night to explore the glowing waters of Bio Bay. The cove water is shallow with a muddy bottom. Recreational swimming and snorkeling are best enjoyed at the Rum Point Club, just a 5-minute walk north. There you will also find jet ski rentals, excursions to Stingray City, plus a restaurant, an alfresco bar, and a gift shop. Combined with its central location on the Cayman Kai peninsula, and walkable to water activities, family-friendly restaurants, and laid-back beach bars, this island getaway is sure to become a guest favorite. Come experience easy-island living in beautiful Cayman Kai! NOTES: Bicycles, kayaks, and paddleboards are available for discounted rental. Signed waiver required. Paddles included. ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service added to all rates. -- Accidental Damage Protection added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays may be available but are subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 years or older to book and must occupy the property during the entire stay. ***Grand Cayman Villas & Condo Guest Benefits*** The 10% Guest Service Fee includes your Guest Services Membership. Member Benefits -- 10% advance booking discount for private snorkel charters. -- Complimentary use of snorkel equipment during your stay. -- Guest benefit & discount card for up to 10% discounts at local businesses. -- Centralized on-island Guest Services & Welcome Center. -- Jacques Scott Wine & Spirits pre-order & hold for check-in. -- Referral to preferred vendors, guest services desk assistance. -- Unlimited use of Private Fitness Center (18+ yrs). -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies. At-Villa Benefits -- Complimentary pack-n-plays, booster seats, & baby gates. -- Pre-stocking of groceries & beverages (delivery fee applies). -- Complimentary early check-in, if no check-out on the same day. -- Day-after arrival guest services follow-up. -- Gilchrist & Soames bath products provided. -- Arrange chefs, cooks, babysitting & family photography. -- Stand-up paddleboards (SUPs) available for discounted rental.* *Signed waiver required. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival.

Hilltime

Rum Point, KY
5 Bedrooms • 12 Guests

Oct 8 - 13
$978 night

***Property Overview*** Welcome to Hilltime, a spacious single-story beachfront villa located in beautiful Rum Point. Featuring multiple bedroom terraces, a private pool, and backyard snorkeling, Hilltime is a fabulous destination along the island’s North Side. Hilltime’s family room has been reconfigured by separating the dining and living areas to free up space for everyone in your group to spread out. The living area has been reshuffled with sofa seating and a wall-mounted television opposite the kitchen area. A new dining table sits against the windows providing beachfront views with every meal. Vaulted ceilings and tall windows allow natural light and sweeping views to fill the home. The new layout makes the best use of the space while accentuating the stunning ocean views throughout. In addition to the family room, a double bunk room has been added to sleep 4 children or 2 adults. The bunk room comes furnished with a SmartTV and plush round poufs for comfy seating. The bunk room shares an adjacent hall bathroom with the East Bedroom. Other upgrades include a Sonos Home Sound System. Set the vibe and let your favorite songs fill the home. A portable Sonos Move is located in the kitchen. Just grab it off its base and take your tunes to the beach or pool deck! The villa’s 5 bedrooms are divided by the family room with 2 on the west wing and 3 on the east wing. ***Sleeping Arrangements*** (Sleeps 10 adults, 12 guests max.) -- West Primary Suite: king bed, ocean views, television, blackout blinds, walk-out oceanfront terrace, ensuite with double vanity, makeup counter, large shower with walk-out access to the pool deck. -- West Suite: king bed, ocean views, large closet, blackout blinds, walk-out oceanfront terrace, and ensuite with shower. -- East Suite: king bed, ocean views, large closet, blackout blinds, walk-out oceanfront terrace, and ensuite with shower. -- East Bedroom: king bed, ocean views, large closet, blackout blinds, walk-out oceanfront terrace, shares adjacent hall bath equipped with shower bath. -- East Bunk Room: 2 sets of twin bunks, SmartTV, blackout blinds, shares adjacent hall bath equipped with shower bath. The home’s freshwater pool sits on the land-side of the villa protecting guests from trade winds in the winter and absorbing most of the sun’s rays. Sail shades and all-new sun loungers circle the pool deck. The pool deck also includes a cabana for shady relief from the island sun. For the grill master in your group, a new Weber propane grill is provided for island cookouts. Inside, the gourmet kitchen comes equipped with everything you need to prepare a home-cooked meal. Modern appliances including dishware, utensils, glassware, and cookware are all provided. Hire a private chef for a night of in-villa dining or start your morning with a champagne brunch! The beach behind the villa is wide and sandy with superb snorkeling inside the reef-protected shallows. Children, and the young at heart, will love the custom wood swing set installed along the beach. The property sits on a deep estate of over an acre with heavily landscaped grounds. Plenty of off-street parking is available with room to turn around in the driveway. =============== ***Nearby Attractions*** -- 1 mile to the Rum Point Club & the island’s Bioluminescent Bay -- 2.5 miles to beachfront dining at the Kaibo, ferry service to Camana Bay/Seven Mile Beach, and a laid-back beach at Starfish Point -- 3.5 miles to the nearest general store, Chisholm’s Grocery -- 5.3 miles east to Over the Edge restaurant -- 5.8 miles to Cayman Crystal Caves -- 8 miles from our Silver Thatch Welcome Center -- 11.6 miles to the nearest supermarket, Foster’s Express -- 25 miles (47 min drive) from Owen Roberts Airport (GCM) ***Getting Around*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Marshalls, or Hertz. ====== ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service added to all rates. -- Accidental Damage Protection added to all rates. -- A Cleaning Fee is added to all rates. -- Additional tandem kayaks are available for discounted rental. A signed waiver is required. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire with your travel dates prior to booking. -- Shorter stays may be accepted but subject to a higher cleaning fee. -- Must be 25 years or older to book and must occupy the property during the entire stay ***Property Manager Guest Services*** The 10% Guest Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island guest services & welcome center -- Unlimited Use of Private Fitness Center (18+ yrs.) -- Business Center with computers, printer/scanner, and FedEx/DHL supplies -- Proprietary Guest benefit & discount card -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors and reservations assistance -- 10% advance booking discount for private charter -- Complimentary snorkel gear, pack-n-plays, booster seats, and baby gates for checkout At-Villa Benefits -- Complimentary early check-in (if no check-out on the same day) -- Day-after-arrival guest services follow-up -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Coordinate private chefs, cooks, babysitting & family photographer -- Kayaks available for discounted rental* *Signed waiver required. ================ ***Villa Cleaning & Sanitation*** All villas are cleaned and sanitized before each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. We try our best to work around Mother Nature.

Babylon Reef

North Side, KY
3 Bedrooms • 6 Guests

Oct 10 - 15
$604 night

***Property Overview*** Welcome to Babylon Reef, a freshly renovated oceanfront villa, complete with a sundeck and private pool, situated directly on one of the best shallow snorkeling sites on the entire island. Protected by a coral reef, there are rarely any currents or waves to contend with so children can play in the shallows all day. The ocean views are stunning the moment you walk through the front door. Natural light and scenic ocean views flood the entire living area through the sunroom’s retractable glass doors, which can be opened to allow a breeze to flow through on days when air conditioning is unnecessary. Cute Caribbean architecture and a modern, open-concept design lend a great island feel throughout. A full kitchen, complete with modern appliances, overlooks the dining area with seating for 6. An outdoor dining table on the pool deck, under tall palm trees, is also available. All cookware, glassware, cutlery, and flatware are provided. Sleeping Arrangements (Sleeps 6 guests total) -- Bedroom 1: primary suite, lower-level, king bed, ocean views, walk-out access to the sunroom, ensuite with shower. -- Bedroom 2: upper-level, king bed, ocean views, shares hall bathroom equipped with a shower bath. -- Bedroom 3: upper-level, two twin beds, ocean views, shares hall bathroom equipped with a shower bath; beds can be fitted into a king bed upon request. Babylon Reef’s private, well-landscaped lot includes a white picket fence, soft zoysia grass lawns, and a large sandy backyard around the pool. The owner provides a cornhole set on the beach, complete with boards and bean bags, plus 2 tandem kayaks and 1 child-size kayak for exploring, beach hammocks for relaxing, and an outdoor shower with hot and cold running water. With an empty lot on each side, Babylon Reef is a private and secluded retreat. The beach can be both sandy and pebbly depending on the time of year, therefore, we advise guests to bring pool shoes to avoid foot injuries. Two large resorts with water sports, manicured sandy beaches, and oceanfront bars and restaurants are just a short 10-minute drive east. *Note: Adult and kid bicycles, plus tandem and single kayaks, are available for discounted rental; a signed waiver is required. ================================ ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service Fee added to all rates. -- Accidental Damage Protection added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays may be available but are subject to a higher cleaning fee. Please inquire in order to book. -- Must be 25 or older to book and must occupy the property during the entire stay. ***Property Manager Guest Services*** The following perks are provided throughout your stay: Member Benefits -- Complimentary use of snorkel equipment -- Complimentary pack-n-plays, booster seats, & baby gates -- Centralized on-island Welcome Center with free access to a private gym -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Guest Discount Card for 10% savings at restaurants and businesses -- 10% advance booking discount towards a private charter -- Referral to preferred vendors, guest services desk assistance -- Complimentary early check-in, if no check out on the same day -- Additional kayaks available for discounted rental* *Signed waiver required. =================== ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions which may include a partial refund or relocation. We try our best to work around mother nature.

White Dahlia

Rum Point, KY
4 Bedrooms • 10 Guests

Oct 8 - 13
$1,259 night

***Property Overview*** Welcome to White Dahlia. This multi-windowed, open-concept floor plan offers up to 10 guests an opportunity to spend their vacation free of clutter with smart home technology and luxurious amenities. Soaring ceilings, walls of glass, and a quiet cove with a private dock create a serene enclave for your family and friends to enjoy. With a white sandy beach diagonally across the street, this contemporary villa provides a welcome escape after a day in the sun at Rum Point or out on the water. **Bedroom Configuration** -- Bedroom 1: primary suite, California king bed, water views, walk-out access to the pool deck, television, walk-in closet, ensuite with dual vanity, soaking tub, and separate shower. -- Bedroom 2: king bed, water views, walk-out access to the pool deck, television, ensuite with dual vanity, and shower. -- Bedroom 3: king bed, water views, walk-out access to the pool deck, television, ensuite with dual vanity, and shower. -- Bedroom 4: two twin beds, island views, ensuite with shower; twin beds can be fitted as a king bed upon request. -- Den/Office: queen sleeper sofa, island views, television, desk + chair, closet, ensuite with shower. **Key Features** -- Large great room with vaulted ceilings and walk-out access to the pool deck, outdoor dining area, and quiet cove behind the villa. -- Large private pool with spa and toddler splash zone; SPA HEAT INCLUDED -- Barefoot beach access diagonally across the street. -- Sleek contemporary decor throughout with central air conditioning, and high-speed fiber wifi for streaming and remote working professionals. -- HD TVs in living areas and bedrooms, along with USB-charging night lamps. -- Private dock for charter boat pick-up. -- Large ceramic dining table with seating for 10. -- Wheelchair entry ramp along the side door; handicap-accessible shower in the twin-bedroom suite. -- Gourmet kitchen with induction cooktop, Sub-Zero wine fridge, two dishwashers, additional Sub-Zero refrigerated drawers, and freezer drawer with ice machine. -- Additional freezer in the utility room. -- Home Security System available upon request. -- Soft evening LED illumination throughout. -- Tandem kayaks and stand-up paddleboards (SUPs) are available for discounted rental. A signed waiver is required. ======= ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 12.90% Villa Concierge & Service Fee is added to all rates. -- A Departure Cleaning Fee is added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays are welcome but subject to a higher cleaning fee. Please inquire to book. -- Must be 25 or older to book and must occupy the property during the entire stay. -- Check-in is at 3:00 pm. -- Check-out is at 10:00 am. ***Property Manager Guest Services*** The Villa Concierge & Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Proprietary Guest benefit & discount card -- 10% advance booking discount for private charter -- Complimentary use of snorkel equipment -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors, guest services desk assistance At-Villa Benefits -- Day-after-arrival guest services follow-up -- Complimentary early check-in, if no check-out on the same day -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- $1,500 of Accidental Villa Damage Protection -- Complimentary pack-n-plays, booster seats, & baby gates -- Kayaks and stand-up paddleboards (SUPs) available for discounted rental* *Signed waiver required. ================= ***Nearby Points of Interest*** -- Located on the island’s Bioluminescent Bay -- Short walk to the Rum Point Club and Rum Point Resort. -- Short drive to Starfish Point and dining at The Kaibo. -- 9.1 miles from our Guest Welcome Center. -- 26.4 miles (50 min drive) from Owen Roberts Airport (GCM) ***Getting Around*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Avis, Marshalls, or Hertz. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked before your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions, which may include a partial refund or relocation. We try our best to work around Mother Nature.

Vacation Rentals in North Side by Amenities & Features

Get to Know North Side

North Side, located on the picturesque Grand Cayman Island, offers a serene and intimate escape from the more bustling tourist spots like George Town and Seven Mile Beach. This tranquil area is known for its stunning natural beauty, friendly community, and a slower pace of life that allows visitors to unwind and soak in the Caribbean charm. One of the main attractions in North Side is the world-renowned Rum Point, where travelers can relax on white sandy beaches with a famous mudslide in hand, a cocktail that has become synonymous with the area. The shallow and clear waters here are perfect for swimming and snorkeling, offering a glimpse into the vibrant underwater world of colorful coral and diverse marine life. For those interested in the unique natural wonders of the Cayman Islands, a visit to the enchanting Crystal Caves is a must. These ancient geological formations provide an otherworldly experience as you explore the stalactite and stalagmite crystal structures within the subterranean caverns. Adventure seekers will find plenty to do in North Side as well. Kayaking through the calm waters allows for an up-close encounter with the island's lush mangroves and wildlife. For a truly magical experience, nighttime excursions to Bio Bay reveal the mesmerizing phenomenon of bioluminescence, where microscopic organisms light up the water with a blue glow. Birdwatchers and nature enthusiasts will appreciate the peaceful Mastic Trail, a 200-year-old path that winds through a native mangrove swamp and a dry subtropical forest. This area is home to a variety of endemic species and offers a chance to connect with the island's natural environment. Dining in North Side reflects the island's cultural melting pot, with local seafood restaurants serving up fresh catch alongside international cuisine. The laid-back atmosphere of the district's eateries allows for leisurely meals with stunning ocean views. Accommodations in North Side range from cozy beachfront cottages to luxurious villas, catering to different preferences and ensuring a comfortable stay. The area's seclusion makes it ideal for those seeking privacy and a chance to disconnect from the outside world. In essence, North Side is a destination that offers a blend of relaxation, natural beauty, and adventure. It's a place where travelers can experience the authentic spirit of the Cayman Islands, away from the crowds, and create memories that will last a lifetime.
North Side, located on the picturesque Grand Cayman in the Cayman Islands, offers a tropical marine climate that is warm and inviting year-round. The weather is one of the key attractions for visitors seeking a sun-soaked Caribbean getaway. The temperature in North Side is fairly consistent, with average highs ranging from the mid-80s to low 90s Fahrenheit (around 29-34°C) throughout the year. The warmest months tend to be from May to October, which coincides with the rainy season. During this time, humidity is higher, and the heat can feel more intense, but the sea breezes typically provide a refreshing respite. Rainfall is more prevalent in the summer and early fall, with September and October often being the wettest months. However, showers are usually short-lived and can provide a welcome break from the heat. The islands average about 50 inches (1270 mm) of rain annually, with the majority falling during this period. The winter months, from November to April, are considered the dry season and are characterized by slightly cooler temperatures, with average highs in the low to mid-80s Fahrenheit (around 27-29°C). This is the peak tourist season, as the weather is particularly pleasant with lower humidity and less rainfall. Nights can be cooler, so a light sweater might be needed, especially if you're near the water. Hurricane season spans from June to November, with the highest risk typically from August to October. While direct hits are rare, it's important to be aware of this if you're planning a trip during these months. The most popular weather conditions are found during the dry season, particularly from mid-December to April, when the climate is especially pleasant. This is the ideal time for beach activities, snorkeling, and diving, as the sea is calm and visibility is at its best. The North Side's famous attractions, like the Crystal Caves and the tranquil beaches, are most enjoyable when the sun is shining and the skies are clear. Whether you're looking to relax on the beach, explore the underwater world, or simply soak up the Caribbean sun, North Side's climate offers a warm welcome almost any time of the year. However, for the best balance of good weather and outdoor activities, planning your visit during the dry season is recommended.
North Side, located on the picturesque Grand Cayman in the Cayman Islands, offers a serene and culturally rich experience for travelers who revel in the arts, history, and local customs. While it may not boast the bustling city vibe of larger destinations, its charm lies in the authentic cultural experiences and the tranquil beauty of its natural surroundings. Begin your cultural journey at the Mission House in Bodden Town, a short drive from North Side. This historic site provides a glimpse into the lives of early Caymanian settlers and serves as a testament to the island's missionary and educational history. The lovingly restored house and its artifacts offer a narrative of domestic life in the 18th and 19th centuries. Art enthusiasts will find solace in the local galleries that dot the island, showcasing the work of Caymanian artists. The National Gallery of the Cayman Islands, although located in George Town, is worth the trip for its impressive collection of contemporary and historical artwork that reflects the rich cultural heritage and natural environment of the Cayman Islands. Live music can be enjoyed at various venues and events throughout the year. The Cayman Islands are known for their love of music, with genres ranging from calypso and reggae to jazz and folk. Keep an eye out for local beach bars and restaurants in North Side that often host live bands, providing a laid-back atmosphere to enjoy the island rhythms. For a deep dive into local customs, the Cayman Islands National Museum in George Town presents a wealth of information about the island's natural and cultural history. Closer to North Side, the Queen Elizabeth II Botanic Park is a living museum where visitors can stroll through traditional Caymanian gardens and learn about the indigenous flora and fauna. Cultural events are a highlight of the Caymanian social calendar, with the annual Pirates Week Festival being a prime example. This island-wide celebration features parades, music, street dances, and reenactments of pirate invasions, offering a unique and lively way to engage with local customs and history. Lastly, no visit to North Side would be complete without experiencing the local culinary delights. Traditional Caymanian cuisine, with its emphasis on fresh seafood and Caribbean spices, can be savored at local eateries. Enjoy a seaside meal while soaking in the views of the crystal-clear waters and the soothing Caribbean breeze. North Side, with its tranquil beaches, rich cultural offerings, and warm local hospitality, provides a peaceful yet engaging backdrop for travelers seeking a cultural immersion in the arts, history, and customs of the Cayman Islands.
North Side, located on the picturesque Grand Cayman in the Cayman Islands, is a tropical paradise that offers a plethora of activities for families traveling with children. This serene and less crowded region of the island is perfect for those looking to enjoy a more relaxed pace while still having access to engaging and fun experiences for the little ones. One of the main attractions in North Side is the Cayman Turtle Centre, an education and research facility where kids can learn about and interact with sea turtles. The center offers a unique opportunity to get up close with these majestic creatures, and children can even participate in the turtle release program during certain times of the year. For a day at the beach, Rum Point is a family favorite. With its shallow, clear waters and soft white sand, it's an ideal spot for children to swim and play safely. The area is equipped with hammocks, picnic tables, and beach volleyball courts, ensuring a comfortable and entertaining day for the entire family. Adventure-seeking families can visit the Crystal Caves, one of the island's newest natural attractions. Guided tours take you through the stunning underground cave system, where children can marvel at the stalactite and stalagmite formations and learn about the geological history of the Cayman Islands. The Queen Elizabeth II Botanic Park is another must-see, especially for families who appreciate nature. Children can explore the colorful gardens, spot the endangered Blue Iguana in its natural habitat, and enjoy the park's playground. The Heritage Garden within the park gives a glimpse into traditional Caymanian life, which can be both educational and fascinating for young visitors. For a more immersive cultural experience, take the family to the East End Light House Park, where kids can see one of the island's iconic lighthouses and enjoy the panoramic views of the Caribbean Sea. The park surrounding the lighthouse offers a peaceful setting for a family picnic. Lastly, no visit to North Side would be complete without a snorkeling trip to see the vibrant coral reefs and marine life that the Cayman Islands are famous for. Many local operators offer family-friendly snorkeling tours that cater to all levels of experience, ensuring that even the youngest of swimmers can enjoy the underwater wonders safely. In North Side, Cayman Islands, families can enjoy a blend of educational experiences, outdoor adventures, and relaxing beach days, all set against the backdrop of the island's stunning natural beauty.
North Side, located on the picturesque Grand Cayman in the Cayman Islands, is a serene and naturally beautiful destination that offers a wealth of outdoor activities and natural wonders for those who love to immerse themselves in nature. One of the main attractions in North Side is the Mastic Trail, a 2.3-mile path that takes you through a native mangrove swamp and a 2 million-year-old woodland area. This trail is perfect for bird watchers and nature enthusiasts, as it is home to a variety of bird species and indigenous plants. The hike offers a glimpse into the island's natural history and is a great way to experience the island's diverse ecosystems. For those who are drawn to the water, North Side provides ample opportunities for snorkeling and diving in crystal-clear waters. The Coral Garden is a popular snorkeling spot where you can swim alongside vibrant coral reefs and a multitude of tropical fish. Diving enthusiasts can explore the nearby barrier reef or venture to famous dive sites such as Babylon, known for its stunning coral walls and marine life. Kayaking and paddleboarding are also popular activities in North Side, with calm waters that are ideal for paddlers of all skill levels. Exploring the coastline by kayak or paddleboard allows you to discover secluded coves and beaches that are not easily accessible by land. For a truly unique experience, visit the bioluminescent bay near North Side at night. Here, you can take a guided kayak tour to witness the magical glow of bioluminescent plankton that light up the water with every stroke of your paddle. Beach lovers will find solace on the quiet and unspoiled sands of North Side's beaches, such as Rum Point and Starfish Point. These beaches offer a peaceful retreat from the more crowded tourist spots, and Starfish Point is particularly known for its clear shallow waters where starfish can be seen dotting the seabed. Lastly, the Queen Elizabeth II Botanic Park is a short drive from North Side and is a splendid place to enjoy the island's flora and fauna. The park features a woodland trail, colorful gardens, and the Blue Iguana Habitat, where you can see the endangered Grand Cayman blue iguana in its natural environment. North Side, Cayman Islands, is a destination that offers a tranquil escape into nature's embrace, with a variety of outdoor activities and natural wonders that cater to the desires of any nature enthusiast.
North Side, located on the picturesque Grand Cayman in the Cayman Islands, offers a tranquil escape with its stunning beaches and laid-back atmosphere. While it may not have the extensive public transportation systems of larger cities, there are still several convenient options for travelers to arrive, depart, and explore this Caribbean gem. Most visitors arrive at Owen Roberts International Airport in George Town, which is the main gateway to the Cayman Islands. From the airport, the most common way to reach North Side is by renting a car or taking a taxi. Car rentals are widely available at the airport, and driving allows for the flexibility to explore the island at your own pace. The drive to North Side is scenic and straightforward, taking you through the heart of Grand Cayman. Taxis are also a reliable option, though they can be more expensive than renting a car, especially if you plan to make multiple trips or explore various parts of the island. It's advisable to agree on the fare with the driver before setting off to North Side. Once in North Side, getting around can be a bit more limited. There is no formal public transportation system like buses or trains that service the area. However, some resorts and accommodations may offer shuttle services to popular attractions or nearby amenities. If you're staying in a more remote location, having a rental car will be particularly beneficial. North Side itself is not particularly walkable as attractions and services are spread out, and there are limited sidewalks and pedestrian pathways. However, for those who enjoy leisurely strolls, the quiet roads and the beachfront can provide a pleasant walking experience, especially for short distances within the vicinity of your accommodation or along the coastline. For those looking to explore the waters around North Side, boat charters and water taxis can provide transport to other parts of the island or to some of the smaller cays for snorkeling and diving excursions. In summary, while North Side may not have the extensive transportation infrastructure of a major city, it is still accessible and navigable with a bit of planning. Renting a car is the most versatile option for getting around, but taxis and occasional shuttle services can also serve your transportation needs. Walking is best enjoyed for leisure rather than as a primary mode of transport due to the spread-out nature of the area.

North Side FAQs

North Side offers a variety of activities for visitors. You can explore the Crystal Caves, snorkel or dive at the famous barrier reef sites, relax on the beautiful beaches like Rum Point, visit the Queen Elizabeth II Botanic Park, or encounter wildlife at the Cayman Turtle Centre. For a cultural experience, you can also check out the local art galleries and craft markets.
The best time to visit North Side is from November to April during the dry season when the weather is warm and sunny. This is also the peak tourist season, so expect higher prices and more crowded attractions.
Visitors to the Cayman Islands must have a valid passport. Depending on your country of origin, you may also need a visa. It's important to check the latest entry requirements before traveling as they can change.
Yes, US dollars are widely accepted in North Side and throughout the Cayman Islands, although the local currency is the Cayman Islands dollar (KYD). Be aware of the exchange rate when making purchases.
North Side offers a range of dining options from casual beachside eateries to upscale restaurants. Seafood is a local specialty, and you can enjoy fresh catches along with international and Caribbean cuisine.
While there is some public transportation available, renting a car is recommended if you want to explore North Side and the rest of Grand Cayman at your own pace. Driving is on the left-hand side of the road.
Accommodations in North Side range from luxury resorts and villas to more modest guesthouses and vacation rentals. There's something to suit various budgets and preferences.

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Vacation Rentals Near North Side

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