Large group vacation rentals in North Side, Cayman Islands

Explore 285 large group vacation rentals, homes, and villas in North Side for your next getaway or business trip. With space for everyone, enjoy the comfort and privacy of a home designed for gathering, alongside premium amenities such as Air Condition Homes, Homes with Pools and Homes with Free Parking. Throughout your stay, spend time together, share meals, and relax in spacious living areas that make group travel feel cohesive. With options starting as low as $30 per night and homes offering up to 12 bedrooms and 14 bathrooms, it's easy to book a stay that fits your group. And with 24/7 local support and high-speed Wi-Fi, everyone stays connected and protected. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, making each trip more rewarding than the last. Book your next group getaway with Homes & Villas by Marriott.

285 Great for Groups in North Side

Maravilla

North Side, KY
4 Bedrooms 9 Guests
Aug 31 - Sep 5
$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 Grand Cayman Villas & Condos 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
Aug 31 - Sep 3
$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.

Willow Beach

North Side, KY
4 Bedrooms 12 Guests
Aug 31 - Sep 5
$799 night

*** PROPERTY OVERVIEW *** On the quiet North Side of Grand Cayman, you will find this newly built and freshly decorated bespoke villa. Welcome to Willow Beach! This spacious 4-bedroom, 4-bath villa sits on an elevated ridge overlooking a sandy beachfront with amazing backyard snorkeling. Water entry requires fins or pool shoes, as there are rocky ironshore areas along the waterline. Overlooking the ocean, the villa’s freshwater pool and tiled deck are elevated for enhanced privacy. Ample deck furniture, an outdoor shower, artificial grass terraces, plus an outdoor kitchen with a propane grill make for easy island living. The spacious open-concept great room links the living, dining, and kitchen areas with mesmerizing ocean views throughout. Quality furnishings and decor have been used throughout the property for an elegant and contemporary feel. The living area is furnished with a plush sectional sofa and high-definition Samsung Frame television with Cable programming & Sonos soundbar. Folding glass doors provide seamless indoor/outdoor living, allowing you to fill the great room with unobstructed oceanfront views. Each master suite has a vaulted ceiling, a king bed, and a large bathroom with ocean views! The gourmet kitchen comes equipped with modern appliances and everything needed to prep and serve a homemade meal. The formal dining table seats 10 guests easily, while the veranda dining table seats 6. The owner also provides a beachfront picnic table for seaside meals, with your toes in the sand. The villa’s 4-bedroom suites are separated by the great room, with 2 bedrooms on opposite ends of the home. **Sleeping Arrangements** (Licensed to sleep 12 guests or 8 adults max.) -- East Suite: oceanfront views, king bed, walkout access to the beach, vaulted ceilings, dual nightstands, ensuite with dual vanity, soaking tub, plus an open shower with water wand. -- Bunk Suite #1: queen bed + 2 upper twin bunk beds, island views, ensuite with shower. -- Bunk Suite #2: queen bed + 2 upper twin bunk beds, island views, ensuite with shower. -- West Suite: oceanfront views, king bed, walkout access to the beach, vaulted ceilings, dual nightstands, ensuite with dual vanity, soaking tub, plus an open shower with water wand. -- Bunk beds are suitable for children only. Willow Beach is equipped with high-speed internet for work-from-home professionals and multiple streaming devices. Only 10 minutes from the Rum Point Club to the west, Willow Beach is very convenient to a small grocery store, a handful of restaurants, and our Guest Services Welcome Center with a private fitness center. Click the Map tab for other nearby attractions. With its private pool, modern interiors, and central location on North Side, Willow Beach is an ideal home-away-from-home in the Caribbean, with plenty of style. *Note: Single and tandem kayaks are available for discounted rental. A signed waiver is required. ======= ***RATE DETAILS*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service Fee is added to all rates. -- Accidental Damage Protection added to all 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. *** GUEST SERVICES *** The Service Fee includes your Guest Services Membership. Member Benefits -- Complimentary use of snorkel equipment during your stay -- Complimentary pack-n-plays, booster seats, & baby gates -- 10% Advance Booking Discount towards a private charter -- Guest discount card for 10% savings with local vendors. -- Complimentary early check-in, if no check out on same day -- 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 -- Referral to preferred vendors, guest services desk assistance -- Single or tandem kayaks available at discounted rates; signed waiver required. ================= ***Nearby Points of Interest*** -- 2-minute drive west to the nearest grocer, Chisholm’s Grocery -- 2-minute drive east to Over the Edge restaurant and Cayman Crystal Caves -- 3.5 miles from our Guest Services Welcome Center, plus Jacques Scott Wine & Spirits -- 6 miles west to the Rum Point Club and the Bioluminescent Bay -- 6.5 miles to the Kaibo Beach Bar & Grill & Starfish Point -- 7 miles east to the nearest supermarket, Foster’s Express, plus The Italian Kitchen, and two beach resorts, Morritt’s and The Reef. -- 9.5 miles to Tukka East Restaurant & Bar and the Cayman Parrot Sanctuary -- 10 miles to La Casita Taco & Tequilla Bar -- 21 miles (39-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. ***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 harmless floating seaweed that has increased in frequency during the summer. Our owners make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. Should sargassum weed 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.

Coastal Charm

North Side, KY
3 Bedrooms 9 Guests
Aug 31 - Sep 5
$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.

KiToCay Villa

Old Man Bay, KY
3 Bedrooms 5 Guests
Aug 31 - Sep 5
$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. ***Grand Cayman Villas & Condos 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 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

Twin Palms

Rum Point, KY
7 Bedrooms 14 Guests
Aug 31 - Sep 5
$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. ***Grand Cayman Villas & Condos 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.

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

Cayman Sands

Old Man Bay, KY
5 Bedrooms 14 Guests
Aug 31 - Sep 5
$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. ***Grand Cayman Villas & Condos 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.

Halcyon Point

Old Man Bay, KY
5 Bedrooms 10 Guests
Aug 31 - Sep 4
$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.

Olympus Villa

Rum Point, KY
5 Bedrooms 12 Guests
Aug 31 - Sep 5
$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. ***Grand Cayman Villas & Condos 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.

Spacious 3 Bd Beachfront Ground Flr Condo w/ Pool

North Side, North Side, KY
3 Bedrooms 6 Guests
Aug 31 - Sep 5
$528 night

Welcome to On The Bay #101. This serene and luxurious 3-bedroom, 3-bath ground-floor condo is set directly on the beachfront. Step from your screened patio to hammocks waiting just outside, stroll onto soft white sand, or relax at the beachfront pool overlooking the cove. On The Bay’s protected cove makes swimming and water access easy and calm, perfect for families and snorkelers. Located on Cayman’s tranquil North Side, enjoy sweeping ocean views and island-style comforts. This upgraded 3-bedroom, 3-bath beachfront condo at On The Bay #101 sits directly on the sands of Old Man Bay on Grand Cayman’s North Side. While the exterior showcases classic Caribbean charm, the owners have transformed the interior with modern amenities and elegant finishes. The open living area features plush seating, a custom bar, and sweeping ocean views, creating an inviting space to unwind. Each bedroom includes its own private bathroom for added comfort. The master suite offers a spacious retreat with a king bed and a luxurious spa-style bath complete with a large freestanding soaking tub. The second bedroom features a queen bed with an en-suite bathroom, while the third bedroom provides a cozy double bed and its own private bath. The fully equipped kitchen includes modern appliances and all essentials for easy meal prep. Step onto the screened-in patio and enjoy plush outdoor seating, a perfect spot for morning coffee or sunset cocktails. Just beyond the patio, hammocks sway in the breeze, the beachfront pool awaits, and a protected cove offers calm, easy access to the water, ideal for swimming and snorkeling. Unit #101 blends modern comfort with serene coastal living, offering a beautifully updated beachfront escape in one of Cayman’s most peaceful locations. 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. 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. Please note that the owners of this rental live on the property in a separate unit for approximately six months each year. During this time, we will continue to provide full management of the rental; however, the owners will be onsite and available to assist in the event of an emergency. This property is not suitable for children under the age of 12 years old. 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.

Penthouse 2 Bd/Bth Beachfront Condo w/ Heated Pool

North Side, North Side, KY
2 Bedrooms 6 Guests
Aug 31 - Sep 2
$200 night

Experience the Ultimate Beachfront Getaway and truley find your Happy Place at On the Bay # 312. Discover unparalleled luxury and serenity at this expansive 2-bedroom, 2-bathroom beachfront condo, nestled within the prestigious On the Bay complex in Old Man Bay, North Side, Grand Cayman. Renowned for its immaculate tropical landscaping and pristine white sand beach, On the Bay stands as one of the premier condo developments along the northern coastline. Experience the Ultimate Beachfront Getaway and truely find your Happy Place at On the Bay, Grand Cayman Discover unparalleled luxury and serenity at this expansive 2-bedroom, 2-bathroom beachfront condo, nestled within the prestigious On the Bay complex in North Side, Grand Cayman. Renowned for its immaculate tropical landscaping and pristine white sand beach, On the Bay stands as one of the premier condo developments along the northern coastline. Tropical Paradise Awaits Set within a sheltered cove, guests can effortlessly transition from lush gardens to the crystal-clear waters teeming with vibrant marine life. Ideal for snorkeling enthusiasts, the warm Caribbean Sea offers an underwater world waiting to be explored. After a day of adventure, relax at the sprawling complex pool, a serene oasis perfect for unwinding amidst gentle tropical breezes under the shade of swaying coconut palms. Luxurious Living Spaces Inside, the condo features two generously sized bedrooms, each with a spacious ensuite bathroom, ensuring privacy and convenience. With over 1,685 square feet of living space, including a sizeable balcony offering uninterrupted views of the Caribbean Sea, this unit provides ample room for relaxation and enjoyment. The fully equipped kitchen, complete with stunning ocean vistas, inspires culinary adventures, making home-cooked meals a delightful experience. Elegant Comfort The expansive Master bedroom boasts a plush king-size bed, complemented by nightstands, a desk, chest of drawers, and a lavish ensuite bathroom with a jet tub, shower, toilet, and walk-in closet—everything needed for a stress-free vacation. The second bedroom offers two full beds, ensuring comfortable accommodations for additional guests, with an adjoining ensuite bathroom featuring a jetted jacuzzi tub for added luxury. Prime Location for Island Exploration Conveniently located just 10 minutes from Cayman Kai and Rum Point, as well as various restaurants, attractions, and amenities in East End and Bodden Town, Old Man Bay serves as an ideal base for exploring the island’s treasures. Within a short drive, guests can visit the Botanical Gardens, Crystal Caves, and the Mastic Trail, immersing themselves in the island’s natural splendor. With George Town and the airport a pleasant 45-minute drive away, a rental car is highly recommended for ease of access and exploration. Your Dream Vacation Awaits Immerse yourself in the beauty and tranquility of Grand Cayman. Book your stay at On the Bay, where luxury, adventure, and relaxation converge to create the perfect beachfront getaway. The entire condo, pool, beach and grounds. 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.

Gypsy Villa

Rum Point, KY
4 Bedrooms 10 Guests
Aug 31 - Sep 5
$1,029 night

***PROPERTY OVERVIEW*** Welcome to Gypsy, a luxurious island getaway! This elegant Caribbean-themed villa is a true tropical paradise with a private oceanfront pool and backyard beachfront. Gypsy’s backyard oasis offers a private haven above the beach, ensuring your relaxation and privacy. Stairs lead down to a beautiful sandy beach, perfect for sunbathing. The pool deck includes sun beds for your convenience, and large hedges and grassy lawns providing seclusion during your stay. Optional pool heat is available during the winter at $50 per day for added comfort. As you enter the foyer, the tall glass doors beckon your gaze to the private pool area and the stunning Caribbean Sea beyond. Gypsy offers over 4,000 sq ft of living space, with an additional 3,000 sq ft of outdoor paradise, accommodating up to 10 guests across four bedrooms. Sleeping Arrangements (Sleeps 10 guests max.) -- Primary Suite: king bed, ocean views, walk-out access to the pool deck, walk-in closet, ensuite with double vanity, soaking tub, and separate walk-in shower. -- Bedroom #2: king bed, garden views, ensuite with walk-in shower. -- Bedroom #3: queen bed, garden views, ensuite with shower bath. -- Bedroom #4: 2 queen beds, garden views, shares adjacent hall bath equipped with double vanity and walk-in shower. Gypsy’s living areas boast astounding views, high ceilings, and plenty of natural light. The living room and family room offer ample seating for relaxation while enjoying the mesmerizing views. If you love music, the grand piano in the family room can be unlocked for your enjoyment. The gourmet kitchen is a chef’s dream, equipped with modern appliances, a double oven, a built-in Subzero refrigerator, a Keurig coffeemaker, and plenty of counter space. A dining table with seating for 10 allows for memorable meals with your loved ones. A propane grill is available on the pool deck for island cookouts. Please note that the owner does not permit pets, smoking, or events with invited guests on the property to ensure a serene and peaceful atmosphere. Don’t miss the chance to embrace the Caribbean dream at Gypsy! ***NOTES*** -- A Cleaning Fee is added for all stays due to enhanced cleaning and sanitation. -- Tandem kayaks and SeaView boards 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 cleaning fee is added to all rates. ***BOOKING RULES*** -- Christmas & New Year’s are split into two 7-night rental periods. Please inquire with 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*** The 12.90% Guest Service Fee includes your Guest Services Membership. Member Benefits -- Complimentary snorkel equipment for use during your stay. -- 10% Advance Booking Discount towards a private snorkel or dive charter. -- Guest benefit card for 10% discount with our preferred vendors. -- Jacques Scott Wine & Spirits pre-order & complimentary hold at check-in -- Centralized on-island Guest Services & Welcome Center. -- Unlimited use of Private Fitness Center (18+ yrs.). -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Referral to preferred vendors, guest services desk assistance At-Villa Benefits -- Complimentary pack-n-plays, booster seats, & baby gates -- Complimentary early check-in, if no check-out on the same day. -- Day-after-arrival guest services follow-up. -- Gilchrist & Soames bath products. -- Assistance coordinating private chefs, family-style cooks, babysitting, or family photography -- $1,500 of Accidental Villa Damage Protection -- Pre-stocking of groceries & beverages (delivery fee applies) -- Tandem kayaks are available for discounted rental* *Signed waiver required. =============== ***GETTING AROUND*** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town. Plus, there is no Uber or Lyft in Cayman. For rental cars, we recommend Budget Cayman, Marshalls, or Hertz. ***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 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.

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

North Side, North Side, KY
3 Bedrooms 6 Guests
Aug 31 - Sep 3
$280 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

Fischers Reef

Rum Point, KY
8 Bedrooms 20 Guests
Nov 21 - 28
$6,089 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. ***Grand Cayman Villas & Condos 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.

Luxury 3bd Beach Front, # 4 Green, Stunning Views

North Side, Grand Cayman, KY
3 Bedrooms 8 Guests
Aug 31 - Sep 2
$284 night

Perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations and is conveniently located near renowned Stingray City, Rum Point and Kaibo’s restaurants, beaches and water sport activities. Bask on the white sand beach, enjoy the pool, swim and snorkel with a myriad of sea life, or simply lounge in your hammock snoozing away the day. Each one of the five homes at this intimate enclave at Ocean Paradise is characterized by a unique color and Green blends in perfectly with its lush tropical surroundings. The three-bedroom, three-bathroom oasis features spacious accommodations and breathtaking Caribbean views that will leave you speechless. Enjoy a fully equipped kitchen complete with modern appliances and ample seating for you and your guests. The spacious living area features comfortable seating, high-end electronics, and tasteful decor to create a relaxing and inviting atmosphere. Each of the three bedrooms is beautifully designed with plush bedding and comfortable furnishings, ensuring a peaceful night’s sleep. Whether you’re lounging on the private balcony, taking a dip in the nearby pool, or exploring the local area, this vacation rental is the perfect retreat for your next getaway. Home #4 at Ocean Paradise is one of our two premier beachfront homes with spectacular views of Grand Cayman’s northern coastline from almost every room in the house. Entire Home. 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. Upon booking, you will receive a key code for the keyless entry system, allowing for a seamless and convenient self-check-in process at this exquisite property. While it may not be necessary for everyone, we recommend bringing sea shoes. 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.

Coral Kai

Rum Point, KY
5 Bedrooms 10 Guests
Aug 31 - Sep 5
$1,144 night

***Property Overview*** Coral Kai is directly oceanfront in Rum Point on the north coast. This large one-story villa offers a sizable sandy beach that’s perfect for long walks or just a lazy afternoon. Excellent snorkeling is just steps from the back door! The large, oceanfront freshwater pool is elevated, allowing guests to soak in the wonderful ocean views while they swim. Coral Kai is less than a mile from the Rum Point Club, so guests can easily step out for water sports, drinks, lunch, or dinner. Coral Kai’s full-width, shaded veranda offers a place to relax in outdoor sectional sofas or lounge chairs; cool tile floors and outdoor dining tables make it the perfect place to unwind after a day of surf and sand. A propane grill next to the pool makes for effortless outdoor dining. ***Bedroom Configuration*** (Sleeps 10 guests total) -- Oceanfront King Suite: Gorgeous suite with a king bed, doors to the pool deck, stunning ocean views, two comfy chairs, and an ensuite bath with a soaking tub. -- Oceanfront Queen Suite: Ocean view suite with a queen bed, doors to the pool deck, spectacular ocean views, and an ensuite bath with a combination shower/bathtub. -- Garden View King Suite: Garden view suite with a king bed, TV, and an ensuite bath with a walk-in shower. -- Garden View Queen Suite: Garden view suite with a queen bed and an ensuite bath with a combination shower/bathtub. -- Twin Bedroom: Garden view bedroom with two twin beds and a bath next door. Twin beds can be converted to a king upon request. ***Coral Kai’s Unique Features*** -- Oceanfront windows and french glass doors facing the sea flood Coral Kai with Caribbean sunshine year-round. -- The recently redecorated interior gives the home an airy, beach house feel without sacrificing luxury or comfort. -- The living, dining, and kitchen areas all offer wonderful views of the Caribbean Sea. -- An enormous sectional sofa and a large flat-screen TV in the oceanfront living room allow everyone to hang together at the end of the day, whether they want to watch a movie or just relax. -- Sizable, open kitchen with modern appliances, plenty of counter space, and bar seating for quick meals or evening drinks! Dishware, cookware, cutlery, and a coffeemaker are all provided. -- Separate den with an additional flatscreen TV is perfect for kids, teenagers, or anyone who wants to get away for a few moments. -- Elevated veranda with outdoor sectional sofa and dining area. -- Superb wedding venue for small ceremonies. Excellent for large families, or 2-5 couples. Twin beds can be converted to a king upon request. Pool heat (winter only) is available for a $250 per week surcharge. NOTES: Bicycles and kayaks are available for discounted rental. Signed waiver 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 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 ***Grand Cayman Villas & Condos 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 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.

White Cottage

East End, KY
5 Bedrooms 11 Guests
Aug 31 - Sep 5
$950 night

*** PROPERTY OVERVIEW *** Welcome to White Cottage. This contemporary, open-concept villa offers guests an opportunity to spend their vacation amid sumptuous interiors with smart-home technology, gated privacy, and scenic Caribbean views. An oceanfront wall of glass and a screened porch blend stunning views with protected, intimate spaces for quintessential indoor-outdoor island living. With heavy landscaping and no neighbors on either side, White Cottage will be your private oasis after a day in the sun and water. A 100-foot private dock with a thatched cabana provides a relaxing spot above the waves. Enjoy sunsets, happy hour, or alfresco dining above the waves. Intrepid snorkelers can use the dock ladder for gentle water entry before exploring the nearby reefs. All guests receive free snorkel gear upon check-in at our Welcome Center. Inside, the home’s kitchen comes fully equipped with an electric cooktop, dual ovens, a built-in refrigerator, microwave, dishwasher, and twin wine/beverage fridges. Prepare a home-style dinner or hire a private chef for a night of in-villa fine dining. A large formal indoor dining table seats 8 guests. The outdoor dining table on the screened porch seats 8 guests for meals with oceanfront views. White Cottage’s 5 bedrooms are spread across the home’s upper and lower levels. ***Sleeping Arrangements*** (Sleeps 11 guests total; 10 adults max.) -- Bedroom 1: primary suite, king bed, ocean views, walk-out access to the porch, SmartTV, SONOS audio, ensuite with dual vanity, oversized tub, and separate shower featuring a full body shower spa. -- Bedroom 2: king bed, ocean views, walk-out access to the porch and pool deck, SmartTV, SONOS audio, shares the adjacent bathroom equipped with a shower bath. -- Bedroom 3: twin-over-twin bunk beds with a third twin trundle bed, SmartTV, SONOS audio, shares the adjacent bathroom equipped with a shower bath. -- Bedroom 4: upper-level, queen bed, SmartTV, desk + chair, shares adjacent hall bathroom equipped with full-body shower spa. -- Bedroom 5: upper-level, queen bed, SmartTV, sofa chair, shares adjacent hall bathroom equipped with full-body shower spa. ***White Cottage’s Notable Features*** -- 50-foot, lap-style pool with sundeck furnished with table & chairs, sun loungers, and a large shade umbrella -- Barefoot beachfront with access to shallow water; deeper water requires pool shoes or fins -- L-shaped screened oceanfront porch with dining table, and sitting area -- High-speed fiber internet plus a desk + chair for remote professionals -- SmartTVs in the living area and all bedrooms -- SONOS audio system throughout -- Soft evening LED lighting throughout Located in the middle of the island, you are only 8 minutes from the Botanical Gardens, Cayman Crystal Caves, and the fitness studio at our Welcome Center. Restaurants and 5-star diving experiences in the East End are only 10 minutes away! Note: Additional single/tandem kayaks are available for discounted rental. Signed waiver 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. -- 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. *** GRAND CAYMAN VILLAS & CONDOS 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 -- $3,000 of Accidental Villa Damage Protection -- Complimentary pack-n-plays, booster seats, & baby gates -- Single & Tandem kayaks are available for discounted rental (signed waiver required). ====================== ***NEARBY POINTS OF INTEREST*** -- 31 minutes from Owen Roberts Airport (GCM) -- 4 minutes from our Grand Cayman Villas & Condos Welcome Center -- 18 minutes to the nearest supermarket, Foster’s Countryside -- 10 minutes to La Casita restaurant -- 13 minutes to Tukka East restaurant -- 16 minutes to The Italian Kitchen restaurant -- 1 minute to Heritage Beach -- 18 minutes to Spotts Public Beach -- 20 minutes to Rum Point Beach (temporarily closed) -- 24 minutes to the Kaibo Beach Bar & Grill and Starfish Point ***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 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.

Rum Point Resort Penthouse #504

Rum Point, KY
3 Bedrooms 8 Guests
Aug 31 - Sep 3
$841 night

*** PROPERTY DESCRIPTION *** Fifth Floor Penthouse | 2,620 sq. ft. All Rum Point Resort condos feature sleek finishes, designer decor, and an open-concept layout maximizing space, natural light, and stunning ocean views. All the comforts of home are included in this 2,620 sq. ft. penthouse condo including gourmet kitchen appliances, quartz countertops, SmartTVs throughout, and a private open-air oceanfront balcony. All condos strike the perfect balance of modern luxury and seamless indoor/outdoor island living. Central air conditioning and high-speed wifi will keep you cool and connected during your stay. Beyond the entryway foyer, the home flows into a spacious open-concept great room encompassing the living, dining, and kitchen areas. Forever blue ocean views from the great room and primary suite will leave you breathless. Vaulted ceilings and crisp coastal decor throughout accentuate the island scenery. The living area includes a comfy sectional sofa, a large SmartTV, a tray ceiling with a ceiling fan, and coastal decor. Walk out from the living area onto the private balcony overlooking the resort’s pool deck and beachfront. The balcony is also equipped with a retractable sunshade above an aluminum pergola for relief from the island sun. The gourmet kitchen features a suite of Thermador appliances, plus countertop appliances and a kitchen island with breakfast bar seating. Cookware, dishware, glassware, and cutlery also come provided. An outdoor dining table with seating for 6 is furnished on the private balcony for meals with sweeping oceanfront views. The Rum Point Resort fits all condos with blackout window shades, the finest Egyptian cotton bedding, hypoallergenic pillows, duvets, and sumptuous robes. ***Sleeping Arrangements*** (Sleeps 8 guests; 6 adults max.) -- Primary Suite: king bed, ocean views, walk-out access to a private open-air balcony, SmartTV, walk-in closet, desk + chair, ensuite with dual vanity, soaking tub, and shower. -- Guest Suite: king bed, SmartTV, walk-in closet, ensuite with soaking tub and shower. -- Guest Suite #2: queen bed, SmartTV, ensuite with shower. -- Additional bedding: sleeper sofa in the living area suitable for kids. Crib or pack-n-play provided upon request; children under 2 do not count towards occupancy. There is also a rarely used 5th-floor open-air owner’s terrace with dining tables and seating for sunset dinners with 270-degree island views of Cayman Kai, North Sound, and George Town in the distance. The terrace is also a serene setting for a quiet read with elevated island views. Trade the crowds of Seven Mile Beach for an escape to Cayman’s quieter side where life is easy and not so fast. ***Additional Resort Amenities*** -- 500 feet of beachfront with daily beach umbrella, chair, and towel service. -- Resort pool deck with heated infinity pool. -- Resort dock with cabana and ladder for gentle water entry for snorkeling and swimming. -- Our new on-resort restaurant, Blue Flame, is open from 11:00 a.m. to 11:00 p.m. for lunch and dinner service. -- Private chef dining options available*. -- Front desk staff for local recommendations, pre-arrival grocery stocking, chartered excursions, and more*. -- Access to the 5th-floor Owner’s Terrace for group events or sunset dinners*. -- On-site fitness center (18+ and over). -- On-site wellness suite for spa treatments or massage*. -- Xbox Gaming Console or DVD Player Available at the Front Desk+. -- Complimentary snorkel equipment provided during your stay+. -- Complimentary bike share for cruising the Cayman Kai neighborhood+. Discover why the Rum Point Resort is Cayman’s hidden 5-star gem! Resort Amenities Notes: * Pre-arrival reservations are required; additional fees apply. + Provided on a first-come, first-served basis. Cannot be reserved before arrival. *** RATE DETAILS *** -- 13% Occupancy Tax added to all rates. -- 10% Resort Fee is added to all rates. -- Accidental Damage Protection added to all rates. *** BOOKING RULES *** -- Christmas & New Year’s are split into two separate rental periods. Please inquire about your dates before booking for the holidays. -- Guests must be 25 years or older to book and occupy the unit during the entire stay. -- Check-in: 4:00 pm. -- Check-out: 11:00 am. *** NEARBY POINTS OF INTEREST *** -- The resort is next door to the Rum Point Club for food + drinks, snorkeling, watersport rentals, and Stingray City excursions. -- The resort is adjacent to Cayman’s Bioluminescent Bay for nighttime kayak tours. -- 1.2 miles to the Kaibo Beach Bar & Grill and The Kaibo Marina. -- 1.7 miles south to Starfish Point -- 4.4 miles to the nearest market, Chisholm’s Grocery. -- 6.2 miles east to Over the Edge restaurant -- 6.7 miles to Cayman Crystal Caves -- 12.5 miles to the nearest supermarket, Foster’s Market -- 26 miles (49-minute drive) from Owen Roberts Airport (GCM) *** GETTING AROUND *** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget, Avis, Marshalls, or Hertz. *** DAY TRIPPING *** Cayman Ferries operates daily water taxis departing from the Kaibo Marina to Camana Bay. Perfect for day trips to Seven Mile Beach or shopping excursions at Camana Bay. Download their app to purchase your tickets in advance. Just be sure to make it back for the return voyage across the sound!

Peace & Kai It

Rum Point, KY
3 Bedrooms 6 Guests
Nov 30 - Dec 5
$742 night

***Property Overview*** This redecorated and lively 3-bedroom, 2-bath beach cottage epitomizes easy island living in beautiful Cayman Kai. Located on the shores of Cayman’s Bioluminescent Bay, the new owners have updated just about everything and also provided complimentary kayaks! As you enter the home, your eyes are drawn through a wall of sliding glass doors to the shimmering turquoise blue waters. Coconut palm trees, an elevated sundeck, a private dock, and a seaside hammock beckon you to kick off your shoes and relax. Let the vacation begin! A spacious living room and large kitchen provide all the comforts of home with new furniture and modern appliances. Dual-zone air conditioning, fiber-optic wifi, and SmartTVs will keep everyone cool and connected across their devices. Work-from-home professionals will enjoy the home’s high-speed wifi providing fiber-optic speeds for multiple users and devices. This single-level home positions the primary suite on one side of the home with two additional bedrooms on the opposite end. ***Sleeping Arrangements*** (Sleeps 6 guests total) -- Primary Suite - king bed, water views, SmartTV, ceiling fan, walk-out access to the screened porch, ensuite with shower bath. -- Guest Bedroom #1 - king bed, water views, SmartTV, walk-out access to the screened porch, shares hall bathroom equipped with a walk-in shower. -- Guest Bedroom #2 - 2 extra-large twin beds, island views, SmartTV, shares hall bathroom equipped with a walk-in shower. Twin beds can be fitted into a king upon request only. The newly-renovated kitchen comes complete with modern stainless appliances and a breakfast bar with seating for 4. A separate bar complete with an under-counter beverage fridge and a high-speed blender will keep your favorite frozen cocktails flowing. A full laundry room sits adjacent to the kitchen. The full-width screened patio and raised sun deck are furnished with al-fresco dining tables and comfortable lounge seating. The screen porch has western-facing views to enjoy spectacular sunset viewings at cocktail hour. A charcoal grill comes provided for island cookouts. Enjoy outdoor dining for 8 on the screened patio with 180-degree water views. With sea breezes all year round, it really does not get much better than this! Guests are asked to respect the villa’s non-smoking policy which includes all screened areas. Owners provide kayaks on a complimentary basis for use during your stay. Additional kayaks can be rented at friendly rates. Launch off the home’s private dock to explore the glowing waters of Bioluminescent Bay on moonless nights. Book a private charter to Stingray City and have the captain collect and drop you off on the home’s private dock. Peace & Kai It is a great option for families and group getaways. The adjacent 4-bedroom property, S’Kai Blue, can be combined with Peace & Kai It to sleep a total of 17 guests, or 14 adults, with an added private pool! Please contact us for more info on this bundled configuration. ***IMPORTANT NOTES*** -- A Cleaning Fee may be required due to enhanced cleaning, sanitation, and inspection protocols. -- Additional 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. -- 10% Guest Service Fee 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 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. ***Grand Cayman Villas & Condos 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 -- 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 -- $500 of Accidental Villa Damage Protection -- Additional kayaks and stand-up paddleboards (SUPs) available for discounted rental* *Signed waiver required. =================== ***Nearby Points of Interest*** -- Home is located on the island’s Bioluminescent Bay -- 15-minute walk to the Rum Point Club for snorkeling, watersports, and light dining. -- 10-minute walk to the Kaibo Beach Bar & Grill -- 12-minute walk south to Starfish Point -- 5.0 miles to the nearest general store, Chisholm’s Grocery -- 6.9 miles east to Over the Edge restaurant -- 7.4 miles east to Cayman Crystal Caves -- 9.4 miles from our Grand Cayman Villas & Condos Welcome Center -- 13.2 miles to the nearest supermarket, Foster’s Market -- 26.2 miles (51-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 Avis, Marshalls, or Budget. ***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 before your arrival. Should sargassum be extremely heavy behind your property, we will contact the owner for alternative solutions, which may include a partial refund or relocation. We try our best to work around Mother Nature.

Luxury 3bd Beach View, # 3 Blue, Stunning Views

North Side, Grand Cayman, KY
3 Bedrooms 9 Guests
Aug 31 - Sep 2
$281 night

Perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations and is conveniently located near renowned Stingray City, Rum Point and Kaibo’s restaurants, beaches and water sport activities. Bask on the white sand beach, enjoy the pool, swim and snorkel with a myriad of sea life, or simply lounge in your hammock snoozing away the day. With its mesmerizing blue exterior that blends seamlessly into the breathtaking ocean views, this home exudes a sense of tranquility and serenity. The three-bedroom, three-bathroom oceanfront home is perfectly suited for families. Each one of the five homes at this intimate enclave at Ocean Paradise is characterized by a unique color and Blue offers its own unique charm. The fully equipped kitchen features high-end appliances, ample counter space, and all the necessary cookware and utensils to whip up a culinary masterpiece. The living area is spacious and cozy, featuring plush sofas and chairs, a large coffee table, and tasteful decor that creates a warm and inviting atmosphere for relaxation and entertainment. An outdoor terrace offers the perfect spot to relax and soak up the salty sea breeze with stunning ocean views. Entire Home. 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. Upon booking, you will receive a key code for the keyless entry system, allowing for a seamless and convenient self-check-in process at this exquisite property. While it may not be necessary for everyone, we recommend bringing sea shoes. 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.

Rum Point Resort #308

Rum Point, KY
2 Bedrooms 4 Guests
Aug 31 - Sep 3
$575 night

*** PROPERTY DESCRIPTION *** 3rd Floor Condo | 1,350 sq. ft. All Rum Point Resort condos feature sleek finishes, designer decor, and an open-concept layout maximizing space, natural light, and stunning ocean views. All the comforts of home are included in this 1,350 sq. ft. 1-bedroom + den premium condo including gourmet kitchen appliances, quartz countertops, SmartTVs for streaming, and a private oceanfront balcony. All condos strike the perfect balance of modern luxury and seamless indoor/outdoor island living. Central air conditioning and high-speed wifi will keep you cool and connected during your stay. Beyond the entryway foyer, the home flows into a spacious open-concept great room encompassing the living, dining, and kitchen areas. Forever blue ocean views from the great room and primary suite will leave you breathless. Crisp coastal decor throughout accentuates the island scenery. The living area includes a plush sectional sofa, a large SmartTV, a tray ceiling with a ceiling fan, and stunning ocean views. Walk out from the living area onto the private roofed balcony overlooking the resort’s beachfront. The gourmet kitchen features a suite of Thermador appliances, and countertop appliances, plus a kitchen island with breakfast bar seating. Cookware, dishware, glassware, and cutlery also come provided. An outdoor dining table is furnished on the private balcony for meals with sweeping oceanfront views. An indoor dining table is also furnished just off the kitchen. The Rum Point Resort fits all condos with blackout window shades, the finest Egyptian cotton bedding, hypoallergenic pillows, duvets, and sumptuous robes. ***Sleeping Arrangements*** (Sleeps 6 guests; 4 adults max.) -- Primary Suite: king bed, ocean views, walk-out access to the ocean balcony, SmartTV, walk-in closet, ensuite with oversized soaking tub, and shower. -- Bunk Suite: full-over-full bunk beds, SmartTV, ensuite with shower. There is also a rarely used 5th-floor open-air owner’s terrace with dining tables and seating for sunset dinners with 270-degree island views of Cayman Kai, North Sound, and George Town in the distance. The terrace is also a serene setting for a quiet read with elevated island views. Trade the crowds of Seven Mile Beach for an escape to Cayman’s quieter side where life is easy and not so fast. ***Additional Resort Amenities*** -- 500 feet of beachfront with daily beach umbrella, chair, and towel service. -- Resort pool deck with heated infinity pool. -- Resort dock with cabana and ladder for gentle water entry for snorkeling and swimming. -- Our new on-resort restaurant, Blue Flame, is open from 11:00 a.m. to 11:00 p.m. for lunch and dinner service. -- Private chef dining options available*. -- Front desk staff for local recommendations, pre-arrival grocery stocking, chartered excursions, and more*. -- Access to the 5th-floor Owner’s Terrace for group events or sunset dinners*. -- On-site fitness center (18+ and over). -- On-site wellness suite for spa treatments or massage*. -- Xbox Gaming Console or DVD Player Available at the Front Desk+. -- Complimentary snorkel equipment provided during your stay+. -- Complimentary bike share for cruising the Cayman Kai neighborhood+. Discover why the Rum Point Resort is Cayman’s hidden 5-star gem! Resort Amenities Notes: * Pre-arrival reservations are required; additional fees apply. + Provided on a first-come, first-served basis. Cannot be reserved before arrival. *** RATE DETAILS *** -- 13% Occupancy Tax added to all rates. -- 10% Resort Fee is added to all rates. -- Accidental Damage Protection added to all rates. *** BOOKING RULES *** -- Christmas & New Year’s are split into two separate rental periods. Please inquire about your dates before booking for the holidays. -- Guests must be 25 years or older to book and occupy the unit during the entire stay. -- Check-in: 4:00 pm. -- Check-out: 11:00 am. *** NEARBY POINTS OF INTEREST *** -- The resort is next door to the Rum Point Club for food + drinks, snorkeling, watersport rentals, and Stingray City excursions. -- The resort is adjacent to Cayman’s Bioluminescent Bay for nighttime kayak tours. -- 1.2 miles to the Kaibo Beach Bar & Grill and The Kaibo Marina. -- 1.7 miles south to Starfish Point -- 4.4 miles to the nearest market, Chisholm’s Grocery. -- 6.2 miles east to Over the Edge restaurant -- 6.7 miles to Cayman Crystal Caves -- 12.5 miles to the nearest supermarket, Foster’s Market -- 26 miles (49-minute drive) from Owen Roberts Airport (GCM) *** GETTING AROUND *** A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Marshalls, or Hertz. *** DAY TRIPPING *** Cayman Ferries operates daily water taxis departing from the Kaibo Marina to Camana Bay. Perfect for day trips to Seven Mile Beach or shopping excursions at Camana Bay. Download their app to purchase your tickets in advance. Just be sure to make it back for the return voyage across the sound!

Vacation Rentals in North Side by Amenities & Features

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Vacation Rentals Near North Side

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