North Side, Cayman Islands Vacation Rentals

Explore 290 vacation rentals, homes, and villas in North Side for your next getaway or business trip. Experience the privacy of a home with premium amenities such as Air Condition Homes, Homes with Pools and Homes with Free Parking, designed for a more comfortable and convenient stay. Every home is curated and professionally managed, with 24/7 local support, high-speed Wi-Fi, and premium linens included. With homes starting as low as $30 per night and featuring up to 12 bedrooms and 14 bathrooms, there's an option for every trip, from family vacations and group getaways to extended stays. However you're looking to experience your stay, Homes & Villas by Marriott has your next vacation home waiting. Marriott Bonvoy members can also earn and redeem points on every booking.

290 Vacation Rentals in North Side

Maravilla

North Side, KY
4 Bedrooms 9 Guests
Aug 21 - 26
$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 before your arrival.

Beautiful 3 Bd Beachfront Home North Side Sleeps 7

North Side, Grand Cayman, KY
3 Bedrooms 7 Guests
Aug 22 - 25
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. 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 21 - 26
$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 21 - 26
$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 experience floating ocean debris and sargassum. Sargassum is a harmless seaweed that has increased due to warming waters. 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. We try our best to work around Mother Nature.

KiToCay Villa

Old Man Bay, KY
3 Bedrooms 5 Guests
Aug 21 - 26
$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: -- A Cleaning Fee may be required due to enhanced cleaning, sanitation, and inspection protocols. -- Single or tandem kayaks 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’s largely seasonal in summer. Our owners 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 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

Timeless Paradise

Rum Point, KY
11 Bedrooms 28 Guests
Aug 21 - 26
$3,444 night

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

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

Twin Palms

Rum Point, KY
7 Bedrooms 14 Guests
Aug 21 - 26
$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.

Penthouse 2 Bd/Bth Beachfront Condo w/ Heated Pool

North Side, North Side, KY
2 Bedrooms 6 Guests
Aug 24 - 26
$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.

Rip Kai Villa

Rum Point, KY
9 Bedrooms 22 Guests
Aug 23 - 28
$3,163 night

===> PROPERTY OVERVIEW <=== Welcome to Rip Kai Villa, an extraordinary oceanfront estate in Rum Point designed for unforgettable group getaways, extended family reunions, and milestone celebrations. Spanning over 8,000 square feet of seamless indoor and outdoor living, this private sanctuary offers complete luxury and privacy across five Great House suites, two detached Veranda Suites, and a separate two-bedroom Guest Cottage featuring its own living areas and kitchenette. The vacation experience begins with an airport greeting by a professional driver and a 28-seat mini-coach (7-night minimum stay required). Our on-island concierge can coordinate with your rental car company for delivery of your vehicles to the villa in advance. Pre-stocking the home with groceries and beverages is also a popular add-on, as is having our concierge coordinate in-villa chef or butler services for a few nights of stress-free gourmet dining. The crown jewel of Rip Kai is its expansive resort-style pool deck. Step out onto a private backyard paradise, lined with shaded pergolas, a tiered sundeck with 12 chaise lounges, and an invigorating pool and hot tub overlooking reef-protected waters. Perfect for alfresco dining, the large outdoor kitchen and entertainment pavilion features a built-in gas grill, bar seating, dual Smart TVs, and an outdoor dining table under the shade of the wraparound veranda. Steps away on the pool deck, guests of all ages can hang out in the fully equipped game room—complete with a ping pong table, dartboard, Smart TV, and full bathroom. Kids will love their own private paradise at the outdoor playground, equipped with a swing set, slide, and roofed play fort, while adults can enjoy a game on the beachfront volleyball court. Whether you are relaxing by the pool, cooking outdoors, or enjoying beach games, Rip Kai offers the ultimate luxury retreat on Grand Cayman. Inside, the home is crafted for ultimate comfort and entertainment. Prepare gourmet meals effortlessly in the chef’s kitchen and caterer-ready butler’s pantry, or gather at the indoor dining tables and breakfast bar with seating for up to 22 guests. Unwind at the intimate piano bar, enjoy high-speed fiber internet and whole-house SONOS audio throughout, or retreat to the home theater—a state-of-the-art media room seating up to 14 guests for movie nights or the big game. For added accessibility and convenience when moving luggage, the main house includes a private elevator. ***Sleeping Arrangements*** (Sleeps 24 guests total, 18 adults max) The 5-bedroom Great House sleeps 10 adults max, plus 2-4 children in bunk beds. -- Bedroom 1: primary suite, upper-level, king bed, oceanfront, vaulted ceilings, walk-out access to a furnished shared balcony, cable SmartTV, walk-in closet, ensuite with double vanity, beauty counter, and shower. -- Bedroom 2: upper-level, king bed, oceanfront, walk-out access to a furnished shared balcony, SmartTV, ensuite with shower. -- Bedroom 3: upper-level, king bed, oceanfront, walk-out access to a furnished shared balcony, SmartTV, ensuite with shower. -- Bedroom 4: upper-level, 2 sets of full-over-full bunk beds, ocean view, walk-out access to a private balcony, SmartTV, ensuite with double vanity, and shower bath. -- Bedroom 5: upper-level, 2 twin beds, ocean view, walk-out access to a private balcony, SmartTV, ensuite with double vanity, and shower; twin beds can be fitted into a king upon request. -- Bedroom 6: detached exterior suite with private entry, king bed, walk-out access under the west veranda, Smart TV, ensuite with double vanity, and shower. -- Bedroom 7: detached exterior suite with private entry, king bed, walk-out access under the east veranda, Smart TV, ensuite with double vanity, and shower. -- Bedroom 8: guest cottage with private entry, king bed, SmartTV, ensuite with shower. -- Bedroom 9: guest cottage with private entry, 2 twin beds, SmartTV, ensuite with shower; twin beds can be fitted into a king upon request. -- Additional bedding - queen sleeper sofa in the guest cottage living area for 2 children only. Rip Kai is remote enough to be private, but also convenient to local restaurants, beach bars, and water sports. Private transport options are available for restaurant dinners in the eastern districts. Access to our private fitness center is only 15 minutes away for active guests. NOTES: Bicycle and kayak rentals are available at discounted rates. A signed waiver is required. ===> RATE DETAILS <=== -- 13% Occupancy Tax added to all rates. -- 12.90% Service Fee is added to all rates. -- 3.50% Admin Fee added to all rates. -- A Departure Cleaning Fee is added to all rates. ==> BOOKING RULES <=== -- Guests must be 25 years or older to book and must occupy the unit during the entire stay. -- Check-in: 4:00 pm. -- Check-out: 10:00 am. ===> NEARBY POINTS OF INTEREST <=== -- 2 miles to Bioluminescent Bay and the Rum Point Club for food + drink, snorkeling, charter excursions, and water sport rentals. -- 2.5 miles to the Kaibo Beach Bar & Grill and Starfish Point -- 2.8 miles to the nearest general store, Chisholm’s Grocery -- 4.7 miles to Over the Edge restaurant -- 7.2 miles from our Grand Cayman Villas & Condos Welcome Center -- 11 miles to the nearest supermarket, Foster’s Market -- 13 miles to Tukka East restaurant. -- 24.5 miles (45 min drive) from Owen Roberts Airport (GCM) ==> GETTING AROUND <== A rental car is highly recommended. Taxi cabs are unreliable and expensive outside of town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. For rental cars, we recommend Budget Cayman, Avis, Marshalls, or Hertz. ==> BEACH NOTES <== All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. 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.

Cayman Sands

Old Man Bay, KY
5 Bedrooms 14 Guests
Aug 21 - 26
$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. ***IMPORTANT NOTES*** -- A Cleaning Fee may be required due to enhanced cleaning, sanitation, and inspection protocols. -- Additional tandem kayaks available for discounted rental. Signed waiver required. ***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*** -- 5-night minimum stay required. -- 6 nights minimum and full occupancy required over Thanksgiving week. -- 7-night minimum stay and full occupancy rate required over Christmas and New Year’s week -- 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 Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. Should sargassum be extremely heavy behind your property, we will reach out to the owner for alternative solutions which may include a partial refund or relocation. We try our best to work around mother nature.

Coconut Beach

Rum Point, KY
6 Bedrooms 12 Guests
Aug 21 - 26
$1,029 night

***Property Overview*** Coconut Beach is an oceanfront family-friendly oasis located in the picturesque Rum Point community along Grand Cayman’s north coast. This large, one-story beach house spans 4,200 sq. ft. and can sleep 12 guests across 5 bedrooms in the main house, plus a detached 1 bed/1 bath studio suite above the garage. Perfect for vacationing grandparents or in-laws, the studio suite provides added privacy and is never rented out to unrelated guests during your stay. The focal point of the main house is the great room. Connecting both bedroom wings of the villa, and opening onto an enclosed sun porch, the great room provides sunny ocean views throughout the living, dining, and kitchen areas. With its airy, open concept design the great room includes a dining table with seating for 10, a TV den with two cozy couches, and a full kitchen with breakfast counter seating for 6. A separate kids’ table with chairs is provided for our tiny guests. *** Sleeping Arrangements *** (Sleeps 12 guests total) -- Bedroom 1: king bed, ocean views, ensuite with dual vanities and shower. -- Bedroom 2: queen bed, shares Jack & Jill bathroom equipped with a shower. -- Bedroom 3: 2 twin beds, shares Jack & Jill bathroom equipped with a shower; twin beds can be fitted into a king bed upon request. -- Bedroom 4: primary suite, king bed, ocean views, home office with desk + chair, ensuite with shower. -- Bedroom 5: 2 twin beds, ensuite half bath, uses full bathroom off the dining area equipped with a shower bath; twin beds can be fitted into a king bed upon request. -- Bedroom 6: detached apartment suite above the garage, queen bed, full kitchen, HD TV, full bathroom, air conditioning, washer & dryer. Outside, guests at Coconut Beach will enjoy the villa’s sandy, palm-shaded beach, great for long walks, or lazy afternoons with your toes in the sand. The villa’s wraparound patio leads to a new beach cabana with ample seating for sunset viewings. The pool deck is furnished with multiple loungers surrounding the villa’s freshwater plunge pool. An outdoor shower sits off the pool deck to rinse off after a long day of sun and surf. *** Coconut Beach’s Unique Features *** Outdoors: -- Located on a wide lot with lush landscaping, guests will feel they’ve been whisked away to their own enchanted garden by the sea. -- Newly expanded beach cabana with Adirondack chairs and patio seating. -- 2 beach hammocks for afternoon naps by the sea. -- Excellent snorkeling just steps from the backdoor! A healthy marine habitat awaits beneath the waves, we recommend pool shoes or fins for foot protection. -- Freshwater plunge pool with plenty of loungers around the pool deck. Indoors: -- Great beach house vibe with an open concept great room providing plenty of room for the entire family. -- Large flat-screen TV and comfortable sofas for a movie night after a day of sun and surf. -- Full kitchen with modern appliances and plenty of counter space. -- Enclosed sun porch with sofas and Adirondack chairs to enjoy the ocean views. ***IMPORTANT NOTES*** -- A Cleaning Fee may be required due to enhanced cleaning, sanitation, and inspection protocols. -- Additional kayaks are available for discounted rental. Signed waiver required. ***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*** -- 5 nights minimum stay required. -- 6 nights minimum and full occupancy required over Thanksgiving week. -- 7 nights minimum and full occupancy rate required over Christmas and New Year’s week. -- 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 ***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 same day -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- Complimentary pack-n-plays, booster seats, & baby gates -- Kayaks available for discounted rental* *Signed waiver required. =================== ***Villa Cleaning & Sanitation*** -- All villas are cleaned and sanitized prior to each guest’s arrival. We also ask our owners to provide a starter supply of extra cleaning products. -- Additional housekeeping services can be purchased after booking in 3-hour time blocks. Scheduling may be coordinated with your property manager upon arrival. ***Beach Notes*** All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, the beach or water entry behind your property may vary slightly from the images displayed due to shifting weather and tide patterns. The next-door beach is also always available for your use. We advise guests to wear foot protection (pool socks or aqua shoes) when entering the ocean to avoid injury on coral heads, ironshore, or rocks. ***Ocean Debris & Sargassum Seaweed*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that has increased in frequency in recent years. Although sargassum is an unsightly nuisance, it is largely seasonal in summer. Our owners do make efforts to remove heavy sargassum and will have the beach raked prior to your arrival. 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.

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, ensuite bath, 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. 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-Bedroom 3-Bathroom Beachfront Condo with Heated Pool

North Side, North Side, KY
3 Bedrooms 6 Guests
Feb 6 - 12
$525 night

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

Olympus Villa

Rum Point, KY
5 Bedrooms 12 Guests
Aug 26 - 31
$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.

Halcyon Point

Old Man Bay, KY
5 Bedrooms 10 Guests
Aug 21 - 25
$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.

Spacious 3 Bd Beachfront Ground Flr Condo w/ Pool

North Side, North Side, KY
3 Bedrooms 6 Guests
Aug 21 - 26
$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.

White Cottage

East End, KY
5 Bedrooms 11 Guests
Aug 30 - Sep 4
$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.

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

North Side, North Side, KY
3 Bedrooms 6 Guests
Aug 21 - 24
$298 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

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 Front, # 4 Green, Stunning Views

North Side, Grand Cayman, KY
3 Bedrooms 8 Guests
Aug 21 - 23
$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.

Vacation Rentals in North Side by Amenities & Features

Get to Know North Side

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

North Side FAQs

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

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