Large group vacation rentals in Breakers, Cayman Islands

Explore 288 large group vacation rentals, homes, and villas in Breakers for your next getaway or business trip. With space for everyone, enjoy the comfort and privacy of a home designed for gathering, alongside premium amenities such as Air Condition Homes, Homes with Pools and Homes with Free Parking. Throughout your stay, spend time together, share meals, and relax in spacious living areas that make group travel feel cohesive. With options starting as low as $30 per night and homes offering up to 12 bedrooms and 14 bathrooms, it's easy to book a stay that fits your group. And with 24/7 local support and high-speed Wi-Fi, everyone stays connected and protected. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, making each trip more rewarding than the last. Book your next group getaway with Homes & Villas by Marriott.

288 Great for Groups in Breakers

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.

Hidden Treasure & Guesthouse

East End, KY
6 Bedrooms 18 Guests
Aug 23 - 28
$913 night

***Property Overview*** Welcome to Hidden Treasure + Little Treasure, centrally located on the quiet southern coast. With over 5,500 sq. ft., this stately oceanfront villa features a private infinity pool, beach fire pit, spacious interiors, and a screened dining balcony. This 6-bedroom beachfront villa sits on over 100 feet of sandy beach and iron shore with convenient backyard snorkeling and breathtaking sunrise views. A newly installed private dock + hammock cabana provide gentle water entry or simply lounging above the waves. The main villa can sleep 12 guests across five spacious bedrooms, three of which are oceanfront. The 1-bedroom guest house sleeps an additional 2 adults, plus 2 small children on a sleeper sofa. The gourmet kitchen features modern appliances, granite countertops, and breakfast bar seating for four. The formal dining area provides seating for 10. The screened dining balcony seats 12 for meals with sweeping ocean views. Hire a chef for a night of gourmet dining or start your day with brunch service on the dining balcony. This listing includes both the 5-bedroom villa and 1-bedroom guest house sleeping 18 guests total or 16 adults max. ***Sleeping Arrangements*** (Sleeps 18 guests total, 14 adults max) -- Bedroom 1: lower-level, queen bed, ocean views, walk-out access to the pool deck, closet, ensuite bath with soaking tub, and separate shower. -- Bedroom 2: primary suite, upper-level, king bed, ocean views, walk-out access to a shared oceanfront balcony, television, closet, office with desk + chair, ensuite with dual vanity, soaking tub, and separate shower. -- Bedroom 3: upper-level, queen bed, ocean views, walk-out access to a shared oceanfront balcony, closet, desk + chair, shares a jack-and-jill bathroom with shower bath. -- Bedroom 4: upper-level, two twin beds, closet, shares a jack-and-jill bathroom with shower bath. -- Bedroom 5: upper-level, four twin-over-twin bunks + two trundle beds, closet, and ensuite with shower. -- Bedroom 6: full bed, garden views, television, ensuite with shower bath; sleeper sofa in the living room. ***Hidden Treasure’s Notable Features*** -- High-speed fiber optic internet for streaming devices and work-from-home professionals. -- Air-conditioned throughout. -- Home office on the second floor with workstation, private balcony, and oversized recliner. There is no sleeping option in the office. -- Propane grill for island cookouts. -- Propane fire pit for late-night hangouts on the beach. -- Dock with hammock cabana for gentle water entry or siestas above the waves. Daily housekeeping is optional and can be arranged for guests in addition to a private chef, massage therapist, personal trainer, or yoga instructor. Hidden Treasure is conveniently located 30 minutes east of the airport. The villa is only 15 minutes from the supermarket, 10 minutes from Ocean Frontiers, one of Cayman’s premier dive operators and 5 minutes from both our private fitness center and Cayman Health City. ***IMPORTANT NOTES*** -- A Cleaning Fee is included due to enhanced cleaning and sanitation protocols. -- Tandem or single kayaks are available for discounted rental. A signed waiver is required. ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service Fee added to all rates. -- Accidental Damage Protection added to all rates. ***Booking Rules*** -- Christmas & New Year’s are split into two rental periods. Please inquire about your travel dates before booking. -- 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 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 -- Tandem kayaks available for discounted rental* *Signed waiver required. =============== ***Nearby Points of Interest*** -- 33 minutes from Owen Roberts Int’l Airport (GCM) -- 4 minutes from our Welcome Center -- 5 minutes to The Blowholes -- 10 minutes to La Casita restaurant and Ocean Frontiers Dive Shop -- 13 minutes to Tukka East restaurant and the Cayman Parrot Sanctuary -- 15 minutes to The Italian Kitchen restaurant and Tortuga Divers -- 17 minutes to the nearest supermarket, Foster’s Countryside -- 18 minutes to Spotts Public Beach -- 19 minutes to the Rum Point Club -- 22 minutes to the Kaibo Beach Bar & Grill and Starfish Point -- 35 minutes to Seven Mile Beach ***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. All 3 have pickup locations at the airport. ***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. ***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 is largely seasonal in summer months. Our owners do make efforts to remove heavy sargassum and will have the beach raked before 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. ***Beach Notes*** The entire island is only 22 miles wide from west to east, so you are never too far from anywhere on Grand Cayman. The villas in the Cottage District on the southeast coast offer great reef-protected snorkeling with calm waters plus proximity to the island’s best dive operators--Ocean Frontiers and Tortuga Divers. 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.

Wind Upon The Waves

East End, KY
3 Bedrooms 8 Guests
Aug 30 - Sep 4
$1,259 night

***Property Overview*** Welcome to Wind Upon the Waves, a newly built, single-level home on the island’s South Coast. The owners have designed this 5,000-square-foot gated residence for privacy and exceptional panoramic views of the south coast. For travelers seeking ample living space, home technology, and a contemporary design, Wind Upon The Waves checks all the boxes. Being only 5 minutes from Cayman Health City makes this home a convenient home base for patients seeking cardiac, orthopedic, or stem-cell treatments nearby. The single-level design also makes this villa wheelchair-accessible. The open-concept great room is the central focal point of the home with modern furniture, a formal dining table, and a dreamy gourmet kitchen. The vaulted ceilings dramatically accentuate the space while allowing natural light to fill the room. In-ceiling speakers with Sonos audio keep the vibe going throughout the great room, primary suite, fitness room, and outdoor lanai. Multiple walls of glass windows and doors frame the stunning ocean views from virtually every angle while providing convenient walk-out access to the pool deck. A formal dining table with seating for 8 separates the living area from the gourmet kitchen. Top-of-the-line kitchen appliances are perfect for hiring a private chef or pre-stocking the home with your choice of groceries and beverages. A propane grill and outdoor dining table sit on the pool deck for alfresco sunset dinners. All three bedrooms are oceanfront suites with private attached bathrooms, televisions, and walk-out access to the pool deck. ***Sleeping Arrangements*** (Licensed to sleep 6 adults max, 8 guests total.) -- Primary Suite - king bed, oceanfront, television, walk-out access to the pool deck, ensuite bath with dual vanity, water closet, and walk-in oceanview shower with rainfall shower head. -- West Suite - queen bed, oceanfront, television, walk-out access to the pool deck, ensuite bath with walk-in shower. -- Middle Suite - two twin beds, oceanfront, television, walk-out access to the pool deck, ensuite bath with shower/tub combo. Twin beds can be fitted into a king bed upon request. -- Additional sleeping - queen sleeper sofa in the media room, television, walk-out access to the pool deck, shares hall full bathroom with shower. The villa enjoys fiber-optic internet for streaming devices and remote professionals. The media room, adjacent to the middle suite, comes equipped with a large television and a surround sound audio system perfect for sporting events or family movie nights. Adjacent to the primary suite, the fitness room is a workout paradise with ocean views and the following equipment: -- Freemotion Dual Cable Cross Lite Machine -- Concept2 Rower + Schwinn Airdyne AD7 Bike -- Kettlebells + Dumbbells + Fixed Barbells -- Flat & Adjustable Bench -- Medicine + Bosu + Exercise balls -- Ab Roller + Resistance Bands -- Agility Ladder -- Battle + Jump Rope -- Exercise Mat + Stretching Strap + Yoga Block -- Due to liability concerns, the barbell, plate weights, and treadmill are not available to guests. For the adventurous, the best SCUBA diving can be found in the East End. Meaning you’re only 15 minutes away from some of the best dive sites and operators in the Caribbean. Take the plunge and cross some amazing dives off your bucket list! ============ ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 12.90% Villa Concierge & Service Fee is added to all rates. -- A Departure Cleaning Fee is added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays may be available but are 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. -- 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 *Signed waiver required. ***Beach Notes*** Wind Upon the Waves sits on an elevated, iron-shore shelf overlooking the Caribbean Sea. The villa has a sandy backyard beachfront; however, you cannot enter the ocean from the back of the home. Jagged rocks and rough tides make water entry here perilous. Instead, guests should visit nearby Heritage Beach or Colliers Public Beach. 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 seaweed 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.

Blue Serenity

North Side, KY
4 Bedrooms 10 Guests
Aug 23 - 28
$914 night

***Property Overview*** Welcome to Blue Serenity, a luxurious 4-bedroom villa on Cayman’s central south coast. Perfect for active families and groups, this villa offers backyard snorkeling, modern amenities, and three new pickleball courts. The owner offers guests access to the pickleball courts from 9:00 a.m. to 5:00 p.m. daily. Paddles and pickle balls are provided upon request only. Blue Serenity has been meticulously upgraded with a new pool deck, enclosed sunroom, redesigned upper-level king suites, and an entirely new lower-level apartment suite. The stunning new pool and multi-level decks are a sunbather’s dream. The pool features a Baja shelf with submerged loungers, ideal for soaking up the sun. A pergola provides some shade, ensuring enjoyment from dawn to dusk. You’ll likely spend more time by the pool and beach than exploring the rest of the island. With plenty of sun loungers and outdoor seating, every guest will have a spot to unwind and relax under the sun. An outdoor shower on the pool’s west end offers a quick rinse before heading inside. Two elevated decks overlook the pool. One deck is furnished with an alfresco dining table, and the other with comfortable lounge seating—perfect for alfresco happy hours or sunset dinners with sweeping ocean views. Blue Serenity features three upper-level bedroom suites and a lower-level apartment suite, all newly renovated with modern furniture and decor. Both levels are included when booking the home. We do not rent out each level individually. ***Sleeping Arrangements*** (Sleeps 10 guests total, 8 adults max.) -- Bedroom 1: primary suite, upper-level, ocean views, king bed, walk-out sun porch, ensuite with dual vanity and shower. -- Bedroom 2: upper-level, ocean views, king bed, walk-out sun porch, ensuite with dual vanity and shower. -- Bedroom 3: upper-level, ocean views, king bed, walk-out sun porch, ensuite bath with dual vanity and shower. -- Bedroom 4: apartment suite, lower-level, private entrance, kitchenette, king bed, uses hall bathroom with shower. -- Additional Bedding: a queen sleeper sofa in the apartment suite, suitable for two children. The upper-level floor plan includes a 60-foot enclosed sunroom with oceanfront windows, a formal dining table, and two sitting areas. The open-concept family room connects the kitchen and living area, ensuring ocean views from every angle. Fenced pickleball courts are across the street. The owner has some paddles and balls to share. The fully equipped kitchen features new cabinets, modern stainless steel appliances, and an island counter with breakfast bar seating for four. Dishes, cookware, glassware, and cutlery are all provided. The living area is perfect for unwinding at the end of the day. Enjoy the HD television and plush sectional sofa for a movie night after a day of fun in the sun. The lower-level apartment suite has a kitchenette, living area, bedroom, bathroom, and a screened breakfast nook with pool deck access. With its luxurious amenities and breathtaking views, Blue Serenity is perfect for family vacations and group getaways. Reserve your stay today and prepare for an unforgettable Cayman escape. NOTES: Kayaks pictured above are not included with the villa. Kayaks can be rented at discounted rates before arrival. 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 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. -- 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 charge 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 Services Discount Card -- 10% advance booking discount for a 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 -- Kayaks available for discounted rental* *Signed waiver required. =================== ***Nearby Attractions*** -- 30 minutes from the airport, Owen Roberts International (GCM) -- 5 minutes from our Grand Cayman Villas & Condos Welcome Center -- 20 minutes to the nearest supermarket, Foster’s Countryside -- 10 minutes to La Casita restaurant -- 15 minutes to Tukka East restaurant and the Cayman Parrot Sanctuary -- 20 minutes to The Italian Kitchen restaurant -- 5 minutes to Heritage Beach -- 5 minutes to The Blowholes -- 20 minutes to Spotts Public Beach -- 20 minutes to Rum Point Beach -- 25 minutes to the Kaibo Beach Bar & Grill and Starfish Point -- 40 minutes to Seven Mile Beach ***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 over the summer months. Our owners will take measures 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

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

North Side, Grand Cayman, KY
2 Bedrooms 4 Guests
Oct 31 - Nov 3
$475 night

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

KiToCay Villa

Old Man Bay, KY
3 Bedrooms 5 Guests
Aug 23 - 28
$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.

Willow Beach

North Side, KY
4 Bedrooms 12 Guests
Aug 23 - 28
$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.

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.

Halcyon Point

Old Man Bay, KY
5 Bedrooms 10 Guests
Aug 23 - 27
$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.

Silver Reef 1 Luxury 2BR Beachfront Retreat with Pool

Old Man Bay, North Side, KY
2 Bedrooms 4 Guests
Aug 24 - 26
$191 night

Welcome to Silver Reef #1, a tranquil ground-floor end unit on Grand Cayman’s North Side. This newly built 2BR/2BA beachfront condo blends modern comfort with soothing ocean views, ideal for guests seeking relaxation, privacy, and a stylish base to explore the island. Within the gated Silver Reef Residences, this corner unit offers abundant natural light, added privacy, easy access to on-site amenities, and a private patio to enjoy sea breezes. Book your stay and experience true North Side calm. Welcome to Silver Reef #1, a peaceful ground-floor end unit tucked along the quiet, natural coastline of Grand Cayman’s North Side. From the moment you arrive, the calm of the sea and the ease of the space invite you to slow down and settle into island life. This newly built two-bedroom, two-bathroom beachfront retreat blends contemporary design with the soothing rhythm of the ocean, ideal for travelers seeking tranquility, open views, and a luxurious home base for exploring Grand Cayman. As part of the intimate, gated Silver Reef Residences, this corner unit offers added privacy, beautiful natural light, and seamless access to the community’s amenities. Inside, the condo unfolds into an airy, open-plan layout crafted for effortless island living. The fully equipped kitchen features European-style cabinetry, quartz countertops, and modern stainless-steel appliances, giving you everything you need to prepare a simple breakfast or a full dinner after a day on the water. The living area flows naturally toward the private patio, where ocean breezes and the sound of the shoreline create the perfect backdrop for coffee at sunrise or a glass of wine at dusk. The bedrooms are designed with relaxation in mind. The primary suite offers a king bed, ample storage, and a spa-inspired en-suite bathroom. The guest bedroom features a queen bed with its own full bathroom just steps away. Plush linens, soft towels, and thoughtful essentials make settling in effortless. As a ground-floor end unit, Silver Reef #1 offers a quieter, more private outdoor experience. Guests can enjoy direct access to the complex’s heated 40’ saltwater pool, complete with a spacious sundeck and shaded cabanas. A short walk brings you to the peaceful, uncrowded coastline of the North Side, perfect for sunbathing, strolling, or simply listening to the waves. The secure gated community and on-site parking add convenience and peace of mind. To help you get settled, we provide a generous starter pack of essentials including dish soap or dishwasher tabs, salt, pepper, and coffee filters. Bathrooms include shampoo, conditioner, hand soap, toilet paper, and fresh towels. Laundry detergent, a blow dryer, an iron and ironing board, high-speed Wi-Fi, cable TV, and beach towels are also provided for your convenience. The entire condo, pool, beach and grounds. 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. To help you enjoy the beautiful ocean right in front of the property, we suggest bringing water shoes for easier and more comfortable entry. There is no cable but guests may log in to their own streaming accounts (Netflix etc.) to watch TV. 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.

Cayman Sands

Old Man Bay, KY
5 Bedrooms 14 Guests
Aug 23 - 28
$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.

Villa Caymanas

North Side, KY
4 Bedrooms 8 Guests
Aug 23 - 28
$633 night

***Property Overview*** Welcome to Villa Caymanas! This beautiful oceanfront villa is located in Old Man Bay along the north coast. Boasting four full king suites, an oceanfront freshwater pool, and an expansive balcony, Villa Caymanas is the perfect vacation retreat. Whether you prefer to explore the snorkeling reefs nearby or simply relax by the pool, it’s all just steps off the back door. The beach here is strictly pebbly (rarely sandy), but the owner has a very sandy backyard around the pool deck. The villa is directly in front of Babylon, one of the top 5 dive sites on the entire island. The snorkeling in this area is excellent; however, fins or pool shoes are necessary to protect your feet. Villa Caymanas’ modern, streamlined architecture features many oversized oceanfront windows that flood the interiors with natural sunlight year-round. The kitchen, living, and dining areas open onto a second-floor balcony spanning the full width of the house, providing stunning ocean views. Guests have the option of dining indoors or al fresco off the balcony. A modern kitchen comes equipped with standard appliances, dishware, cookware, cutlery, and a coffee maker. An exercise room and home office are also on the lower level. Bedroom & Bathroom Layout (Sleeps 8 guests total) -- Bedroom 1: primary suite, upper-level, king bed, ocean views, HD cable TV, walkout access to the balcony, walk-in closet, ensuite with dual vanity and double shower. -- Bedroom 2: upper-level, king bed, garden views, HD cable TV, ensuite with shower. -- Bedroom 3: lower level, king bed, ocean views, HD cable TV, walkout access to the pool deck, ensuite with shower. -- Bedroom 4: lower level, king bed, ocean views, HD cable TV, walkout access to the pool deck, ensuite with shower. With gorgeous views throughout, comfortable furnishings, and wonderful outdoor space, Villa Caymanas is sure to please! NOTES: Bicycles and single/tandem kayaks are available for discounted rental; a signed waiver is required. ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 10% Guest Service added to all rates. -- Accidental Damage Protection added to all rates. -- A Departure Cleaning Fee is added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays are welcome but subject to a higher cleaning fee. Please inquire to book. -- Must be 25 or older to book and must occupy the property during the entire stay. ***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. ***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.

Bella Vista

East End, KY
5 Bedrooms 11 Guests
Aug 23 - 28
$1,029 night

***Property Overview*** Perched high on a dramatic bluff overlooking the deep blue Caribbean Sea, Bella Vista is a breathtaking 5-bedroom, 5.5-bath masterpiece offering unmatched privacy, serenity, and style. With no neighbors on either side, this 5,000-sq-ft villa delivers uninterrupted ocean panoramas from all five king suites—each with its own spa-quality ensuite and stunning sea views. Designed with impeccable craftsmanship and curated décor, Bella Vista is made for travelers who crave elevated indoor–outdoor living. The expansive oceanfront terrace features a heated spa, oversized pool, multiple shaded verandas, and sweeping sunset views—creating the perfect setting for relaxing, gathering, and entertaining. Every detail has been thoughtfully appointed, including luxury linens, boutique toiletries, a wet bar, and full air-conditioning. Inside, a show-stopping great room welcomes you with soaring ceilings and nearly 40 feet of sliding glass that open seamlessly to the pool deck. The gourmet kitchen centers the home with a large island, premium appliances, and seating for up to 14 guests. Plantation shutters and thoughtful finishes add coastal charm, though with such mesmerizing views, most guests never close them. ***Sleeping Arrangements*** (Sleeps 12 guests total) -- Bedroom 1: lower level, oceanfront, king bed, television, walkout access to the pool deck, ensuite with dual vanity, ocean views, soaking bathtub, and separate shower. -- Bedroom 2: lower level, oceanfront, king bed, television, walkout access to the pool deck, ensuite with dual vanity, ocean views, and shower with dual shower heads. -- Bedroom 3: lower level, oceanfront, king bed, walk-out access to the pool deck, ensuite with ocean views, and a shower bath. -- Bedroom 4: primary suite, upper level, oceanfront, king bed, television, walkout access to a private balcony, ensuite with dual vanity, ocean views, soaking bathtub, and separate shower. -- Bedroom 5: upper level, oceanfront, king bed + twin daybed with trundle, ensuite with ocean views, and a shower. Bella Vista is also just a 15-minute drive from our Welcome & Fitness Center on Frank Sound Road—perfect for guests seeking convenience without sacrificing seclusion. Ideal for families and groups who want generous bedroom suites, dramatic views, and total privacy, Bella Vista delivers refined island living at its finest. ***Rate Details*** -- 13% Occupancy Tax added to all rates. -- 12.90% Villa Concierge & Service Fee added to all rates. -- A Departure Cleaning Fee is added to all rates. ***Booking Rules*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire 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. -- Check-in is at 3:00 pm; Check-out is at 10:00 am. ***Grand Cayman Villas & Condos Guest Services*** Your Concierge & Service Fee includes your Guest 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 Services Discount Card for savings at local businesses -- 10% advance booking discount for private charter -- Complimentary use of snorkel equipment -- Guest parcel receipt & hold for check-in -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors, guest services desk assistance -- Airport arrival Fast-Track VIP Process (fee charged by CAA) -- Special event/dinner reservations At-Villa Benefits -- Welcome amenity basket -- Complimentary early check-in, if no check-out on the same day -- Day-after-arrival guest services follow-up -- Hotel-grade bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- $5,000 of Accidental Villa Damage Protection -- Complimentary pack-n-plays, booster seats, & baby gates =================== ***Beach Notes*** Bella Vista has No Beach. All beaches in Grand Cayman are technically public since the Crown owns up to the high watermark. Be advised, Bella Vista is located on the ironshore bluff, so for beach swimming, our guests will usually drive to the famous Rum Point Club, where our guests are welcomed to use the sun loungers, swim in the water, dine and drink, or hire watersports...all with a 10% discount earned by renting with our company. All guests will receive a guest benefit card, accepted at select restaurants and vendors throughout Grand Cayman. ***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. ***Getting Around*** A rental car is recommended. Taxis are everywhere, but fares can get expensive, especially for shuttling around George Town and Seven Mile Beach. Plus, there is no Uber or Lyft on the island. We recommend Budget Cayman (20% discount available after booking), Avis, or Marshalls for rental cars.

Beautiful 3 Bd Beachfront Home North Side Sleeps 7

North Side, Grand Cayman, KY
3 Bedrooms 7 Guests
Aug 29 - Sep 1
$206 night

Welcome to Azure Breeze #6, a recently renovated beachfront property. This stunning 3-bedroom, 2-bathroom home, nestled within a small 6-unit complex, invites you to embark on an unforgettable vacation in the Cayman Islands. Located on the northern coast of Grand Cayman, Azure Breeze offers convenient proximity to Crystal Caves, Rum Point, and Cayman Kai, ensuring access to a variety of exciting adventures. With comfortable accommodations for up to 7 guests, including a king, queen, and a full bed with an overhead single bunk, this spacious two-story retreat is thoughtfully designed for both relaxation and family fun. Step outside onto the secluded beach and sway in a hammock beneath the coconut trees, as gentle sea breezes embrace you. Watch as children joyfully play on the shore or venture into the crystal-clear waters for snorkeling and kayaking adventures. Inside, every detail of this exquisite villa exudes elegance. Revel in breathtaking views from multiple windows, capturing the essence of the coastal paradise. Upstairs, sliding doors invite refreshing breezes and illuminate the main living room, which offers a tranquil space to unwind. The patio on the main floor is perfect for entertainment and relaxation, and features a beachside BBQ area with a provided propane grill. On the ground floor, a cozy bedroom with a queen-sized bed and a bathroom with a shower await. The recently renovated kitchen showcases modern appliances and utensils, ensuring a seamless culinary experience. While Azure Breeze #6 provides a private sanctuary, it remains conveniently close to a local grocery store, attractions, and restaurants, ensuring your needs and desires are effortlessly fulfilled. Indulge in the allure of this coastal oasis, where the pristine beach, stylish accommodations, and proximity to local treasures converge to create an unforgettable vacation experience. To fully embrace the serene ambiance of North Side, we suggest renting a car for convenient transportation, as public options may be limited. With George Town approximately 50 minutes away, having a car will grant you the freedom to explore the area’s hidden treasures and embrace the picturesque beauty at your own leisurely pace. A 2-seater kayak with lifejackets and snorkeling gears are available at the property. 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.

Maravilla

North Side, KY
4 Bedrooms 9 Guests
Aug 23 - 28
$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.

Coastal Charm

North Side, KY
3 Bedrooms 9 Guests
Aug 23 - 28
$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.

Spacious 3 Bd Beachfront Ground Flr Condo w/ Pool

North Side, North Side, KY
3 Bedrooms 6 Guests
Aug 23 - 28
$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.

Great Bluff Estates

Gun Bay, KY
5 Bedrooms 12 Guests
Aug 24 - 29
$1,317 night

***PROPERTY OVERVIEW*** Experience the height of Caribbean luxury at Great Bluff Estates, an oceanside sanctuary perched on the bluffs of Grand Cayman’s tranquil Northside. This gated, five-bedroom villa blends modern luxury with the raw beauty of the East End, offering a secluded retreat for jet-set travelers who seek both privacy and first-class amenities. The heart of the home is a dramatic two-story great room, where vaulted ceilings and expansive glass-railed decks preserve panoramic views of the shimmering sea. The modern living area is designed for seamless entertaining with an HD television and a home sound system, plus an open-concept sunroom that flows directly onto an oceanfront deck. Whether you are hosting a formal dinner for ten or enjoying your morning coffee in the sun-drenched breakfast nook, the gourmet kitchen—fully equipped with high-end appliances, wine chillers, and dedicated beverage stations—is prepared for every occasion. The outdoor experience at Great Bluff Estates is unparalleled, centered around a spacious, elevated pool deck with sweeping ocean views. Here, guests can lounge on plush chaises or gather around the family-style dining table for an al-fresco feast overlooking the Caribbean. The centerpiece of this terrace is the private freshwater pool and a brand-new, six-person heated spa, perfect for stargazing on cool island nights. To ensure ultimate comfort, complimentary pool heat is provided for winter stays. The pool deck also features a covered veranda with a wet bar and a full outdoor bathroom. For those who maintain their wellness routine while traveling, the property features a private home gym located just off the pool deck, complete with cardio machines, free weights, and an HD TV. Each of the five bedroom suites is a masterclass in comfort, particularly the 1,500-square-foot Primary Suite. This sprawling west-wing retreat features a dedicated study, walkout access to the upper-level ocean balcony, and a palatial ensuite. Every detail, from the high-speed fiber optic internet to the attentive local management, is designed to provide a seamless, resort-style experience in the privacy of your own estate. ***Sleeping Arrangements*** (Licensed to Sleep 12 guests total) -- Bedroom 1: primary suite, king bed, upper-level, oceanfront, parlor with sectional sofa and HD cable TV + Apple TV, home office with desk + chair, walk-out access to a furnished ocean balcony, large ensuite with double vanity, soaking tub, and separate shower. -- Bedroom 2: queen bed, upper-level, oceanfront, walk-out access to a furnished ocean balcony, ensuite with shower. -- Bedroom 3: queen bed, upper-level, garden views, ensuite with shower. -- Bedroom 4: queen bed, lower level, garden views, ensuite with shower. -- Bedroom 5: queen bed, lower-level, garden views, shares connected full bath equipped with a shower bath. -- Additional Sleeping: den with queen sleeper sofa, lover-level, ocean views, shares connected full bath equipped with a shower bath. Beyond the pool, the estate’s grounds transition into a multi-tiered paradise. Two meticulously manicured terraces of artificial grass provide additional lounging space just steps from the shore, leading to a thatched cabana furnished with Adirondack chairs and a hammock--the ultimate spot for sunset cocktails. A newly installed concrete path offers effortless access to the water’s edge, where a raked sandy area leads you into some of the island’s most vibrant snorkeling. The remote East End allows you to enjoy the company of spotted eagle rays and sea turtles in total serenity. Great Bluff Estates is conveniently located within 10-15 minutes of restaurants, casual island lunch spots, a small shopping plaza with a supermarket and a wine & spirits distributor, plus two large resorts with manicured beaches, water sports, and gift shops. *Note: Housekeeping can be added to your reservation after booking. **Tandem and single kayaks are available for discounted rental. A signed waiver is required. ====== ***NEARBY ATTRACTIONS*** -- 6.2 miles from Grand Cayman Villas & Condos Welcome Center -- 1.3 miles from Foster’s Morritt’s Express -- 1.4 miles from Italian Kitchen Restaurant -- 3.4 miles from Tukka East -- 3.5 miles from Parrot Sanctuary -- 4.5 miles from the Crystal Caves -- 11.3 miles from Rum Point Club -- 12.3 miles from Kaibo Bar & Grill -- 12.8 miles from Starfish Point -- 23.5 miles (43 min 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 all rates. -- 12.90% Villa Concierge & Service Fee added to all rates. -- A Departure Cleaning Fee is added to all rates. -- Additional tandem kayaks available for discounted rental. Signed waiver required. ***BOOKING RULES*** -- Christmas & New Year’s dates are split into two rental periods. Please inquire about your travel dates before booking. -- Shorter stays may be available but are subject to a higher cleaning fee. Please inquire before booking. -- Must be 25 years or older to book and must occupy the property during the entire stay. -- Check-in is at 3:00 pm -- Check-out is at 10:00 am ***GUEST SERVICES*** The Concierge & Service Fee includes your Guest Services Membership. Member Benefits -- Centralized on-island Guest Services & Welcome Center -- Unlimited use of Private Fitness Center (18+ yrs.) -- Business Center Access: computers, printer, scanner, & FedEx/DHL supplies -- Proprietary Guest benefit & discount card -- 10% advance booking discount for private charter -- Complimentary use of snorkel equipment -- Guest parcel receipt & hold for check-in -- Jacques Scott Wine & Spirits pre-order & hold for check-in -- Referral to preferred vendors, guest services desk assistance -- Airport arrival Fast-Track VIP Process (fee charged by CAA) -- Special event/dinner reservations At-Villa Benefits -- Welcome amenity basket -- Complimentary early check-in, if no check-out on the same day -- Day-after-arrival guest services follow-up -- Gilchrist & Soames bath products -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- $2,500 of Accidental Villa Damage Protection -- Complimentary pack-n-plays, booster seats, & baby gates -- Kayaks available for discounted rental* *Signed waiver required. ============ ***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, 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.

Evolution

Bodden Town, KY
7 Bedrooms 18 Guests
Aug 23 - 28
$2,243 night

*** PROPERTY OVERVIEW *** Welcome to Evolution, an oceanfront paradise with picture-perfect panoramic views of Grand Cayman’s south coast. Located mid-island, our guests are only 20-25 minutes away from the airport and Seven Mile Beach, the same distance to Rum Point, and 20 minutes to the best kite-boarding, wind-surfing, and scuba diving in the East End. Evolution was specifically designed to offer seven large bedroom suites and a massive vaulted great room, all on one floor and each with direct oceanfront views with walk-out access to the pool and spa. This is a great entertaining villa for hosting a large group. There is only one way to design such a villa… so Evolution is quite wide at 165+ feet. Evolution is situated on over 250’ of sandy beach, adjacent to Bodden Town’s cemetery beach. Choose from two primary suites, four queen suites, and a slumber party suite that sleeps 8 across two sets of full-over-full bunks and an Xbox One gaming console. **Sleeping Arrangements** (Sleeps 20 guests; 16 adults max.) -- Bedroom 1: ocean view, king bed, walk-out access to the pool deck, cable television, Apple TV, Sonos audio, room safe, ensuite with dual vanity, water closet, plus soaking tub and shower. -- Bedroom 2: ocean view, queen bed, walk-out access to the pool deck, cable television with Apple TV, Sonos sound system, ensuite with shower. -- Bedroom 3: ocean view, queen bed, walk-out access to the pool deck, cable television with Apple TV, Sonos sound system, ensuite with shower. -- Bedroom 4: ocean view, queen bed, walk-out access to the pool deck, cable television with Apple TV, Sonos sound system, ensuite with shower. -- Bedroom 5: ocean view, two full over full bunks, Xbox One console, walk-out access to the pool deck, cable television, Apple TV, Sonos audio, ensuite with shower bath. -- Bedroom 6: ocean view, queen bed, walk-out access to the pool deck, cable television with Apple TV, Sonos sound system, ensuite bath with shower. -- Bedroom 7: ocean view, king bed, walk-out access to the pool deck, cable television, Apple TV, Sonos audio, room safe, ensuite with dual vanity, water closet, plus soaking tub and shower. **Key Villa Features** -- Oceanfront great room with vaulted ceilings and stunning ocean views. Contemporary sectional sofa, modern decor, plus a large HD cable TV with a Sonos home audio system. -- The formal dining table seats 12 guests; the kitchen island seats another 7. -- Multiple outdoor dining tables and lounge areas. -- Modern kitchen with high-end appliances plus a full complement of dishware, cookware, cutlery, and small appliances. Our private chefs love this kitchen! -- Elevated pool deck with infinity pool and heated spa. -- Access to a members-only Fitness Studio 15 minutes away. -- Complimentary snorkel equipment is provided for all guests upon request. Wander the secluded shoreline and discover what it’s like to have the beach almost to yourself, or rub elbows with islanders at local spots like the Czech-Inn Grill, South Coast, or Grape Tree Café. *Note: All weekly stays receive a mid-stay light cleaning to be scheduled with the property manager upon arrival. **Single and tandem kayaks are available for discounted rental. A signed waiver is required. ===================== *** NEARBY ATTRACTIONS *** -- 0.5 miles to the Czech Inn Grill -- 4.2 miles to the grocery store, Foster’s Countryside -- 5.1 miles to Spotts Beach -- 6.3 miles from our Welcome Center -- 11.2 miles to Smith’s Barcadere -- 13.0 miles to Seven Mile Beach or shopping & dining at Camana Bay. -- 11.5 miles to La Casita and Tukka East -- 11.0 miles (24 min drive) from Owen Roberts Int’l Airport (GCM) -- 16.0 miles to the Rum Point Club, The Kaibo, or 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 Avis, Marshalls, or Hertz. *** 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 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. -- Check-in is at 3:00 pm. -- Check-out is at 10:00 am. *** GUEST SERVICES PERKS *** The Villa Concierge & Service Fee includes your Guest Services Membership. ***Member Benefits*** -- Free snorkel equipment during your stay for all members of your group -- 10% early bird discount towards a private charter to Stingray City -- Guest Benefits Card for 10% discounts at restaurants, watersport rentals, excursions, and more -- Centralized on-island Welcome Center with guest-only gym and business hub -- Business Hub with iMacs, 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 of locally sourced treats -- Free baby gear for us during your stay: pack-n-plays, booster seats, & baby gates -- Complimentary early check-in, if no check-out on the same day -- Day-after-arrival guest services follow-up -- Gilchrist & Soames bath products -- Mid-stay light cleaning for weekly stays only -- Pre-stocking of groceries & beverages (delivery fee applies) -- Arrange chefs, cooks, babysitting & family photography -- $3,000 of Accidental Villa Damage Protection -- Additional single/tandem 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. Please note that the beach or water entry behind your property may vary slightly from the images displayed due to changes in 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. ***SARGASSUM ADVISORY*** Beaches in Grand Cayman may also experience floating ocean debris and sargassum weed seasonally. Sargassum is a generally harmless floating seaweed that peaks 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. We try our best to work around Mother Nature.

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

North Side, North Side, KY
3 Bedrooms 6 Guests
Aug 23 - 26
$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

Timeless Paradise

Rum Point, KY
11 Bedrooms 28 Guests
Aug 23 - 28
$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.

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Vacation Rentals Near Breakers

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