Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$2,000 - $4,643 /night
Cielo
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $2500.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,000 - $12,500 /night
Aliseo at Sandy Lane
9 Bedroom Villa, 9 Bathrooms, Sleeps 18
Guests staying within the world-famous Sandy Lane Estate will have complimentary access to all Clubhouse facilities including beach chairs, umbrellas and tennis courts.
Discover this stunning tropic... more
Additional Fees: Security Deposit $2500.00 flat
Taxes: 12.5%
Taxes: 12.5%
$1,999 - $5,999 /night
Tortuga C17
7 Bedroom Apartment, 8 Bathrooms, Sleeps 14
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,995 - $3,121 /night
Sea Palms
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Guests of Sea Palms villa are greeted by a paradise-like setting. The main house features a bright and airy great room with multiple areas for sitting and entertaining. The space has cool tile floors and high, wood-beam ... more
Additional Fees: Security Deposit $299.00 flat
Taxes: 27%
Taxes: 27%
$1,995 - $4,995 /night
Villa Mora
7 Bedroom Villa, 8 Bathrooms, Sleeps 17
Welcome to Villa Mora. This luxurious 7-bedroom 7.5-bath gated ocean estate sits on over 200 feet of beachfront with fabulous snorkeling and breathtaking sunset views of tranquil South Sound.
Spanning over 8,000 sq. ... more
Additional Fees: Departure Cleaning Fee $295.00 flat, Damage Waiver $299.00 flat
Taxes: 30.9%
Taxes: 30.9%
$1,986 - $4,400 /night
Ma Moura
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$1,971 /night
Oasis Palms
5 Bedroom Apartment, 5 Bathrooms, Sleeps 10
strong>Nestled in the exclusive community of Cap Cana is Eden Roc, a luxury beach resort along the Caribbean Sea. Guests will have access to all Eden Roc resort facilities including a lagoon-style swimming pool, restaura... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,971 - $5,114 /night
Tichka
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
It is perfectly located above Flamands beach of facing the sunset …
Not too near the beautiful beach, just enough to give you a privacy, but at a feet distance to go down the stairs in stone in the garden from the bea... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,964 - $5,175 /night
Sugar Bay
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
On its own sugary white sand beach lapped by the turquoise waters of Discovery Bay sits the exquisite home Sugar Bay. Interiors have just been refreshed throughout and are distinguished by elegant custom-designed furnitu... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,950 - $10,950 /night
Rip Kai
9 Bedroom Villa, 11 Bathrooms, Sleeps 24
A luxurious gated and walled ocean estate, available in either a 7-bedroom or 5-bedroom configuration, with a deep array of home technology, resort-like amenities, and optional staffing options gives Rip Kai a micro-reso... more
Additional Fees: Departure Cleaning Fee $595.00 flat, Damage Waiver $299.00 flat
Taxes: 34.4%
Taxes: 34.4%
$1,950 - $5,000 /night
Hacienda B15 | Casa Calma
5 Bedroom Villa, 6 Bathrooms, Sleeps 12
Construction is taking place nearby and may create some noise issues. Contact a Rental Escapes villa specialist for more information about how this may impact your stay.
Guests staying within ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,950 - $9,400 /night
Villa Skyline
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Welcome to this serene hillside villa in one of the most beautiful places on the island.
Villa Skyline is a unique hideaway, resting atop Blue Mountain with breathtaking lookouts across the island and the ocean. Lik... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 22%
Taxes: 22%
$1,950 - $7,143 /night
Villa Tamarind
6 Bedroom Villa, 7 Bathrooms, Sleeps 14
Tamarind Villa is a luxurious six-bedroom villa located directly on the beach at Smith’s Reef, western Grace Bay Beach. Each grand bedroom features an ensuite bathroom, and master suites have private balconies.
Exte... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12%
Taxes: 12%
$1,950 - $4,950 /night
Champagne Shores
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
This luxury villa in Anguilla promises to be one of the destinations you'll want to visit time and again. Designed to highlight its oceanfront location, it offers an indoor and outdoor living experience like no other. Wh... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 23%
Taxes: 23%
$1,950 - $6,750 /night
Evolution
7 Bedroom Villa, 8 Bathrooms, Sleeps 18
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 sa... more
Additional Fees: Departure Cleaning Fee $495.00 flat, Damage Waiver $299.00 flat
Taxes: 30.9%
Taxes: 30.9%
$1,950 - $4,200 /night
Saramanda
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Guests staying within the world-famous Sandy Lane Estate will have complimentary access to all Clubhouse facilities including beach chairs, umbrellas and tennis courts.
Nestled in the exclusive Sandy ... more
Additional Fees: Security Deposit $2500.00 flat
Taxes: 12.5%
Taxes: 12.5%
$1,950 - $8,450 /night
Sun Salutations
6 Bedroom Villa, 6 Bathrooms, Sleeps 18
Embark on an unparalleled five-star luxury vacation experience at Sun Salutations, an exquisite oceanfront estate in the posh Cayman Kai neighborhood.
This home seamlessly blends minimalist design with a tranquil ambi... more
Additional Fees: Departure Cleaning Fee $395.00 flat, Damage Waiver $299.00 flat, Cleaning | Damage Deposit $2500.00 flat
Taxes: 34.4%
Taxes: 34.4%
$1,929 - $6,000 /night
Aqua Dream
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Discover Villa Aqua Dream: Your gateway to unrivalled luxury in St. Maarten.
Nestled in the picturesque coastal enclave of Indigo Bay on the captivating island of Sint Maarten, Villa Aqua Dream stands as a testament t... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,929 - $6,000 /night
Aqua Vista
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Nestled harmoniously alongside its sister property, Aqua Vista is a modern masterpiece in its own right, offering an unparalleled fusion of contemporary elegance and island luxury. This magnificent six-bedroom villa, loc... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,929 - $9,286 /night
Esprit De Roche
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Villa Esprit De Roche is a sumptuous three-bedroom property with a swimming pool located on a hillside in Colombier. Facing the amazing show of the glorious sunsets over the ocean, this vacation rental offers wide spaces... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,921 - $5,410 /night
Sweet Spot
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
Located on a wide sandy beach, Sweet Spot is like a pretty jewel box next to the sea. Its remarkable location is the best of all worlds. A 6,000-square-foot private home with a huge lawn and beach.
Interiors at Sweet ... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,920 - $7,200 /night
Sunset Corail
1 Bedroom Villa, 1 Bathrooms, Sleeps 2
Sunset Corail is a Caribbean-designed villa located on the Gypsea Beach Club property, in the popular Saint Jean neighbourhood.
The villa features a living room with a fully equipped kitchen opening onto a terrace wit... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,920 - $4,500 /night
Tortuga C19 | Good Vibes
8 Bedroom Villa, 9 Bathrooms, Sleeps 16
Construction is taking place nearby and may create some noise issues. Contact a Rental Escapes villa specialist for more information about how this may impact your stay.
Guests staying within ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,914 - $9,286 /night
Tourmaline
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Villa Tourmaline is a splendid three-bedroom property ideally located in Grand-Cul-de-Sac, facing the crystal-clear waters of the lagoon. Along with villas Larimar, Lazuli, and Quartz, these four properties form a luxuri... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,914 - $9,286 /night
Quartz
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Villa Quartz is a sumptuous vacation rental in St-Barths, offering a breathtaking view over Grand-Cul-de-Sac. Spacious and bright, this three-bedroom property with a heated pool offers upscale amenities in a peaceful and... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,914 - $10,714 /night
Lazuli
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Lazuli is a luxurious four-bedroom vacation rental with a heated swimming pool, ideally located facing the Grand-Cul-de-Sac lagoon. Boasting an exceptional location, this spacious and bright holiday rental welcomes up to... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,914 - $10,714 /night
Larimar
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Villa Larimar is a sumptuous four-bedroom property facing the crystal-clear waters of Grand-Cul-de-Sac lagoon. Enjoying a privileged location, this prestigious vacation rental offers bright spaces in a most refined setti... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,900 - $5,170 /night
Leeward Jewel Villa
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
Leeward Jewel Villa is a stunning luxury villa with a private pool located on the breathtaking island of Providenciales in the Turks and Caicos Islands. This exclusive retreat offers an unparalleled experience of serenit... more
Additional Fees: Damage Waiver $299.00 flat, Cleaning Fee $1000.00 flat
Taxes: 12%
Taxes: 12%
$1,900 - $4,200 /night
Twin Palms Villas
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Twin Palms Villas is undoubtedly one of Anguilla’s most conveniently situated vacation homes. For larger parties, a two-bedroom Beach Palm Villa can be combined with a three-bedroom Coconut Palm Villa to create a spaci... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 23%
Taxes: 23%
$1,900 - $4,500 /night
Cool Wind
6 Bedroom Villa, 6 Bathrooms, Sleeps 14
The Fairmont Royal Pavilion is one of the most prestigious resorts in Barbados. Guests will have complimentary access to the Pavilion Beach Club and restaurants ($).
Cool Wind has a show-stopping, e... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12.5%
Taxes: 12.5%
$1,900 - $4,800 /night
La Villa Salee
6 Bedroom Villa, 6 Bathrooms, Sleeps 14
Stay in style and luxury at our six-bedroom villa on the Dutch side, perched on St. Maarten’s Pelican peninsula, surrounded by stunning mountains and ocean views of the Caribbean and the Atlantic. (The Villa also has a... more
Additional Fees: Security Deposit $5000.00 flat
Taxes: 10%
Taxes: 10%
$1,900 - $5,000 /night
The Cottage At Meads Bay
3 Bedroom Cottage, 4 Bathrooms, Sleeps 6
The Cottage at Meads Bay is an ideal beachfront villa in Anguilla situated right on the vibrant coastline of northwest Anguilla’s renowned Meads Bay. This iconic locale is celebrated for its luxurious ambiance and brea... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 23%
Taxes: 23%
$1,900 - $5,000 /night
Arrecife 53 | Mandala
6 Bedroom Villa, 7 Bathrooms, Sleeps 14
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,900 - $5,567 /night
Villa Lolita
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$1,895 - $2,595 /night
Villa Coquina
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Being just steps away from Dawn Beach, you'll enjoy the mesmerizing ocean views from the Beachfront Villa. Luxury furnishings throughout the villa will make you feel pampered, happy, and relaxed, especially as you enjoy ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 20%
Taxes: 20%
$1,886 - $9,429 /night
Hill House
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Located on the heights of Camaruche in Lorient, villa Hill House is a lovely property facing a breathtaking ocean view. Spacious and bright, this four-bedroom vacation home offers the finest amenities in a lush environme... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,875 /night
Las Canas 50
4 Bedroom Apartment, 5 Bathrooms, Sleeps 10
All guests must register with the Casa de Campo Concierge office, and for a small daily fee ($30 per adult per night & $15 per child per night), are granted access to resort areas and amenities. Casa de Campo Res... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 8%
Taxes: 8%
$1,875 - $3,000 /night
Calabash Penthouse
1 Bedroom Villa, 1 Bathrooms, Sleeps 2
Calabash Luxury Boutique Hotel & Spa combines five-star service and luxury within a relaxed and intimate environment to create the ultimate Caribbean escape.
The Penthouse Suite is our signature suite at the Calabash,... more
Additional Fees: Damage Waiver $299.00 flat
$1,872 - $6,000 /night
Hacienda B18 | Escondida
5 Bedroom Apartment, 7 Bathrooms, Sleeps 14
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Security Deposit $3000.00 flat
Taxes: 18%
Taxes: 18%
$1,870 - $2,200 /night
Leamington House
5 Bedroom House, 5 Bathrooms, Sleeps 10
Leamington House is a colonial style great house set in the exclusive Leamington Estate. Extended by the famous architect, Oliver Messel, the house was for many years the home of the American Ambassador.
It was recent... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12.5%
Taxes: 12.5%
$1,860 - $5,000 /night
Tortuga C12 | Atalaya
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,860 - $4,580 /night
Arrecife SB5 | 3 Palmeras
6 Bedroom Villa, 7 Bathrooms, Sleeps 14
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,860 - $4,580 /night
Arrecife EFG4 | Yellow Bear
6 Bedroom Villa, 6 Bathrooms, Sleeps 14
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,857 - $9,571 /night
Nala
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
This rental villa in St. Barths Nala is a beautiful property nestled on a hill above Grand-Cul-de-Sac. This five-bedroom vacation rental is located only a few steps from the beach and water activities, a perfect place fo... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,857 - $10,000 /night
Reef Point
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Nestled on a hillside at the quietest and farthest end of St.Jean Bay, the luxurious rental villa Reef Point is a superb property located in a private and very quiet domain. Built on a single level, Reef Point offers one... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,857 - $6,429 /night
D'Zir
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Located in Colombier, the luxury vacation villa D'Zir is a recent property that offers a breathtaking view of the Caribbean Sea and the port of Gustavia. This architectural gem and sun-soaked paradise is the ideal home f... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,857 - $7,143 /night
Cairn
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Located in the private development of Domaine du Levant in Petit-Cul-de-Sac, the vacation rental Cairn is a superb modern property facing a stunning view over the bay of Petit-Cul-de-Sac and the beach. With four spacious... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,857 - $10,000 /night
Alhena
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
Alhéna is situated in Lurin. Very private, it offers a stunning view on Saint Jean bay. The large living and the kitchen open onto the terrace and the long pool. The decoration is contemporary and comfortable. One bedro... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,857 - $4,571 /night
Vista del Mar
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$1,857 - $12,857 /night
Senna
5 Bedroom Villa, 6 Bathrooms, Sleeps 12
Villa SENNA is a stunning five-bedroom property with a swimming pool, ideally located in St-Jean. Nestled in the lush environment of St-Barths, this vacation home accommodates up to twelve guests in bright, airy spaces. ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%