Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$1,750 - $5,000 /night
Arrecife 69 | Allegra
6 Bedroom Villa, 7 Bathrooms, Sleeps 14
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,750 - $5,500 /night
Halle Rose
6 Bedroom Villa, 5 Bathrooms, Sleeps 12
Halle Rose is located within the prestigious Sandy Lane Estate. Guests have access to Clubhouse facilities, beach chairs, cushions, umbrellas and tennis courts.
Located on West Ridge Road, arguably ... more
Additional Fees: Security Deposit $2500.00 flat
Taxes: 12.5%
Taxes: 12.5%
$1,750 - $4,000 /night
Arrecife 55
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
Arrecife 55, a true gem within the esteemed Puntacana Resort & Club, stands as a paragon of luxury living. This highly coveted villa, renowned for its stunning views of the Caribbean Sea and the La Cana Golf Course, prom... more
Additional Fees: Security Deposit $2000.00 flat
Taxes: 18%
Taxes: 18%
$1,750 - $4,500 /night
Amberley House
6 Bedroom Villa, 5 Bathrooms, Sleeps 12
Guests staying within the world-famous Sandy Lane Estate will have complimentary access to all Clubhouse facilities including beach chairs, umbrellas and tennis courts.
Amberley House is a grand six b... more
Additional Fees: Security Deposit $2500.00 flat
Taxes: 12.5%
Taxes: 12.5%
$1,749 - $5,091 /night
Reef House
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,740 - $4,980 /night
Crystal Waters
6 Bedroom Villa, 5 Bathrooms, Sleeps 12
Tranquil nights, clear waters, and sunny beachfront living await at this fabulous island retreat.
Spanning 5,200 sq. ft., Crystal Waters sits directly oceanfront on a 200-foot wide barefoot beach in Cayman Kai. With t... more
Additional Fees: Departure Cleaning Fee $275.00 flat, Damage Waiver $299.00 flat, Cleaning | Damage Deposit $2500.00 flat
Taxes: 30.9%
Taxes: 30.9%
$1,738 - $5,583 /night
Anticipation
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,725 - $3,150 /night
Boathouse Two Bedroom
2 Bedroom Villa, 3 Bathrooms, Sleeps 4
Styled around a close-knit, village-like community aesthetic, the Boat Houses at South Bank are strategically positioned along the marina waterfront. Each offers a private dock (accommodating up to a 26′ boat), ensurin... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 27%
Taxes: 27%
$1,720 - $4,670 /night
Pool House
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
The Pool House Villa offers a spacious living environment in an enviable location. Built to a high specification, the villa was completed. The interiors feature polished hardwood floors and Balinese-style cathedral ceili... more
Additional Fees: Damage Waiver $299.00 flat
$1,718 - $4,851 /night
Round House
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,714 - $6,429 /night
Casa Aquila
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Casa Aquila offers the ultimate beachfront escape on the pristine shores of Baie Rouge, Terres Basses. This luxurious villa seamlessly blends contemporary elegance with laid-back island living, creating a haven for those... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,714 - $5,000 /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%
$1,714 - $5,000 /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%
$1,714 - $9,286 /night
Amis du Vent
3 Bedroom Villa, 5 Bathrooms, Sleeps 6
Villa Amis du Vent is a beautiful three-bedroom property with a heated swimming pool, ideally located in the private Mont-jean neighbourhood. Its breathtaking ocean views and upscale amenities make it the perfect place f... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,714 - $8,571 /night
Rock
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Located on the heights of Lorient, the sumptuous Rock welcomes guests in the heart of a lush tropical environment. Close to the beach and the renowned surf spot, this three-bedroom vacation rental is the perfect place fo... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,714 - $3,450 /night
Sugar Magnolia
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,714 - $9,286 /night
Gustavia Views
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Villa Gustavia Views more than delivers on the promise that is made in its name. The luxury rental property, which has recently been renovated and become available for short-term stays, transports its guests back in time... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,714 /night
Elle
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Located in the charming Pointe Milou neighbourhood, the luxurious rental villa Elle is a recently renovated property with a pop of decoration and colourful statues. Built into the cliffside, this contemporary vacation ho... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,714 - $3,571 /night
Acai
3 Bedroom Villa, 2 Bathrooms, Sleeps 6
Located a few minutes from the white sand beach of Flamands, the luxurious villa Acai offers an outstanding view of the ocean, the beach and the surrounding islands. Built over three levels in a traditional colonial styl... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,714 - $5,429 /night
Casa Cervo
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Nearby construction may result in noise disturbances. For further details on how this might affect your stay, please reach out to a villa specialist.
Set in a tropical courtyard with a circular drive,... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,714 - $4,000 /night
Mapai
6 Bedroom Villa, 6 Bathrooms, Sleeps 14
Villa Mapai is a stunning six-bedroom villa located in the gated community of Terrasse de Cul de Sac. Situated in a picturesque oceanfront setting, the villa offers a luxurious and tranquil escape. Its prime location pro... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,714 - $6,857 /night
Lagon Jaune
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Located in Petit-Cul-de-Sac, the luxurious villa Lagon Jaune is a true haven of peace facing a breathtaking panorama. This four-bedroom vacation home is perfect for a large family or a group of friends travelling togethe... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,714 - $8,571 /night
Krystel
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Located in the hills of Lurin, the luxurious rental villa Krystel is a recent property that offers a breathtaking panoramic view over the bay of St.Jean and the surrounding hills. This four-bedroom vacation home is the p... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,714 - $5,714 /night
Ella
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
Located midway between St. Jean and the village of Lorient, Villa Ella looks out over a sweeping view of blue sky and shimmering sea that will stay in your memory long after your visit has ended. Designed by an owner/arc... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,714 - $8,571 /night
la Danse du Soleil
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Nestled on the heights of Vitet in the private neighbourhood of Dévé, the rental villa La Danse du Soleil is a superb new property with a spectacular panoramic view over Toiny Bay and the entire wild coast of the islan... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,714 - $10,000 /night
Sasha
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
The vacation rental villa Sasha is a sumptuous property located in Corossol with a splendid view over the ocean and the surrounding hills. Built in a modern style on three levels, its privileged location in the heart of ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,714 - $3,143 /night
Casa Rosada
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Welcome to Casa Rosada, your Caribbean vacation home.
Casa Rosada is an architectural gem, perched on a hill overlooking picturesque Chalk Sound, capturing the cross breeze between the sound and ocean. As you look out... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12%
Taxes: 12%
$1,714 - $4,000 /night
Abby
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Abby is situated on the hillside of Vitet on a 32200 ft² plot next to a naturally preserved area. The view of the ocean, the islands and the lagoon is gorgeous. This spacious villa is very private. The open living and t... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,714 - $7,143 /night
Aurea
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Aurea is situated on the top of Lorient. Extremely private, it gets a lot of sunlight and an amazing view on the ocean, from Lorient Bay and the islands of Saint Martin and Anguilla.
A large living room opens onto the... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,714 - $4,571 /night
Casa Tigre
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Looking out from a hillside in Vitet, the luxurious vacation rental property Casa Tigre opens onto a wide vista over the clear waters of the Atlantic Ocean, the Caribbean Sea, and the bay of Grand-Cul-de-Sac. This cozy f... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%