Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$2,429 - $13,571 /night
Coco
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The splendid luxury vacation villa Coco is located on the heights of Lorient in Saint Barths and offers a spectacular sunset vista, as well as panoramic views over Lorient Bay and the nearby islands. It is very private and elegant, bright and uncluttered:... more
$2,429 - $15,000 /night
Belle Etoile
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Tucked into the hills of the lovely and pristine area of Dévé, the magnificent luxury villa Belle Étoile is a contemporary and stylish vacation rental property in St-Barths, with a 28-meter pool overlooking a breathtaking panoramic view. With its 5 bed... more
$2,429 - $17,143 /night
Ginger
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Located at the top of the private Domaine des Pairs in Petite Saline, the magnificent vacation rental Ginger offers a breathtaking and panoramic view over the islands of St. Martin, Anguilla, Saba, and the islets of Fourchue and Bonhomme. This five-bedroo... more
$2,429 - $9,286 /night
Floating Garden
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The prestigious holiday rental villa Floating Garden welcomes you in the Lurin area for an unforgettable stay in St Barths. In front of a splendid view over the ocean and the glorious sunsets, this three-bedroom vacation rental is the ideal place for a st... more
$2,428 - $4,714 /night
CliffHouse
4 Bedroom Apartment, 5 Bathrooms, Sleeps 8
CliffHouse is located in lower Peter Bay, a gated neighborhood on the North shore of St. John. It is 12,000SF and sits on 3 acres directly next to the National Park for ultimate privacy. At 100 feet up from the shoreline you can hear the waves crashing on... more
$2,428 - $6,400 /night
Sunset
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted rate (plus a 15% service charge). Gu... more
$2,420 - $6,500 /night
Landmark
6 Bedroom House, 7 Bathrooms, Sleeps 12
Nearby construction may result in noise disturbances. For further details on how this might affect your stay, please reach out to a villa specialist.
Landmark House is one of only three villas situated directly on the exclusive Sandy L... more
$2,400 - $9,000 /night
Shiloh Estate
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Shiloh Estate, a luxurious four-bedroom Anguilla villa rental, is nestled within the lush landscapes of Aurora Anguilla Resort & Golf Club. Situated in Anguilla's exclusive West End in Rendezvous Bay, this stunning estate combines pristine white architect... more
$2,400 - $6,900 /night
Sugar Hill
8 Bedroom Villa, 8 Bathrooms, Sleeps 16
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted rate (plus a 15% service charge). Gu... more
$2,363 - $6,300 /night
Hyde Park
6 Bedroom Villa, 9 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted rate (plus a 15% service charge). Gu... more
$2,357 - $8,571 /night
Amandara
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Nestled on the picturesque island of Saint Martin in the Caribbean, Amandara stands as a testament to luxury, elegance, and tranquility. This magnificent 5-bedroom villa is a paradisiacal haven that offers an unparalleled experience of tropical living. Fr... more
$2,357 - $5,143 /night
Keela Wee
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
Located on a private coral cove, this pretty yellow stone villa overlooks one of Jamaica's loveliest bodies of water, Discovery Bay. On its own private coral cove, this property can be rented alone, or in combination with its neighboring sister villa – ... more