Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$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 rate (plus a 15% service charge). Gu... more
$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 two bedrooms on the lower level and ... more
$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 rate (plus a 15% service charge). Gu... more
$1,729 - $4,857 /night
La Salamandre
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
La Salamandre is a breathtaking villa nestled in the exclusive Terres Basses region of St. Martin, offering an unparalleled luxury retreat. This exquisite property combines opulent living spaces with stunning natural surroundings, making it the perfect de... more
$1,725 - $3,150 /night
Boathouse 2 BDM
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), ensuring that when the sea beckons, your b... more
$1,714 - $5,143 /night
Privilège Villa
7 Bedroom Villa, 8 Bathrooms, Sleeps 14
Villa Privilege is a hidden gem in the exclusive enclave of Anse Marcel, a serene and picturesque bay overlooking the neighboring island of Anguilla. Nestled within a lush green oasis, this breathtaking retreat offers the perfect blend of tranquility and ... more
$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 seeking privacy, relaxation, and r... more
$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 to modernity and luxury. This 6-bedr... more
$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, located in the serene Indigo Bay of Si... more
$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 for a dream six-people stay in St-Ba... more
$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 for an unforgettable stay in the Cari... more
$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 to the heyday of carefree St. Bart... more