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
$1,725 - $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
$1,720 - $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 ceilings. The villa has a large open gal... 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
$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 home welcomes a large family or sever... more