Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$1,750 - $5,000 /night
Old Trees 102 | Firefly
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Firefly at Old Trees is a five-bedroom beachfront holiday villa in Barbados. This luxury home sits privately in the Old Trees development on the Platinum Coast of the island. This lateral apartment covers an entire floor and features magnificent views ove... more
$1,750 - $3,150 /night
Villa Calypso
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Villa Calypso takes oceanfront vacationing to a new level. Ideally situated on Ocean Point, it is just a short stroll to Taylor Bay Beach, one of Providenciales' best-kept secrets. This spectacular vacation home is a beautiful example of traditional islan... more
$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 bedroom luxury residence on the Sand... more
$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 - $9,000 /night
Bonnie
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The villa rental Bonnie is a beautiful three-bedroom property overlooking the bay of St-Jean. With its luxurious amenities, bright living spaces and sparkling pool, this vacation rental in St. Barths offers an exceptional setting for a dream vacation for ... 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 - $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