Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$745 - $1,695 /night
Kailypso
3 Bedroom Villa, 2 Bathrooms, Sleeps 8
Welcome to Kailypso, a 3-bedroom beachfront villa in Cayman Kai located on Bio Bay.
Measuring over 2,800 square feet with spectacular outdoor spaces, cozy interiors, and a secluded beach, this popular villa is the perfect destination for family vacatio... more
$743 - $2,858 /night
Just in Paradise
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Nestled in a lush tropical setting, Villa Just in Paradise lives up to its name. From the moment you arrive, you are surrounded by the soft fragrances of jasmine and vibrant bougainvillea entwined around majestic palm trees. The covered entrance, graceful... more
$743 - $4,764 /night
Estrela
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The newly built Villa Estrela is indeed a rising star on the island of St. Barth. Constructed in a traditional Caribbean style, with warm mahogany-toned wood for the pitched ceilings, the luxury rental home is a haven for families, as all four of the bedr... more
$743 - $2,350 /night
Bahia Blue
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Villa Bahia Blue offers an elevated Caribbean escape, surrounded by lush tropical greenery and spectacular views. Set across several levels, this elegant four-bedroom villa combines contemporary comfort, generous outdoor spaces, and a beautifully designed... more
$743 - $2,214 /night
Legacy Villa
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$740 - $3,325 /night
Vista Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Vista is an idyllic, luxury four-bedroom contemporary villa superbly located on the waterfront, offering magnificent views of neighbouring St Martin in the distance, seemingly at the touch of the hand, but for the turquoise, crystal azure water which sepa... more
$740 - $2,775 /night
Sea Winds Villa
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Seawinds is a beautifully designed Caribbean-style waterfront villa sitting in almost an acre of tropical gardens. Located on the seafront, it nestles behind a protective reef which forms the ecologically important Little Harbour. The sea views across the... more
$735 - $1,720 /night
Waverly One
3 Bedroom Villa, 2 Bathrooms, Sleeps 6
Nearby construction may result in noise disturbances. For further details on how this might affect your stay, please reach out to a Rental Escapes villa specialist.
The beach experiences seasonal fluctuations in its accessibili... more
$735 - $1,720 /night
Waverly House
3 Bedroom Villa, 2 Bathrooms, Sleeps 6
Nearby construction may result in noise disturbances. For further details on how this might affect your stay, please reach out to a villa specialist.
Please note: The beach experiences seasonal fluctuations in its accessibility.
Loc... more
$729 - $1,943 /night
Loblolly
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
Make your next Caribbean getaway an unforgettable experience in this luxurious rental villa steps from one of the most exquisite white sand beaches in the British Virgin Islands. Situated on the lush hillside, Loblolly is equally enchanting for guests sea... more
$720 - $2,500 /night
Villa Amber
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The villa has a beautiful wrap-around terrace that offers a breathtaking view of the sea and the island, making it an ideal setting for a relaxing and peaceful vacation.
The villa is set on 2.5 acres of private grounds and gardens, offering guests plen... more
$715 - $1,886 /night
Nid D'Amour
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Nid D’Amour is a breathtaking villa perched on a cliff with impeccable views all around the home, no matter the angle. True to its French translation of “Love Nest,” the drive up towards the property immediately introduces the spectacular ambiance o... more