Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$795 - $1,065 /night
Mai Tai Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
A beautiful 4 bedroom private, beachfront villa with amazing views, cool sea breeze and the relaxing sound of the waves touching the sand.
Mai Tai is one of the handful of villas in Silver Sands that provides full-time, first-class service with a train... more
$795 - $1,950 /night
Waves Villa
3 Bedroom Villa, 3 Bathrooms, Sleeps 7
Waves gracefully stands as an illumination of tranquility in the heart of Anguilla, presenting guests with an unparalleled panorama of the illustrious Shoal Bay East, renowned as one of the island's most pristine beaches. This secluded haven marries the q... more
$795 - $2,150 /night
Cayman Sands Villa
5 Bedroom Villa, 5 Bathrooms, Sleeps 12
Cayman Sands is an oceanfront villa in Old Man Bay along the north coast. With an open, one-story design, Cayman Sands offers guests an intimate experience across 4,000 sq ft. of living space, plus a one-bedroom detached guest cottage.
The main house f... more
$795 - $1,995 /night
Hidden Cove
6 Bedroom Villa, 5 Bathrooms, Sleeps 12
Hidden Cove offers a large family, or two smaller families, a home away from home with the amenities of a vacation resort. With a boat dock directly on a secluded cove, guests can launch kayaks, six come provided complimentary, for a day of exploring abov... more
$795 - $1,700 /night
Reeds House Penthouse 14
3 Bedroom Penthouse, 3 Bathrooms, Sleeps 6
Nearby beach construction may result in noise disturbances. For further details on how this might affect your stay, please reach out to a villa specialist.
Reeds House is ideally situated directly on the white sandy beaches of Reeds ... more
$795 - $2,295 /night
Kai Cove
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Kai Cove is a newly renovated beachfront home within the exclusive Cayman Kai area near Rum Point. Blending beach house vibes with Balinese decor, Kai Cove's redesign has been profiled in Real Life Caribbean, a luxury lifestyle magazine.
This stunning... more
$795 - $2,195 /night
Tarasand
4 Bedroom Villa, 3 Bathrooms, Sleeps 8
Welcome to Tarasand! This two-story luxury villa sits on the waterfront in Cayman Kai, a short distance from the Rum Point Club along the north coast. Tarasand is a great family villa offering barefoot swimming off the shores of the home's palm-shaded bea... more
$793 - $2,223 /night
Windsong Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$790 - $999 /night
Moonshine
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
A beautiful four-bedroom villa which opens out onto a lovely wooden deck with an infinity pool overlooking panoramic views of the Caribbean Sea.
One of Jamaica's most beautiful beaches, Silver Sands Beach is only a few minutes walk or a quick butler-dr... more
$787 - $3,429 /night
Bikini
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Located in the Lorient area, famous for its surf spot, the vacation rental Bikini is a three-bedroom property with a splendid ocean view. Comfortable and very well equipped, this vacation rental welcomes a group of friends or a family in the heart of lush... more
$786 - $2,000 /night
Les Palmiers
2 Bedroom Villa, 3 Bathrooms, Sleeps 4
Although it is not directly on the beach, Villa Les Palmiers is in many ways the quintessential beach house. Relaxed, modern, and organic in style, the luxury rental property evokes that same serenity, effortlessness, and warmth of a day by the seashore. ... more
$786 - $2,714 /night
Grand Bleu
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
A vibrant blue gate sets the stage for mesmerizing sea views, photogenic sunsets, unique water features, and stylish tropical living straight out of a design magazine. Entering through the courtyard, a pebbled tropical stream flows invitingly around the u... more