Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$1,964 - $5,176 /night
Sugar Bay
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
On its own sugary white sand beach lapped by the turquoise waters of Discovery Bay sits the exquisite home Sugar Bay. Interiors have just been refreshed throughout and are distinguished by elegant custom-designed furniture, gleaming breadnut floors, and f... more
$1,960 - $4,460 /night
Mullins Mill
8 Bedroom House, 9 Bathrooms, Sleeps 16
Located on eight acres of landscaped grounds, Mullins Mill is a distinctive villa exuding unparalleled charm. Embracing its history, the main house intertwines modern comfort with the heritage of a 17th-century sugar mill, ensuring absolute seclusion acro... more
$1,950 - $10,950 /night
Rip Kai
9 Bedroom Villa, 11 Bathrooms, Sleeps 24
A luxurious gated and walled ocean estate, available in either a 7-bedroom or 5-bedroom configuration, with a deep array of home technology, resort-like amenities, and optional staffing options gives Rip Kai a micro-resort feel.
A convenient oceanfront... more
$1,950 - $5,000 /night
Hacienda B15 | Casa Calma
5 Bedroom Villa, 6 Bathrooms, Sleeps 12
Construction is taking place nearby and may create some noise issues. Contact a Rental Escapes villa specialist for more information about how this may impact your stay.
Guests staying within Puntacana Resort & Club will have a... more
$1,950 - $9,400 /night
Villa Skyline
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Welcome to this serene hillside villa in one of the most beautiful places on the island.
Villa Skyline is a unique hideaway, resting atop Blue Mountain with breathtaking lookouts across the island and the ocean. Like the other villas, it is also eleg... more
$1,950 - $7,143 /night
Villa Tamarind
6 Bedroom Villa, 7 Bathrooms, Sleeps 14
Tamarind Villa is a luxurious six-bedroom villa located directly on the beach at Smith’s Reef, western Grace Bay Beach. Each grand bedroom features an ensuite bathroom, and master suites have private balconies.
Extensive indoor and outdoor dining opt... more
$1,950 - $4,950 /night
Champagne Shores
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
This luxury villa in Anguilla promises to be one of the destinations you'll want to visit time and again. Designed to highlight its oceanfront location, it offers an indoor and outdoor living experience like no other. Whether you want to host your dream w... more
$1,950 - $6,750 /night
Evolution
7 Bedroom Villa, 8 Bathrooms, Sleeps 18
Welcome to Evolution, an oceanfront paradise with picture-perfect panoramic views of Grand Cayman's south coast.
Located mid-island, our guests are only 20-25 minutes away from the airport and Seven Mile Beach, the same distance to Rum Point, and 20 mi... more
$1,950 - $2,497 /night
Luxury Pool Junior Suite
1 Bedroom Apartment, 1 Bathrooms, Sleeps 2
Ideal for romantic getaways, the Luxury Pool Junior Suites, each with airy vaulted ceilings, overlook our lush gardens or magical lagoon.
Have a couples massage in your personal spa area, relax under the pergola in your private courtyard, cool down in ... more
$1,950 - $4,200 /night
Saramanda
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Guests staying within the world-famous Sandy Lane Estate will have complimentary access to all Clubhouse facilities including beach chairs, umbrellas and tennis courts.
Nestled in the exclusive Sandy Lane Estate, Saramanda is a disting... more
$1,950 - $8,950 /night
Sun Salutations
6 Bedroom Villa, 6 Bathrooms, Sleeps 18
Embark on an unparalleled five-star luxury vacation experience at Sun Salutations, an exquisite oceanfront estate in the posh Cayman Kai neighborhood.
This home seamlessly blends minimalist design with a tranquil ambiance and resort-like amenities, off... more
$1,929 - $9,286 /night
Esprit De Roche
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Villa Esprit De Roche is a sumptuous three-bedroom property with a swimming pool located on a hillside in Colombier. Facing the amazing show of the glorious sunsets over the ocean, this vacation rental offers wide spaces in a paradise setting. In St-Barth... more