Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$1,515 - $3,057 /night
Vittoria
6 Bedroom Villa, 5 Bathrooms, Sleeps 12
Ideally situated on the southern coastline of Dutch St. Maarten, Villa Vittoria is an exquisite beachfront retreat gracing the pristine white sands of Simpson Bay. With its sweeping Caribbean Sea views and elegant Italian-inspired design, this six-bedroom... more
$1,513 /night
Chateau Genesis Villa
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Château Genesis, located on the unspoiled island of Anguilla in the British West Indies, is one of the newest villas for rent in Anguilla. This gracious three-bedroom oasis is inspired by Caribbean architecture yet provides the best of today’s modern a... more
$1,500 - $3,000 /night
The Fairway
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Royal Westmoreland is one of the Caribbean's finest luxury golf communities. With the Full Membership included in this villa, guests will have access to the gym, unlimited golf ($), driving range ($), tennis courts, Club House, beach facilities at... more
$1,500 - $1,750 /night
Tortuga C15
5 Bedroom Apartment, 6 Bathrooms, Sleeps 10
Guests staying within Puntacana Resort & Club will have access to some resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restaurants ($), bars ($) and tennis cen... more
$1,500 - $3,000 /night
Pebble
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
Located on the secluded East Coast of Barbados, Pebble is a beachfront, holiday villa that blends with the earth itself, bearing all the perfect imperfections of the rugged, windswept side of Barbados. Designed by Sophie Domenge and inspired by the sculpt... more
$1,500 /night
Villa L'Optimiste
4 Bedroom Apartment, 4 Bathrooms, Sleeps 12
Four bedroom luxury villa rental. Introducing the epitome of luxury coastal living, nestled within the prestigious gated beachfront resort of Sea Horse Ranch. Villa l’Optimiste is a two-story, expansive residence with four bedrooms, four bathrooms, a sw... more
$1,500 /night
Villa Diana
4 Bedroom Apartment, 5 Bathrooms, Sleeps 8
Villa Diana is a luxury vacation villa with exquisite space and location. This four bedroom luxury Caribbean property is a classic beach villa with beautiful architecture, an open floor plan, and harmonious interiors embodying both sophistication and rela... more
$1,500 - $4,714 /night
Beau Rivage
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
Beau Rivage, an exclusive retreat nestled along the pristine shores of Baie Rouge Beach in St Martin. Baie Rouge Beach, nearly a mile of soft sand, is a tranquil and naturally beautiful gem. This idyllic property is enveloped by its stunning beach and tro... more
$1,500 - $3,338 /night
Abacus Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Guests of Abacus Villa receive complimentary access to the Rose Hall Club. Benefits include discounted green fees at Cinnamon Hill and White Witch Golf Courses. Cart and caddie fees are separate. Caddies are mandatory (gratuity is not included). T... more
$1,500 /night
Villa Valesta
6 Bedroom Apartment, 5 Bathrooms, Sleeps 12
A luxury beachfront villa in Cabarete, Dominican Republic. Designed for family retreats, pickleball getaways and corporate offsites—with the space, privacy and support to help everyone relax together.
... more
$1,500 - $5,500 /night
Tortuga H6 | Rosana
5 Bedroom Apartment, 7 Bathrooms, Sleeps 12
Guests staying within Puntacana Resort & Club will have access to some resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restaurants ($), bars ($) and tennis cen... more
$1,500 - $2,500 /night
Segura Villa
5 Bedroom Apartment, 6 Bathrooms, Sleeps 10
Segura takes luxury to new levels. A modern interior layout and polished concrete floors grace the entire villa, including the large kitchen with a custom-made dining room table and indoor entertaining and dining areas. Set on three levels, the top of Seg... more