Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
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MilBrooks Resort Villa
10 Bedroom Villa, 11 Bathrooms, Sleeps 20
Surround yourself with the timeless elegance of Milbrooks Resort, Rose Hall, Jamaica. Located within walking distance of the world-famous Half Moon Golf Course in Montego Bay.
An Exclusively Elegant Boutique Villa, surrounded by lush, green, beautifull... more
$6,000 - $25,000 /night
Bachelor Hall
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
Please note that due to the passage of Hurricane Beryl, this property may have limited beachfront access.
Bachelor Hall in Barbados is an ultra-luxurious 3.4-acre, 7-bedroom estate located on one of the most idyllic West Coast beaches ... more
$6,000 - $15,000 /night
Haystack
10 Bedroom Villa, 10 Bathrooms, Sleeps 20
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$5,999 - $11,999 /night
Juanillo 25
6 Bedroom Apartment, 7 Bathrooms, Sleeps 12
Please note that the Corales Golf Course will be closed to the public from April 14th - April 20th for a PGA event.
Guests staying within Cap Cana will have access to all resort amenities and facilities. Resort amenities and f... more
$5,900 - $16,900 /night
Beach Enclave Long Bay 7 BDM Beachfront Villa
7 Bedroom Villa, 8 Bathrooms, Sleeps 14
Beach Enclave’s signature design is present throughout this 7,800-plus-square-foot, five- bedroom villa. This design ethos features a seamless philosophy of combining indoor and outdoor living spaces with generous, concealable sliding glass doors, an ex... more
$5,900 - $15,700 /night
Portofino
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Designed by Edinburgh, Scotland-based Coast Architects. The Residence will cover 6,500 square feet of indoor and outdoor space, five bedrooms, and five and a half bathrooms, including 2,600 square feet of outdoor space with a private deck, infinity pool, ... more
$5,870 - $8,800 /night
Juanillo 2 | Las Hamacas
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
Guests staying within Cap Cana will have access to all resort amenities and facilities. Resort amenities and facilities include a golf course ($), spa ($), restaurants ($), bars ($), and tennis centre ($).
This marvelous property has... more
$5,810 - $10,000 /night
La Serenissima
8 Bedroom Apartment, 12 Bathrooms, Sleeps 16
Guests staying within Puntacana Resort & Club will have access to some resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restaurants ($), bars ($) and tennis cen... more
$5,800 - $15,500 /night
Beach Enclave Grace Bay 6 BDM Premium Ocean View Villa
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
The ultimate experience at Grace Bay’s most exclusive address, the premium ocean-view villa raises the bar with spacious contemporary design and luxurious amenities. This over-the-top vacation experience provides unparalleled ocean views from nearly eve... more
$5,800 - $20,000 /night
Silver Sands
8 Bedroom Villa, 7 Bathrooms, Sleeps 16
Silver Sands is a villa like no other in the collection. Inspired by its ocean-scape surroundings, the stunning architecture of this home thoughtfully integrates natural stone and wood elements into the home’s contemporary living spaces, allowing guests... more
$5,800 - $30,000 /night
Santosha
8 Bedroom Villa, 10 Bathrooms, Sleeps 18
Santosha Villa Estate offers the ultimate in oceanfront luxury. Originally built as a personal home, Anguilla’s largest private estate is decorated in classic Caribbean décor with custom furnishings, antiques, and art throughout – all set against the... more
$5,780 - $13,890 /night
Hacienda Retreat
9 Bedroom Villa, 10 Bathrooms, Sleeps 18
Wake to gentle ocean breezes and sweeping sunrises over the sea at Hacienda Retreat, an exclusive coastal sanctuary in Cabrera where barefoot luxury meets attentive, personalized service. Every moment—from dining beneath the starlit sky to relaxing in p... more