Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$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.
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$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
$1,500 - $2,395 /night
The Vacation Haven
4 Bedroom Villa, 5 Bathrooms, Sleeps 12
The Vacation Haven is a magnificent luxury villa located in the beautiful hills of the historic landmark Rose Hall, Montego Bay, Jamaica.
It is in a private gated community, adjacent to the beautiful Rose Hall Golf Course and only 10 minutes away from... more
$1,500 - $3,500 /night
Arrecife 48
5 Bedroom Villa, 6 Bathrooms, Sleeps 12
Guests staying within Puntacana Resort & Club will have access to some resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restaurants ($), bars ($) and tennis cen... more
$1,500 - $3,700 /night
Hacienda A33 | Reino
5 Bedroom Villa, 6 Bathrooms, Sleeps 12
Guests staying within Puntacana Resort & Club will have access to some resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restaurants ($), bars ($) and tennis cen... more
$1,500 - $6,050 /night
Sandy Shore
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Sandy Shore is a serene oceanfront escape in the quiet Turtle Tail area of Turks and Caicos Islands. Set on a scenic slice of land with a tranquil lake on one side and the endless turquoise horizon on the other, the villa captures uninterrupted views stre... more
$1,500 - $5,714 /night
Endeavour
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The charming holiday rental Endeavour is located on the heights of Toiny in the heart of a beautiful environment. With a breathtaking view over the Petit-Cul-de-Sac lagoon and the neighbouring hills, and nestled at the end of a road, this idyllic luxury r... more
$1,500 - $4,000 /night
Grand Outlook Villa
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Perched on one of Anguilla's highest points, Grand Outlook is a sanctuary of peace and luxury within a secure gated compound. It offers a retreat where tranquility and rejuvenation meet under the island's brilliant blue skies. This luxury villa rental is ... more
$1,500 - $2,600 /night
Rocksteady Villa
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Rocksteady Villa is a four-bedroom villa that features a 180-degree view of the ocean. You'll need to do nothing but relax as this villa offers chef service, a butler, housekeeping, and a groundsman. Inside you'll find two king bedrooms that open up onto ... more
$1,500 - $3,600 /night
Beach Cake
2 Bedroom Villa, 3 Bathrooms, Sleeps 4
A small, perfectly formed beach retreat filled with quirky features and arty vibes. Located directly on the beach at Turtle Cove and a short walk from the marina, Beach Cake is an intimate retreat where the inside is outside, the downstairs is upstairs, a... more
$1,500 - $6,000 /night
Avanti
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Tucked within the exclusive enclave of Terres Basses, Villa Avanti is a masterpiece of modern Caribbean luxury. A five-bedroom sanctuary designed for privacy, sophistication, and seamless indoor-outdoor living. From the moment you pass through the gated e... more