Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$1,050 - $3,000 /night
Jaguey 3
4 Bedroom Villa, 6 Bathrooms, Sleeps 8
Jaguey 3, a stunning 4-bedroom villa, epitomizes the essence of Caribbean elegance. Nestled in the heart of the Arrecife community within the prestigious Puntacana Resort & Club, this property offers breathtaking views of the La Cana Golf Course. A stone'... more
$1,050 - $4,150 /night
Roc E Mar
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Villa Roc E Mar is a sumptuous property located in Toiny on Saint-Barths’ wild coast. The landscapes that surround this modern-architecture vacation rental make a unique atmosphere for a most luxurious stay listening to the sound of the ocean waves. Con... more
$1,050 - $2,800 /night
High Spirits
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Royal Westmoreland is one of the Caribbean's finest luxury golf communities. With the Social Membership included in this villa, guests will have access to the gym ($), golf course ($), tennis courts ($), Club House ($), beach facilities at Mullins... more
$1,050 - $2,985 /night
Beaulieu
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Perched above the shimmering turquoise waters of the Caribbean Sea, Villa Beaulieu offers an extraordinary vantage point over Baie Rouge Beach, with uninterrupted views stretching toward the neighboring island of Anguilla. This exclusive single-level vill... more
$1,045 /night
Oceanfront Grand Studio
1 Bedroom Hotel, 1 Bathrooms, Sleeps 2
Located within a stunning oceanfront building that showcases breathtaking beach views, this spacious 670 square foot retreat provides a luxurious king bed or two cozy queen beds (separate room categories), an elegantly designed bathroom with a shower and ... more
$1,043 - $2,038 /night
2 BDM Lanai Bungalow at Windsong Resort
2 Bedroom Bungalow, 2 Bathrooms, Sleeps 4
This 2 2-bedroom lanai Bungalow has a spacious, 625 sq. ft. private lanai -- perfect for outdoor entertaining. Accessed via sliding glass doors from the living room and master bedroom, the lanai features a BBQ grill, dining level fire pit and verdant land... more
$1,039 /night
Tortuga Paradise
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restaurants ($), bars ($) and tennis cent... more
$1,039 /night
Tropical Zen Escape
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Set along the picturesque Caribbean Sea is La Cana Beach Club. Guests have access to all Club facilities including the swimming pool, lounge chairs, showers, tables and chairs, restaurant ($) and bar ($).
Guests staying within ... more
$1,029 - $5,429 /night
Ocean's 21
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Ocean’s 21 is a magnificent 4-bedroom villa located in the quiet district of Petit Cul de Sac. With beautiful sea views, it offers an idyllic setting for a peaceful, relaxing stay with family or friends.
The villa’s interior design is both soft and... more
$1,029 - $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
$1,029 - $2,886 /night
Paradiso
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
Situated in the lush green hills of Sint Maarten in the exclusive area of Oyster Pond Estates is Paradiso, a six-bedroom, six-and-a-half bath villa. It is truly a gem of a villa. The minute you walk through the magnificent front doors, the astounding pano... more
$1,024 - $2,763 /night
No Problem
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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