Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$2,000 - $2,500 /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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$2,000 - $3,428 /night
BougainVilla on Spring Farm
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Guests of BougainVilla on Spring Farm 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 n... more
$2,000 - $11,429 /night
Casa Minotto
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The luxury rental villa Casa Minotto is a very private paradise in the heart of the island of St-Barts, with a beautiful view of the ocean in the distance. Located in Pointe-Milou, this contemporary villa built on several bungalows welcomes you for an int... more
$2,000 - $8,143 /night
White Sun
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The luxurious villa White Sun is the perfect combination of luxury, calm and beauty. Located on a hillside in Petite Saline, this outstanding rental home in St. Barth is fully air-conditioned and offers a range of high-quality services in a new, refined a... more
$2,000 - $6,600 /night
Round Rock Estate
6 Bedroom Villa, 9 Bathrooms, Sleeps 12
Round Rock Estate is a contemporary six-bedroom villa on the idyllic island of Anguilla. Completely renovated in 2019, no expense was spared to make the most of the breathtaking waterfront location. Located in a quiet part of the island, activities and di... more
$2,000 - $3,428 /night
Villa Rosa
5 Bedroom Villa, 7 Bathrooms, Sleeps 10
Guests of Villa Rosa 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). Tee... more
$2,000 - $6,500 /night
Limin' Da Coconut
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
Limin’ Da Coconut is a stunning modern villa perched above Anguilla’s Little Harbour, set on a secluded stretch of coastline with turquoise waters and breathtaking blue skies, perfect for those seeking luxury villas.
The grand modern entrance, ador... more
$2,000 - $8,571 /night
la Danse du Soleil
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Nestled on the heights of Vitet in the private neighbourhood of Dévé, the rental villa La Danse du Soleil is a superb new property with a spectacular panoramic view over Toiny Bay and the entire wild coast of the island of St.Barths.
Spread over five... more
$2,000 - $4,000 /night
Sunrise Villa
8 Bedroom Villa, 8 Bathrooms, Sleeps 16
Sunrise Villa is a private beachfront villa rental that offers five acres of 400 feet of beachfront in the exclusive gated neighborhood of Orchid Bay Estates, Cabrera, Dominican Republic. Sunrise Villa has over 11,000 square feet comprised of eight bedroo... more
$2,000 - $5,000 /night
Cielo
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$2,000 - $12,500 /night
Aliseo at Sandy Lane
9 Bedroom Villa, 11 Bathrooms, Sleeps 18
Guests staying within the world-famous Sandy Lane Estate will have complimentary access to all Clubhouse facilities including beach chairs, umbrellas and tennis courts.
Discover this stunning tropical villa featuring 9 en-suite bedro... more
$2,000 - $5,143 /night
Tichka
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Villa Tichka will captivate you! It is perfectly located above Flamands beach, facing the sunset. Not too near the beautiful beach, just enough to give you privacy, but at a stone's throw distance to go down the stairs in the garden from the beach.
Fr... more