Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$2,286 - $6,900 /night
Sugar Hill
8 Bedroom Villa, 8 Bathrooms, Sleeps 16
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,286 - $8,325 /night
Following Seas
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $3000.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,286 - $4,000 /night
Golden Clouds
15 Bedroom Estate, 17 Bathrooms, Sleeps 30
Golden Clouds Country Estate is a spectacular waterfront villa located in the picturesque village of Oracabessa.
Fifteen minutes from Ocho Rios, on Jamaica's fabled North Coast and neighboring Ian Fleming’s "Golden... more
Additional Fees: Damage Waiver $299.00 flat
$2,286 - $9,286 /night
Villa K
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Located on the beach of Anse les Cayes, the sumptuous rental Villa K is a very modern property nestled in the heart of coconut trees behind the dune. A true gem designed by the architectural company Patrick Raffeneau, Vi... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$2,280 - $4,000 /night
La Sultana
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
All guests must register with the Villa Owners Club, and for a small daily fee ($25 per adult per night & $12 per child per night), are granted access to resort areas and amenities. Casa de Campo Resort facilitie... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$2,279 - $5,869 /night
Someday Soon
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,277 - $8,400 /night
Love Song Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
As you step into the grand foyer, you are greeted by an open-concept design that invites the mesmerizing sea views to become an integral part of your stay. Floor-to-ceiling windows adorn the living spaces, allowing natur... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 22%
Taxes: 22%
$2,271 - $13,929 /night
Cap Au Vent
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Located at the very tip of Pointe-Milou, the vacation rental villa Cap Au Vent is an emblematic villa in St-Barthelemy with multi-pavilion architecture. Built-in a charming mix of both a Mediterranean and a Caribbean des... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$2,270 - $3,670 /night
Miramar
7 Bedroom Villa, 7 Bathrooms, Sleeps 12
Miramar is a one-of-a-kind luxurious mansion in a private estate perched on a bluff overlooking the Caribbean Sea. The former Appleton Estate, featured in Elite Traveler's 2017 Top Ten Villas in the Caribbean, is a villa... more
Additional Fees: Damage Waiver $299.00 flat, Cleaning Fee $625.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,251 - $6,300 /night
Hyde Park
6 Bedroom Villa, 9 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,250 - $8,000 /night
Onyx
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Please note the beach experiences seasonal fluctuations in its accessibility.
Experience the soulful side of Onyx, a private five-bedroom luxury villa located on one of the most soothing West Coast be... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12.5%
Taxes: 12.5%
$2,250 - $4,490 /night
Premier Oceanfront 3 BDM Suite
3 Bedroom Hotel, 4 Bathrooms, Sleeps 6
The ultimate in luxury and amenities with 3800 square feet of living space, located on the top floor with unsurpassed views of the beach and ocean from 2 balconies, as well as a unique island view from a third balcony. ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 27%
Taxes: 27%
$2,250 - $5,400 /night
Windward
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Guests staying within the world famous Sandy Lane Estate will have complimentary access to all Clubhouse facilities including beach chairs, umbrellas and tennis courts.
Windward - a luxurious two-st... more
Additional Fees: Security Deposit $2500.00 flat
Taxes: 12.5%
Taxes: 12.5%
$2,245 - $3,350 /night
Timbuktu By The Sea
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Timbuktu is a modern, contemporary villa with the most beautiful seafront. The entrance is through handsomely carved doors that lead into the main living area. A covered verandah and dining area lead out to the pool with... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,220 - $4,580 /night
Hacienda A39
7 Bedroom Villa, 8 Bathrooms, Sleeps 16
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$2,217 - $5,487 /night
Sea Glass
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,214 - $7,857 /night
Villa OTT
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The luxury villa OTT in St-Barths is a magnificent four-bedroom property with panoramic views over St-Jean Bay up to Saline. Nestled in the heart of the tropical vegetation, this spacious vacation rental welcomes groups ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$2,214 - $8,571 /night
W View
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Nestled at the top of St. Jean’s hill, the vacation rental villa W View is a sumptuous four-bedroom property with spectacular views over the ocean, the rolling hills and the neighbouring islets. Perfect for a family or... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$2,209 - $6,000 /night
Bougainvillea House
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,205 - $33,134 /night
Whale Point
2 Bedroom Apartment, 3 Bathrooms, Sleeps 4
With uninterrupted views of the sparkling sea, Whale Point is situated on Oil Nut Bay’s dramatic Atlantic Ridge. This ocean view rental on Virgin Gorda’s south shore is an intimate escape, offering simple yet sumptuo... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 28%
Taxes: 28%
$2,205 - $5,235 /night
Sol Mate
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Overhanging the ocean on the southern ridge of Oil Nut Bay, Sol Mate Villa opens up to a full 180-degree view of the Caribbean Sea. As one of our most exclusive two-bedroom British Virgin Islands rentals, it is the epito... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 31%
Taxes: 31%
$2,200 - $7,300 /night
Rehab
6 Bedroom Villa, 5 Bathrooms, Sleeps 12
Serene canal views and inviting decor inside and out make Rehab a tranquil retreat where busy families can disconnect. From sunrise to sunset and beyond, this modern Caribbean property’s palm-shaded outdoor spaces are... more
Additional Fees: Security Deposit $5000.00 flat
Taxes: 22%
Taxes: 22%
$2,200 - $6,000 /night
Fiore
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Villa Fiore is a luxurious four-bedroom retreat offering privacy and elegance in Anguilla. Just a short stroll from the pristine Shoal Bay East, this Anguilla villa rental boasts stunning panoramic views of the crystal-c... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 23%
Taxes: 23%
$2,200 - $6,500 /night
Turquoise Villa
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Chic and contemporary, Turquoise Villa is only steps away from Grace Bay beach. Ideal for family vacations, Turquoise Villa offers an abundance of outdoor space for enjoying the tropical weather, paired with bright and s... more
Additional Fees: Security Deposit $3000.00 flat
Taxes: 22%
Taxes: 22%
$2,200 /night
Villa Coral
9 Bedroom Villa, 9 Bathrooms, Sleeps 18
Welcome to Villa Coral, the most elegant and extravagant villa in Bavaro, Punta Cana.
This U-shaped villa has seven comfortable bedrooms, each with a private bathroom, and an 8th bedroom with two bunk beds (queen bed ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$2,200 - $5,633 /night
Beachfront 2 BDM Suite
2 Bedroom Apartment, 2 Bathrooms, Sleeps 4
Our Beachfront Suites are dynamic, light-filled beachfront apartment radiates a sense of calm that comes from their inimitable spatial equilibrium with stunning ocean and beach view terraces/ balconies, the ambiance exud... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 28%
Taxes: 28%
$2,200 - $8,500 /night
Triton at Kamique
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Villa Triton is located in a secluded cove on the south coast of Anguilla in Lockrum. It offers beautiful views of the Caribbean and is situated on a beach with calm waters, perfect for snorkeling due to the presence of ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 23%
Taxes: 23%
$2,200 - $12,500 /night
Aliseo at Sandy Lane
9 Bedroom Villa, 9 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 tropic... more
Additional Fees: Security Deposit $2500.00 flat
Taxes: 12.5%
Taxes: 12.5%
$2,200 - $10,000 /night
Villa Riviera
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Immerse yourself in elegance and refinement with Villa Riviera, a true gem located in the heart of Terres Basses in an exceptional private residence. Nestled in an unspoilt natural setting, this villa offers an idyllic s... more
Additional Fees: Security Deposit $3000.00 flat
Taxes: 10%
Taxes: 10%
$2,186 - $8,474 /night
Karma Bay
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%