Caribbean Vacation Rentals

Luxury Villa Rentals in Caribbean for 2+ people

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$1,700 - $5,000 /night

The Royal Westmoreland House

6 Bedroom Apartment, 6 Bathrooms, Sleeps 12
Located in the exclusive Royal Westmoreland Resort, The Royal Westmoreland House is a beautiful three-story villa with picturesque views of the Caribbean Sea. Nestled within the prestigious Royal Westmoreland Resort, ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12.5%
$1,700 - $3,600 /night

Palm Tree Villa

4 Bedroom Apartment, 3 Bathrooms, Sleeps 8
Guests staying within the world famous Sandy Lane Estate will have complimentary access to all Clubhouse facilities including beach chairs, umbrellas and tennis courts. Nestled within the prestigious ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12.5%
$1,700 - $5,750 /night

Angel Point

5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Villa Angel Point is a luxurious five-bedroom retreat on Anguilla's tranquil Caribbean coast. Completely renovated in 2023, this contemporary villa in Anguilla offers breathtaking views of St. Martin from its sun-soaked ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 23%
$1,700 - $3,000 /night

Cerezas Modern

5 Bedroom Apartment, 5 Bathrooms, Sleeps 10
All guests must register with the Casa de Campo Concierge office, and for a small daily fee ($30 per adult per night & $15 per child per night), are granted access to resort areas and amenities. Casa de Campo Res... more
Additional Fees: Damage Waiver $299.00 flat, Food & Beverage Deposit $500.00 flat
Taxes: 18%
$1,700 - $7,500 /night

Big Chill

6 Bedroom Villa, 7 Bathrooms, Sleeps 12
Big Chill is an expansive, modern home nestled in the prestigious canal system of Leeward, Providenciales, offering direct access to the islands’ waterways and effortless exploration by watercraft. With open living spa... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12%
$1,700 - $6,600 /night

Alinna

5 Bedroom Villa, 7 Bathrooms, Sleeps 10
Alinna is a contemporary oceanfront villa nestled along the serene shoreline of Chalk Sound National Park in Providenciales, Turks and Caicos Islands. Set against the lagoon’s luminous teal waters and dramatic limeston... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 22%
$1,700 - $5,300 /night

Monkey Hill

8 Bedroom Villa, 9 Bathrooms, Sleeps 16
Surrounded by tropical greenery within the sought-after Sugar Hill community in St. Peter, Monkey Hill offers a spacious six-bedroom luxury villa for families and groups seeking a relaxed Caribbean vacation. With generou... more
Additional Fees: Damage Waiver $299.00 flat, Security Deposit $2500.00 flat
Taxes: 12.5%
$1,700 - $4,280 /night

1 BDM Oceanfront Suite at The Palms Turks & Caicos

1 Bedroom Condo, 1 Bathrooms, Sleeps 2
The meticulously-designed, spacious 1,500 square foot one bedroom suites at The Palms Turks & Caicos offer a comfortable king bed with custom-made, premium bed linens. Features include one and a half luxury bathrooms wit... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 27%
$1,700 - $6,500 /night

Cocomaya at Apes Hill Club

5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Refresh your body and soul at Apes Hill Golf & Beach Club. Guests will have complimentary access to all Club facilities including the Beach Club, swimming pool, Pool Club, tennis courts, restaurants and bars.... more
Additional Fees: Damage Waiver $299.00 flat, Security Deposit $2500.00 flat
Taxes: 12.5%
$1,700 - $4,950 /night

Kaiku

6 Bedroom Villa, 5 Bathrooms, Sleeps 12
Welcome to Kaiku, a lavishly landscaped, beachfront gated estate in Cayman Kai. This sprawling villa sits on a double lot consisting of a six-bedroom, two-story main house plus an optional detached two-bedroom guest ... more
Additional Fees: Departure Cleaning Fee $495.00 flat, Damage Waiver $299.00 flat
Taxes: 30.9%
$1,700 - $5,000 /night

Casa Barana

6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Casa Barana is a superb, modern Tuscan-style beachfront six-bedroom villa located in the private gated community of Thompsons Cove, directly on 135 feet of tranquil, oceanfront paradise. The west wing consists of five la... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12%
$1,700 - $5,821 /night

Windrush

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%
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