Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$1,571 - $9,571 /night
Nala
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
This rental villa in St. Barths Nala is a beautiful property nestled on a hill above Grand-Cul-de-Sac. This five-bedroom vacation rental is located only a few steps from the beach and water activities, a perfect place fo... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,571 - $7,429 /night
Summertime
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The villa rental Summertime is a magnificent property ideally located in Pointe-Milou facing a breathtakingly beautiful ocean view. Consisting of four comfy bedrooms and a sparkling swimming pool, Villa Summertime offers... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,571 - $5,714 /night
Nikki
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Overlooking the blue and placid bay of St Jean, Villa Nikki offers contemporary style with beautiful panoramic views. The terrace is embraced by natural foliage and swaying palms, with a mirror-like infinity pool reflect... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,571 - $5,429 /night
Mamiami
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Nestled on a hillside in the quiet Vitet neighbourhood, the luxury rental villa Mamiami in St-Barths is a beautiful new property, which perfectly combines the charm of a classic island-inspired architecture with a refine... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,571 - $7,143 /night
Star
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The luxury rental villa Star is located on the heights of Camaruche, facing the breathtaking view over the Lorient bay and the neighbouring islands. Close to all amenities, this two-level villa is one of the most appreci... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,571 - $5,600 /night
Windrush
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
Taxes: 17.5%
$1,571 - $10,000 /night
Serenity
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Villa Serenity is a charming property located in the heights of Gustavia in front of a fantastic panorama. Recently renovated, this vacation home with a swimming pool consists of three bedrooms, and will offer a fourth b... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,560 - $2,800 /night
Cerezas Modern
5 Bedroom Apartment, 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%
$1,560 - $3,910 /night
Bananaquit
5 Bedroom Villa, 7 Bathrooms, Sleeps 10
Bananaquit is a luxurious villa for holiday rental located on the Sugar Hill Resort. This property is strategically located at the end of Plantation Drive in Barbados which offers the guests much privacy. Offering 3 bedr... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12.5%
Taxes: 12.5%
$1,550 - $3,795 /night
Our Cayman Cottage
7 Bedroom Villa, 8 Bathrooms, Sleeps 20
Welcome to Our Cayman Cottage! A private retreat, hidden in the East End along the reef-protected coast, this stunning home features elevated ocean views and luxurious resort-like amenities.
Spanning 6,500-square feet... more
Additional Fees: Departure Cleaning Fee $195.00 flat, Damage Waiver $299.00 flat, Cleaning | Damage Deposit $2500.00 flat
Taxes: 30.9%
Taxes: 30.9%
$1,550 - $5,000 /night
Old Trees 102 | Firefly
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Firefly at Old Trees is a five-bedroom beachfront holiday villa in Barbados. This luxury home sits privately in the Old Trees development on the Platinum Coast of the island. This lateral apartment covers an entire floor... more
Additional Fees: Security Deposit $2500.00 flat
Taxes: 12.5%
Taxes: 12.5%
$1,550 - $2,850 /night
Villa Turquesa
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
On the shores of Sapodilla Bay, Villa Turquesa offers a unique blend of luxurious amenities and laid-back island style. Located within the Ocean Point Drive Community, this expansive 4,750 sq.-ft. home features exquisite... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12%
Taxes: 12%
$1,550 - $4,750 /night
Old Trees 302 | La Mirage
4 Bedroom Apartment, 5 Bathrooms, Sleeps 8
La Mirage is a luxury beachfront penthouse holiday apartment on the West Coast of Barbados. Up to eight guests can comfortably stay in this villa’s four en-suite bedrooms and children are also welcome. This Barbados ho... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12.5%
Taxes: 12.5%
$1,543 - $3,571 /night
Jamaican Me Happy
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$1,525 - $3,750 /night
Happy Trees
4 Bedroom Villa, 4 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.
Happy Trees is a magnificent fo... more
Additional Fees: Security Deposit $3000.00 flat
Taxes: 12.5%
Taxes: 12.5%
$1,500 - $3,000 /night
Pebble
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
Located on the secluded East Coast of Barbados, Pebble is a beachfront, holiday villa that blends with the earth itself, bearing all the perfect imperfections of the rugged, windswept side of Barbados. Designed by Sophie... more
Additional Fees: Security Deposit $2500.00 flat
Taxes: 12.5%
Taxes: 12.5%
$1,500 - $5,850 /night
Love and Livity
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,500 - $4,714 /night
Beau Rivage
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
Beau Rivage, an exclusive retreat nestled along the pristine shores of Baie Rouge Beach in St Martin. Baie Rouge Beach, nearly a mile of soft sand, is a tranquil and naturally beautiful gem. This idyllic property is enve... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,500 - $3,143 /night
Abacus Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Guests of Abacus Villa 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 mand... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,500 - $5,500 /night
Tortuga H6 | Rosana
5 Bedroom Apartment, 7 Bathrooms, Sleeps 12
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,500 - $4,200 /night
Twin Palms Villas
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Twin Palms Villas is undoubtedly one of Anguilla’s most conveniently situated vacation homes. For larger parties, a two-bedroom Beach Palm Villa can be combined with a three-bedroom Coconut Palm Villa to create a spaci... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 23%
Taxes: 23%
$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 C... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,500 - $3,500 /night
Arrecife 48
5 Bedroom Villa, 6 Bathrooms, Sleeps 12
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,500 - $6,050 /night
Sandy Shore
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Sandy Shore is a 4-bedroom all-suite beachfront villa located on the Southside of Providenciales in the Turtle Tail region.
The villa boasts an open-concept kitchen and living room area, perfect for entertaining while... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 22%
Taxes: 22%
$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 e... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,500 - $4,000 /night
Sugar Apple Villa
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Only five minutes from award-winning Grace Bay Beach, Sugar Apple is a brand-new villa located on the serene, canal-side cul-de-sac of Kira Island.
Sitting directly on the Leeward Marina, opposite Mangrove Cay and wit... more
Taxes: 22%
$1,500 - $4,000 /night
Grand Outlook Villa
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Nestled within a gated compound, Grand Outlook offers an unparalleled sanctuary for tranquility and rejuvenation beneath the azure skies of Anguilla, situated at the island's second-highest point. This luxurious retreat ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 23%
Taxes: 23%
$1,500 - $10,000 /night
Hura Sea Villas
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
Perfectly placed on Long Bay Beach, Hura Sea Villas deliver pared-back, contemporary living in a classic island setting. Cooling sea breezes, azure waters, and gently lapping waves are only a step away from the main hous... more
Taxes: 22%
$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 t... more
Additional Fees: Damage Waiver $299.00 flat
$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 out... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12%
Taxes: 12%