Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$1,020 - $3,800 /night
Belair
6 Bedroom Villa, 5 Bathrooms, Sleeps 12
The Sugar Hill Resort community offers a number of resort amenities. Guests will have access to the Clubhouse, restaurant, resort swimming pools and tennis courts.
Please note: The beach experiences s... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12.5%
Taxes: 12.5%
$1,007 - $3,457 /night
Pastels
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The vacation rental villa Pastels is a beautiful property located in Vitet in the heart of a peaceful and green environment, in front of the sparkling ocean. Spacious and bright, this four-bedroom house with a swimming p... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $4,286 /night
Indigo
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The vacation rental Indigo is a beautiful three-bedroom property with a pool, ideally located in St-Jean, facing a breathtakingly beautiful view over the ocean and Lorient Bay. Modern and bright, this holiday home provid... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $4,300 /night
Villa Agama
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Discover the stunning Villa Agama and its breathtaking views.
Recently renovated and ideally located in the heart of the prestigious Terres Basses gated community, this villa perfectly blends elegance and comfort.
... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,000 - $4,286 /night
Tulum
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Villa Tulum is a charming Caribbean property located in Gustavia, nestled in a breathtaking setting. Close to the vibrant capital of St-Barths, this two-bedroom villa rental welcomes you with its swimming pool, its brigh... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $3,000 /night
Ocean Breeze Villas
4 Bedroom Villa, 6 Bathrooms, Sleeps 8
Experience luxury living at its finest in these stunning Villas nestled in the exclusive Indigo Bay, Sint Maarten.
Step outside to your private oasis at Ocean Breeze Villa B featuring a heated pool, BBQ area, and sun-... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,000 - $2,860 /night
Tortuga B19
5 Bedroom Villa, 5 Bathrooms, Sleeps 12
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,000 - $7,857 /night
Takamaka
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
The vacation rental villa rental Takamaka is a superb two-bedroom property ideally located in Grand-Cul-de-Sac, overlooking the breathtaking ocean view. Facing the sparkling ocean in a privileged environment, this vacati... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $3,857 /night
Flamand Escape
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Nearby construction may result in noise disturbances. For further details on how this might affect your stay, please reach out to a Rental Escapes villa specialist.
The holiday rental villa Flamands E... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $4,571 /night
Ocean Palm
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Ocean Palm is nestled on the heights of Gouverneur. The view is breathtaking.
Newly built, the villa has a modern kitchen and a comfortable bright living room. The terrace offers a dining area as well as an outdoor lo... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 /night
Little Waters Villa
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Little Waters on the Cliff is an exclusive private villa nestled on the cliffside at the westernmost point in Jamaica allowing guests to have an uninterrupted view of the setting sun. The house is architecturally designe... more
Additional Fees: Damage Waiver $299.00 flat
$1,000 - $3,143 /night
Villa Hill
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Villa Hill is a charming three-bedroom property located in St-Jean in front of a fantastic view over the bay and the ocean. Nestled in the heart of the green rolling hills, Villa Hill is a true haven of peace, a most rel... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $3,200 /night
Sunny Bay Estates | Villa Alexis
4 Bedroom Villa, 5 Bathrooms, Sleeps 10
Sunny Bay Estates is located on a peninsula overlooking the warm waters of Silly Creek. This gated community offers four spectacularly appointed luxury vacation villas, white sandy beaches, private pools, kayaks, paddle ... more
Additional Fees: Cleaning Fee $1000.00 flat, Damage Waiver $299.00 flat
Taxes: 12%
Taxes: 12%
$1,000 - $1,500 /night
Villa Deluxe Paradise
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Located in the cool hills of Discovery Bay, Jamaica, Villa Deluxe Paradise Vacation Home is a tranquil retreat blessed with world-class views across the Caribbean Sea. Once designed as a dream home, this exceptional vill... more
Additional Fees: Damage Waiver $299.00 flat
$1,000 - $1,714 /night
Blue Opal
5 Bedroom Villa, 4 Bathrooms, Sleeps 10
Blue Opal is a gem in the heart of Pelican Key in St. Maarten. As you open the front door, you are greeted with a marvelous view of the ocean. The distinctive aqua-colored kitchen is well laid out and a favorite with pri... more
Additional Fees: Cleaning Fee $250.00 flat, Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,000 - $3,429 /night
Le Rocher
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
The stunning Villa Le Rocher is a five-bedroom jewel, it sits in the hills of the Terres Basses area of St. Martin and offers visitors stunning views of Simpson Bay as well as uninterrupted views of both the Atlantic and... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,000 - $7,143 /night
Terre Indigo
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Nestled on the heights of St. Jean, rental villa Terre Indigo overlooks Nikki Beach, Eden Rock and Pelican Beach. With its fantastic view over the ocean and the neighbouring islets, this four-bedroom vacation home is the... more
Taxes: 15%
$1,000 - $1,575 /night
Rosso di Sera
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Rosso di Sera is your own special hideaway in the Turks & Caicos Islands. As you ascend the native stone stairs, you'll know you have reached your own secluded sanctuary.
Your island home awaits you, complete with you... more
Additional Fees: Cleaning Fee $300.00 flat, Damage Waiver $299.00 flat
Taxes: 22%
Taxes: 22%
$1,000 - $4,143 /night
Nolen
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Nestled in the hills of Grand-Cul-de-Sac, rental villa Nolen offers a splendid view over the lagoon and the ocean. The environment is truly enchanting in the breeze blowing gently through the arched doors characteristic ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $4,285 /night
Amethyst
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
From its privileged cliffside position overlooking the Pointe du Bluff in Terres Basses, on French St. Martin’s northern coastline, Villa Amethyst is nestled between the Baie aux Cayes and the spectacular natural rock ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,000 - $5,714 /night
Feyrouz
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Ideally located on the heights of Vitet in St-Barths, the luxurious rental villa Feyrouz opens onto an amazing view over the ocean, the hills and the lagoon of Grand-Cul-de-Sac. This modern five-bedroom house is the perf... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $3,571 /night
Villa Golden View
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
The vacation rental Golden View is a luxurious property located in Vitet in front of a breathtakingly beautiful panorama. Nestled on the hillside, it overlooks Lorient bay and the neighbouring islands lightened in the ev... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $3,500 /night
Lo Scoglio
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The beautiful rental villa Lo Scoglio is a true haven of peace, located in the quiet and secluded residential area of Anse des Lézards. With a breathtaking view over the wild bay, the property is very private, and is th... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $5,286 /night
Lenalee
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Located on the heights of Flamands, villa Lenalee is a sumptuous four-bedroom property with a splendid panoramic view over the ocean and the hills. This luxurious house is the perfect place for a family or a group of fri... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $3,429 /night
Good Vibrations
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Located on the heights of St.Jean and close to all amenities, the charming rental villa Good Vibrations in St-Barths offers an amazing ocean view and a long-heated infinity pool. As it consists of two bedrooms, this rent... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $2,645 /night
On the Rocks Estate
7 Bedroom Villa, 4 Bathrooms, Sleeps 14
Welcome to On The Rocks. This oceanfront gated estate is conveniently located 20 minutes from the airport in the planned residential community of Beach Bay.
The dozen or so homes along this rugged coastline share a k... more
Additional Fees: Departure Cleaning Fee $195.00 flat, Damage Waiver $299.00 flat, Cleaning | Damage Deposit $2500.00 flat
Taxes: 28%
Taxes: 28%
$1,000 - $2,688 /night
Luxury Pool 1 BDM Suite
1 Bedroom Villa, 1 Bathrooms, Sleeps 2
The Luxury Pool One-Bedroom Suites are preferred by couples traveling with a child - they accommodate three comfortably. Explore our property in an electric golf cart and head for the Eden Roc Beach Club for some rest an... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 28%
Taxes: 28%
$1,000 - $3,143 /night
Passage
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Located above Corossol Beach, villa Le Passage is a luxurious contemporary property with stunning ocean views. Spacious and bright, this vacation home with a heated swimming pool welcomes guests in the utmost calm and na... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $2,290 /night
Hacienda A18 | Tranquila
4 Bedroom Villa, 5 Bathrooms, Sleeps 10
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,000 - $4,000 /night
Shell Beach
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Located in Gustavia, a few steps from the splendid “shell beach”, the vacation villa Shell Beach is a charming two-bedroom property nestled in the green hills. The daily spectacle of the glowing sunsets and the view ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $7,143 /night
Ocean Five
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Located on the heights of Flamands, the rental Villa Ocean's 5 is a stunning property that opens onto a magnificent view over the ocean and the surrounding hills. In a lush tropical setting near the beautiful Flamands be... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $3,000 /night
La Cana H3 | Caballet
4 Bedroom Villa, 5 Bathrooms, Sleeps 10
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,000 - $4,286 /night
Casaroc
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Casa Roc is a very nice three-bedroom villa ideally located in the centre of Gustavia, within walking distance of the restaurants, shops and Shell Beach.
The view on Gustavia harbour is amazing. At night, the city and... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $2,857 /night
Fairwinds
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,000 - $3,200 /night
Sea Grapes
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Sea Grapes is a charming and well-appointed three-bedroom beach villa with separate 3three-bedroom cottage. The villa is located on a private white sand beach on exclusive Fortlands Road in Discovery Bay.
The two-sto... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 5%
Taxes: 5%
$1,000 - $2,450 /night
Portico 1
3 Bedroom Condo, 4 Bathrooms, Sleeps 6
Portico 1 is an impressive oceanfront property offering three bedrooms, three and a half bathrooms within 3,500 square feet of living space featuring cutting-edge finishes, luxurious furnishings and outstanding amenities... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12.5%
Taxes: 12.5%
$1,000 - $2,500 /night
Zen
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Ideally located in Pointe-Milou in front of the ocean, villa Zen is a charming two-bedroom property with a beautiful tropical garden. Spacious and bright, this Caribbean-inspired house with a swimming pool and heated jac... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $1,571 /night
Blue Heaven Villa
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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, Service Fee $50.00 flat
$1,000 - $3,143 /night
Armor
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Nestled in the heights of the exclusive private domain of Montjean, Villa Armor welcomes you into an exceptional setting where nature, privacy, and comfort meet.
Surrounded by a lush tropical garden, this charming vil... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $3,857 /night
Agave Azul
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Located on the high hills of Vitet, the luxurious rental Agave Azul is the perfect place for a great vacation in a charming environment. Built on two levels, it opens widely onto a fantastic panoramic view over the bay o... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,000 - $3,429 /night
Ecume des Jours
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Villa L'Ecume des Jours boasts an ideal location on the stunning Plum Bay beach, where it merges with Baie Longue. This contemporary beachfront property offers a tranquil setting for your vacation.
The villa features ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,000 - $2,000 /night
Beach Shack
1 Bedroom Villa, 1 Bathrooms, Sleeps 2
A beguiling bolthole for couples that blends Balinese style and boho vibes. Offering all the ingredients for an intimate getaway, and an ideal location at the end of Turtle Cove beach, where passing beachgoers are few an... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12%
Taxes: 12%
$999 - $2,299 /night
Tortuga C32
4 Bedroom Apartment, 4 Bathrooms, Sleeps 8
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$999 - $1,675 /night
Affiniti
4 Bedroom Villa, 3 Bathrooms, Sleeps 8
20 minutes away from Providenciales International Airport, this spacious home sits perched overlooking Chalk Sound Creek and ocean. With a stunning sunset view, an amazing infinity pool, which is one of the highlights of... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12%
Taxes: 12%
$996 - $2,251 /night
Lockrum Point
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Sitting on Lockrum Bay, this amazing two-level seaside villa sets the stage for luxurious relaxation, privacy, and entertainment. The villa comes with breathtaking views of the sea and St. Martin, four ensuite bedrooms/b... more
Additional Fees: Damage Waiver $299.00 flat
$995 - $2,395 /night
Iggy Blue
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
This 5,000+ square foot villa is directly oceanfront in Rum Point just 2 miles east of the Rum Point Club (reopening Spring 2023). The name Iggy Blue pays homage to Grand Cayman's indigenous, and protected blue iguana.
... more
Additional Fees: Departure Cleaning Fee $295.00 flat, Cleaning | Damage Deposit $2500.00 flat, Damage Waiver $299.00 flat
Taxes: 30.9%
Taxes: 30.9%
$995 - $1,695 /night
3 BDM Beachview Villa
3 Bedroom Apartment, 3 Bathrooms, Sleeps 6
Spacious living and dining areas, fantastic ocean views, and a private plunge pool are just a few reasons why the Beachview Villas are irresistible vacation accommodations.
Located steps away from Dawn Beach, offers w... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 20%
Taxes: 20%
$995 - $2,495 /night
Coral Kai
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Welcome to Coral Kai, an oceanfront villa along the north shore in beautiful Rum Point. This spacious single-level home invites you to experience beachfront living in its purest form.
Unwind on the sandy beachfront th... more
Additional Fees: Departure Cleaning Fee $245.00 flat, Damage Waiver $299.00 flat, Cleaning | Damage Deposit $2500.00 flat
Taxes: 30.9%
Taxes: 30.9%
$994 - $2,763 /night
No Problem
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $2500.00 flat
Taxes: 17.5%
Taxes: 17.5%
$990 - $3,500 /night
Tortuga C35
5 Bedroom Villa, 6 Bathrooms, Sleeps 14
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%