Caribbean Vacation Rentals
Luxury Villa Rentals in Caribbean for 2+ people
$1,095 - $2,395 /night
Wind Upon the Waves
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Welcome to Wind Upon the Waves, a newly built, single-level home on the island's South Coast. The owners have designed this 5,000-square-foot gated residence for privacy and exceptional panoramic views of the south coast... more
Additional Fees: Departure Cleaning Fee $295.00 flat, Damage Waiver $299.00 flat, Cleaning | Damage Deposit $2500.00 flat
Taxes: 30.9%
Taxes: 30.9%
$1,095 - $2,845 /night
Kai-Yak Cove
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Kai-yak Cove is a newly-built luxury Caribbean-style villa in the tranquil resort neighbourhood of Cayman Kai. Guests will enjoy many unique features, including a wrap-around veranda, a pool with a heated spa, an outdoor... more
Additional Fees: Departure Cleaning Fee $395.00 flat, Damage Waiver $299.00 flat, Damage Deposit | Excess Cleaning $2500.00 flat
Taxes: 30.9%
Taxes: 30.9%
$1,095 - $2,845 /night
White Dahlia
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Welcome to White Dahlia. This multi-windowed, open-concept floor-plan offers up to 10 guests an opportunity to spend their vacation free of clutter with smart home technology and luxurious amenities.
Soaring ceilings,... more
Additional Fees: Departure Cleaning Fee $245.00 flat, Damage Waiver $299.00 flat, Damage Deposit | Excess Cleaning $2500.00 flat
Taxes: 30.9%
Taxes: 30.9%
$1,095 - $2,895 /night
Kai Vista
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Welcome to Kai Vista, a recently remodeled 4-bedroom, 4-bath villa perched on an elevated ridge in Rum Point with a private pool and heated spa.
Grab your nice shades and head down to the beachfront sundeck lined with... more
Additional Fees: Departure Cleaning Fee $395.00 flat, Damage Waiver $299.00 flat, Cleaning | Damage Deposit $2500.00 flat
Taxes: 30.9%
Taxes: 30.9%
$1,092 /night
Palma Verde Retreat
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%
$1,092 - $2,358 /night
Serenity by the Sea
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Serenity is one of the most beloved and often revisited villas on Jamaica's beautiful north coast. Its prize location is a waterfront acre 8 miles west of Montego Bay. Grounds include a shared tennis court, basketball ho... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,090 - $2,018 /night
Oceanfront Studio at Alexandra Resort
1 Bedroom Hotel, 1 Bathrooms, Sleeps 2
Oceanfront Studios overlooks Grace Bay Beach and affords ocean views from the balcony or terrace. Each Studio feature a king bed, bathroom with stand-up shower, air-conditioning and ceiling fan, flat screen television wi... more
Additional Fees: Damage Waiver $299.00 flat
$1,089 - $4,235 /night
Mahogany Drive 7
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Royal Westmoreland is one of the Caribbean's finest luxury golf communities. With the $10 per person per day fee, guests will have access to the gym ($), golf course ($), tennis courts ($), Club House ($), beach ... more
Additional Fees: Damage Waiver $299.00 flat, Security Monitoring $120.00 daily
Taxes: 12.5%
Taxes: 12.5%
$1,086 - $6,429 /night
Rose Dog
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Located on a hillside in Dévé, the vacation rental Rose Dog is a superb four-bedroom property with spectacular views over the Caribbean Sea from Petit-Cul-De-Sac to Toiny Bay. Very private and equipped with utmost comf... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,080 - $2,360 /night
Hacienda 82
4 Bedroom Villa, 5 Bathrooms, Sleeps 10
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,080 - $2,700 /night
Hacienda A13 | Buena Vida
4 Bedroom Villa, 5 Bathrooms, Sleeps 10
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,077 - $3,429 /night
Encore
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
You arrive at Encore along a long, inviting drive filled with palms, exotic tropical flowers, trees, and shrubs. Beautiful gardens fill the entry courtyard and completely surround the villa. The Moorish inspired soaring ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,074 - $2,330 /night
Coconut Palm Villa
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
Coconut Palm Villa is a luxurious three-bedroom oasis literally steps away from one of the world’s best beaches – Meads Bay. This exceptional villa is within easy walking distance of many of the West End’s gourmet ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 23%
Taxes: 23%
$1,072 - $2,985 /night
Etoile de Mer
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Etoile de Mer is located on the edge of the Caribbean Sea in a private residential development known as Shore Pointe. You get the best of both worlds when staying at Etoile de Mer. You are beachfront and walking distance... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,071 - $3,929 /night
Kailio
3 Bedroom Villa, 2 Bathrooms, Sleeps 6
Located on the heights of Colombier, the beautiful vacation Villa Kailio in St. Barths offers a breathtaking view over the ocean and the glowing sunsets. Close to Flamands Beach and restaurants, this three-bedroom vacati... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,071 - $5,000 /night
Roy
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Villa Roy in St. Barths is a magnificent four-bedroom property overlooking the lagoon and the ocean, in the heart of a green environment. Located in Vitet, it offers a high level of services, making it the ideal place fo... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,071 - $3,571 /night
Fun and Sun
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Fun and Sun is a brand new villa in St Jean. Good walkers will go to the beach, shops and restaurants on foot. The long heated pool overlooks the pond and St Jean Bay. Two of the bedrooms are accessible by the living, th... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,071 - $7,143 /night
La Bella Casa
12 Bedroom Villa, 12 Bathrooms, Sleeps 24
La Bella Casa is a charming Caribbean estate surrounded by lush tropical gardens and sprawling green lawns. The views overlooking the elegant La Samanna Hotel, Baie Longue Beach and the deep blue Caribbean dazzle morning... more
Additional Fees: Security Deposit $5000.00 flat
Taxes: 10%
Taxes: 10%
$1,071 - $3,571 /night
Sand Castle
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Villa Sand Castle is a beautiful holiday rental located on the white sandy beach of Lorient. Very bright and comfortable, this four-bedroom beach house is the perfect vacation spot for a group of friends wishing to enjoy... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,071 - $3,214 /night
Bel Roc
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Located in the Flamands area, the charming vacation rental Bel Roc opens onto a stunning view over the bay and the deep blue ocean. It is very close to the 5* Cheval Blanc-Isle de France Hotel and Flamands beach. This tw... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,071 - $3,571 /night
Flamands Bay
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.
Located only a few steps away from ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,071 - $6,429 /night
Santa Alicia
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
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.
Located on the heights of Flamands,... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,071 - $3,857 /night
Clementine
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Located on the heights of Vitet, the villa rental Clementine is a three-bedroom property with a swimming pool and breathtaking ocean views. Spacious and comfortable, this vacation home in St-Barths offers luxurious, brig... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,071 - $3,960 /night
Sunrise
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,071 - $3,214 /night
Luz
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Vacation villa Luz is a charming four-bedroom property facing the ocean. Located in Lorient, it offers splendid views over the sunsets, in the heart of Saint Barths hills. This charming four-bedroom villa is the perfect ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,070 - $2,500 /night
Azure Wish Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
A short drive from Spanish Town along the stunning Nail Bay road takes visitors to the beautiful and exclusive villas of the Nail Bay Resort. Guests arriving at Azure Wish are welcomed to an expansive driveway, surround... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 22%
Taxes: 22%
$1,069 - $1,749 /night
Bahia Mar Villa
2 Bedroom Villa, 3 Bathrooms, Sleeps 4
Featuring garden, ocean and oceanfront views, our stylish two-bedroom, two-and-a-half-bath Bahia Mar luxury villas average 2,315 square feet, spread out over two levels. The first floor features the bedrooms and en-suite... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 30%
Taxes: 30%
$1,066 - $4,929 /night
Minou
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Located in Grand-Cul-de-Sac near the beaches and shops, the charming rental villa Minou opens onto a splendid view over the ocean, the bay and the hills. In an enchanting environment, this four-bedroom vacation home is p... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,060 - $1,645 /night
Ocean View Suite | Ridgetop
1 Bedroom Hotel, 1 Bathrooms, Sleeps 2
Featuring Ocean views, a private wrap-around terrace, kitchenette and bathroom with an oversized shower, soaking tub and an option of one king bed or two double beds (on request based on availability). This suite is cite... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 31.25%
Taxes: 31.25%
$1,057 - $4,393 /night
The One
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Located near Flamands and Saint-Jean, the luxurious villa The One is a splendid property in front of the ocean and the Bonhomme and Frégate islands. In a paradise setting of green hills, this three-bedroom vacation home... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,057 - $6,000 /night
Vague Bleue
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
The vacation rental Vague Bleue is a sumptuous property located on the heights of Lurin, only a few minutes from the beach and shops. With a spectacular view over the glowing sunsets on the ocean, this three-bedroom home... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,056 - $1,763 /night
Blue Lagoon
3 Bedroom Villa, 3 Bathrooms, Sleeps 10
Offering the best of indoor/outdoor living, Blue Lagoon’s Great Room is exquisitely furnished by Janus et Cie and Dedon and includes a gourmet kitchen, wet bar, formal dining room, and entertainment area. The master be... more
Additional Fees: Security Deposit $299.00 flat
Taxes: 22%
Taxes: 22%
$1,054 - $3,126 /night
2 BDM Deluxe Oceanfront Suite at Windsong Resort
2 Bedroom Condo, 2 Bathrooms, Sleeps 4
This generous, airy suite with 1968 square feet, ten-foot ceilings and Travertine marble floors feels more like a home than a vacation suite. Upon entry, delightfully open interiors boast a magnificent backdrop of turquo... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 27%
Taxes: 27%
$1,050 - $3,000 /night
Jaguey 3
4 Bedroom Villa, 6 Bathrooms, Sleeps 8
Jaguey 3, a stunning 4-bedroom villa, epitomizes the essence of Caribbean elegance. Nestled in the heart of the Arrecife community within the prestigious Puntacana Resort & Club, this property offers breathtaking views o... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,050 - $3,949 /night
Noble House
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
This accommodation includes complimentary access to the Ocean Cliff Hotel in Negril, an 80-minute drive from the villa. You can enjoy their ocean-fed pool and sandy beach. Additional services such as meals from ... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,050 - $2,000 /night
Calabash Deluxe Suite
1 Bedroom Apartment, 1 Bathrooms, Sleeps 2
Calabash Luxury Boutique Hotel & Spa combines five-star service and luxury within a relaxed and intimate environment to create the ultimate Caribbean escape.
Bright and airy suites that boast large lounge areas separa... more
Additional Fees: Damage Waiver $299.00 flat
$1,050 - $4,150 /night
Roc E Mar
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Villa Roc E Mar is a sumptuous property located in Toiny on Saint-Barths’ wild coast. The landscapes that surround this modern-architecture vacation rental make a unique atmosphere for a most luxurious stay listening t... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,050 - $2,800 /night
High Spirits
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Royal Westmoreland is one of the Caribbean's finest luxury golf communities. With the Social Membership included in this villa, guests will have access to the gym ($), golf course ($), tennis courts ($), Club Hou... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 12.5%
Taxes: 12.5%
$1,050 - $2,985 /night
Beaulieu
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Perched above the shimmering turquoise waters of the Caribbean Sea, Villa Beaulieu offers an extraordinary vantage point over Baie Rouge Beach, with uninterrupted views stretching toward the neighboring island of Anguill... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,045 - $1,900 /night
Oceanfront Grand Studio
1 Bedroom Hotel, 1 Bathrooms, Sleeps 2
Located in an oceanfront building complete with a sprawling beach view, this 670 square foot room features one king bed, a fully-outfitted luxury bathroom with shower and separate spa tub, kitchenette (no stove) and indo... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 28%
Taxes: 28%
$1,045 - $1,750 /night
Cayman Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Cayman Villa is a bright, breezy four-bedroom villa with spectacular views at Cap Estate, the northernmost point of Saint Lucia. The first thing you will note about Cayman Villa is the light. Travertine tile and coral wa... more
Additional Fees: Damage Waiver $299.00 flat
$1,040 - $1,850 /night
La Sérénité
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
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%
$1,039 /night
Villa Blue
5 Bedroom Apartment, 6 Bathrooms, Sleeps 10
Guests staying within Puntacana Resort & Club will have access to all resort amenities and facilities. Resort amenities and facilities include two golf courses ($), two beach clubs ($), Six Senses Spa ($), restau... more
Additional Fees: Security Deposit $299.00 flat
Taxes: 18%
Taxes: 18%
$1,039 /night
Tropical Zen Escape
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Set along the picturesque Caribbean Sea is La Cana Beach Club. Guests have access to all Club facilities including the swimming pool, lounge chairs, showers, tables and chairs, restaurant ($) and bar ($).... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 18%
Taxes: 18%
$1,029 - $5,429 /night
Ocean's 21
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Ocean’s 21 is a magnificent 4-bedroom villa located in the quiet district of Petit Cul de Sac. With beautiful sea views, it offers an idyllic setting for a peaceful, relaxing stay with family or friends.
The villa�... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,029 - $4,143 /night
Amalie
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Located on the heights of Marigot, the vacation rental Amalie is a property built over three levels in front of a magnificent view of the ocean and the rolling hills of St-Barths. Spacious and luxurious, this vacation ho... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,029 - $3,000 /night
Caramba
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
The villa rental Caramba is a charming Caribbean property located in Pointe-Milou, facing a breathtakingly beautiful view. Its vast spaces are bright and comfortable, with its many openings overlooking the ocean and the ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,029 - $3,714 /night
Enzuma
3 Bedroom Villa, 2 Bathrooms, Sleeps 6
The charming holiday rental villa Enzuma is located in the heights of Toiny and opens onto an amazing view over the beautiful ocean. The wild coastline is one of the quietest areas in St-Barths and a playground for runne... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,029 - $2,886 /night
Villa Paradiso
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
Situated in the lush green hills of Sint Maarten in the exclusive area of Oyster Pond Estates is Paradiso, a six-bedroom, six-and-a-half bath villa. It is truly a gem of a villa. The minute you walk through the magnifice... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 9%
Taxes: 9%
$1,022 - $2,985 /night
Farniente
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Villa Farniente in Sint Maarten is a gorgeous and exceptionally popular villa rental located at the beautiful Shore Pointe on the exclusive, scenic Cupecoy Beach. This fully air-conditioned property offers a prime holida... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%