Villa Rentals Caribbean and Anguilla Villas

East Side, Anguilla, British West Indies, 2 Bedrooms

This new Anguilla villa provides serene views of the gorgeous, clear blue Caribbean Sea.

Villa Rentals Caribbean and Anguilla Villas

Seafeathers Bay, Anguilla, 5 Bedrooms

Alcyon Villa is a beautiful 8,000 square foot Mediterranean style villa located seaside on the island of Anguilla.

Villa Rentals Caribbean and Anguilla Villas

Little Harbor, Anguilla, British West Indies, 1 Bedroom

Inspired by examples of contemporary Mexican architecture, this one bedroom villa has been designed with an eye to breathtaking vistas and comfortable, casual living, both indoors and out.

Villa Rentals Caribbean and Anguilla Villas

Sandy Hill Bay, Anguilla, British West Indies, 4 Bedrooms

This award-winning villa, located on Sandy Hill Bay beach, offers a unique blend of exquisite detail, spacious comfort, luxury, and quiet ambiance.

Villa Rentals Caribbean and Anguilla Villas

Blowing Point, Anguilla, British West Indies, 7 Bedrooms

Built of white stucco, the villa offers striking architecture and combines natural beauty with quiet elegance, while offering unrivaled views across the Caribbean Sea.

Villa Rentals Caribbean and Anguilla Villas

Little Harbor, Anguilla, British West Indies, 4 - 7 Bedrooms

Sitting on Anguilla's South Shore, Kamique commands its own secluded cove beach and stunning views towards the mountains of St. Martin.

Villa Rentals Caribbean and Anguilla Villas

North Hill, Anguilla, British West Indies, 4 Bedrooms

This charming, private villa offers an elegant and relaxed setting just for two, or a group of friends and family.

Villa Rentals Caribbean and Anguilla Villas

Anguilla, British West Indies, 3 - 7 Bedrooms

Zenaida Beach & Tennis Estate is nestled on three acres of lush tropical gardens with majestic, sweeping views of the Caribbean Sea, and the mountains of St. Martin and St Barts beyond.

Villa Rentals Caribbean and Anguilla Villas

Pelican Bay, Anguilla, British West Indies, 4 Bedrooms

Lockrum is an amazing new oceanfront villa on the southern coast of Anguilla. 

Villa Rentals Caribbean and Anguilla Villas

Limestone Bay, Anguilla, British West Indies, 4 Bedrooms

This 10,000 square foot villa has magnificent views of the Atlantic ocean. 

Villa Rentals Caribbean and Anguilla Villas

Dropsey Bay, Anguilla, British West Indies, 3 Bedrooms

Enjoy this beautiful 5,000 sq. ft. villa on a secluded beach, overlooking the Caribbean Sea.

Villa Rentals Caribbean and Anguilla Villas

Little Harbour, Anguilla, British West Indies, 9 Bedrooms

Set within a private tropical garden of approximately 1.5 acres, Indigo is the perfect holiday hideaway.

Villa Rentals Caribbean and Anguilla Villas

Little Harbour Bay, Anguilla, British West Indies, 10 Bedrooms

Le Bleu is placed on a beautifully landscaped ten acre site in fashionable Little Harbour Bay on the south shore of the island.

Villa Rentals Caribbean and Anguilla Villas

Lockrum, Anguilla, British West Indies, 6 Bedrooms

Enjoy immaculate views of the sea from this luxury villa.

Villa Rentals Caribbean and Anguilla Villas

East Shoal Bay, Anguilla, 4 Bedrooms

Summer Breeze, of our Caribbean Villas, is an ocean front home situated in a secluded area of East Shoal Bay in Anguilla.

Villa Rentals Caribbean and Anguilla Villas

Jopsey Bay, Anguilla, 4 Bedrooms

Located on Jopsey Bay, overlooking secluded Lover’s Cove along a dramatic Anguillian shoreline, Rum Punch Villa is a 7,500 square foot tropical retreat.

Villa Rentals Caribbean and Anguilla Villas

Little Harbour, Anguilla, 1 Bedroom

Perfect for the solo traveler or a couple, Little Butterfly provides a contemporary and affordable getaway vacation in the heart of Anguilla.

Caribbean Villas and Antigua Villas

Turtle Bay, Antigua, West Indies, 7 Bedrooms

Dolce Vita is a new multimillion dollar luxury Antigua villa rental, located directly on the cliff at Turtle Bay.

Caribbean Villas and Antigua Villas

Falmouth Harbour, Antigua, West Indies, 2 to 6 Bedrooms

Villa Sariel is in a superb Antigua villa rental location with breathtaking views over Falmouth Harbour.

Caribbean Villas and Antigua Villas

Dumm's Point, Antigua, West Indies, 4 Bedrooms

Villa Kulala sits close to a 40 foot cliff and has spectacular views across Dian Bay.

Caribbean Villas and Antigua Villas

Galley Bay, Antigua, West Indies, 5 Bedrooms

Enjoy the panoramic ocean views that this luxury villa has to offer.

Caribbean Villas and Antigua Villas

Jolly Harbour, Antigua, West Indies, 4 Bedrooms

Located on the pristine white sand beach of Jolly Harbour, Antigua, you will literally be steps away from the warm and tranquil Caribbean Sea.

Caribbean Villas and Antigua Villas

Jumby Bay, Antigua, West Indies, 3, 4, and 5 Bedrooms

Set on a 300 acre private island, Jumby Bay casts a spell of serene enchantment.

Caribbean Vacation Homes and Barbados Villas

Sandy Lane, Barbados, 9 bedrooms

Bon Vivant is a world class Barbados vacation villa rental located in Sandy Lane Estates.

Caribbean Vacation Homes and Barbados Villas

Sandy Lane, Barbados, 3 bedrooms

Situated in an acre of luxurious vegetation, Anchorage has a unique inside/outside feel to it.

Caribbean Vacation Homes and Barbados Villas

St. James, Barbados, 5 bedrooms

Weston House is a magnificent beach house on the west coast of the island with incredible views of the Caribbean Sea.

Caribbean Vacation Homes and Barbados Villas

St. James, Barbados, 6 bedrooms

Moon Dance is a stunning, private villa set in almost two acres of beautifully landscaped gardens on the renowned Sandy Lane Estate. 

Caribbean Vacation Homes and Barbados Villas

St. James, Barbados, 5 bedrooms

St. Helena has a beautiful beachfront location on the calm, clear waters of the west coast, and is also nearby to the historic Holetown.

Caribbean Vacation Homes and Barbados Villas

St. James, Barbados, 7 bedrooms

Jamoon is a fabulous villa featuring a mix of classical and contemporary styles. 

Caribbean Vacation Homes and Barbados Villas

St. James, Barbados, 3 bedroom house plus 2 bedroom cottage

Villa Melissa is a delightful, but very private villa set in tropical Caribbean gardens with its own path to the beach. 

Caribbean Vacation Homes and Barbados Villas

St. James, Barbados, 4 bedrooms

This is an incredible, luxury beachfront appartment, ideally perched on a bluff above a secluded beach. 

Caribbean Vacation Homes and Barbados Villas

St. James, Barbados, 7 bedrooms

Bruadair is a recently built villa situated in tropical surroundings and conveniently located near local shops, bars, and restaurants. 

Caribbean Vacation Homes and Barbados Villas

St. James, Barbados, 4 bedrooms

This is an exclusive new villa on the Sandy Lane Estate, and seldom can a more ideal setting for a luxury villa holiday be found. 

Caribbean Vacation Homes and Barbados Villas

St. James, Barbados, 3 bedrooms

Forest Hill 2 is a Deluxe Club Villa located on the exclusive Royal Westmoreland Golf Resort.  

Caribbean Vacation Homes and Barbados Villas

St. James, Barbados, 3 bedrooms

A delightful beachfront villa only a few feet away from the front deck patio to the Caribbean Sea below , Helena is a real beach lovers paradise.

Caribbean Vacation Homes and Barbados Villas

St. Peter, Barbados, 3 bedrooms

Waverly 1 is a private beachfront villa with a plunge pool and a secluded garden that leads directly onto Gibbs Beach. 

Caribbean Vacation Homes and Barbados Villas

St. James, Barbados, 6 bedrooms

Landfall House offers the ultimate in beachfront luxury, located right on famous Sandy Lane Beach, just north of Sandy Lane Hotel.  

Caribbean Vacation Homes and Barbados Villas

St. James, Barbados, 10 bedrooms

Cove Spring House is a luxurious 18,000 square foot vacation home, beautifully built on top of natural coral stone cliffs.

Cayman Island Villas and Rental Homes Cayman Island

Grand Cayman, Cayman Islands, 4 bedrooms plus 1 studio

Far Tortuga is the ideal beachfront Cayman Islands villa rental location for family vacations, couples traveling together, or romantic getaways.

Cayman Island Villas and Rental Homes Cayman Island

Grand Cayman, Cayman Islands, 4 bedrooms 

Sand Castle is a lovely, gated property located on the northside of the island in the quiet village of Old Man Bay.

Cayman Island Villas and Rental Homes Cayman Island

Grand Cayman, Cayman Islands, 4 bedrooms plus 2 bedroom guesthouse

This architecturally stunning villa is located in the east end of Grand Cayman Island, and often enjoys a trade wind breeze.

Caribbean Villas and Dominica Villas

Pointe Mulatre, Dominica West Indies, 1 Bedroom

Jungle Bay features 35 tastefully furnished tropical hardwood cottages, elevated on wooden posts, nestled beneath the undisturbed jungle of Dominica.

Caribbean Villas and Jamaica Villa Rentals

Discovery Bay, Jamaica, 5 bedrooms

Set on its own private white sand beach, Sea Grapes is a lovely waterfront Jamaica villa rental located on Discovery Bay.

Caribbean Villas and Jamaica Villa Rentals

Discovery Bay, Jamaica, 7 bedrooms

A favorite of celebrities and discerning vacationers, Amanoka promises a luxurious and relaxing Jamaica villa vacation.

Caribbean Villas and Jamaica Villa Rentals

Montego Bay, Jamaica, 4 bedrooms

Afimi Villa is a new oceanfront Jamaica villa rental in the Lagoons, an upscale gated community in Montego Bay.

Caribbean Villas and Jamaica Villa Rentals

Discovery Bay, Jamaica, 6 bedrooms

Keela Wee Villa is a magnificent two story, six bedroom, six bath Jamaica villa, situated on its own private white sand beach and swimming cove in Discovery Bay.

Caribbean Villas and Jamaica Villa Rentals

Discovery Bay, Jamaica, 7 bedrooms

Whispering Waters was completed in December 2006 and continues the tradition of Discovery Bay luxury villas.

Caribbean Villas and Jamaica Villa Rentals

Discovery Bay, Jamaica, 8 bedrooms

Mais Oui, a fully staffed Jamaica vacation rental, boasts a full suite of on-site amenities.

Caribbean Villas and Jamaica Villa Rentals

Montego Bay, Jamaica, 4 bedrooms 

Caribbean Villas and Jamaica Villa Rentals

Ocho Rios, Jamaica, 5 bedrooms

Scotch on the Rocks is the ideal Jamaica villa rental for family vacations, couples traveling together, or romantic getaways.

Caribbean Villas and Jamaica Villa Rentals

Montego Bay, Jamaica, 4 bedrooms

Beach House, one of the top Jamaica villas, is a prize location on a beachfront acre, located on a lovely calm body of water.

Caribbean Villas and Jamaica Villa Rentals

Discovery Bay, Jamaica, 8 bedrooms

At Coral Cove, two casual cottages share a delightful waterfront site on some of the clearest waters of all the Jamaica Villas.

Caribbean Villas and Jamaica Villa Rentals

Discovery Bay, Jamaica, 6 bedrooms

Makana is one of the most glamorous, private Jamaica villas on the precious strip of land that borders Discovery Bay.

Caribbean Villas and Jamaica Villa Rentals

Montego Bay, Jamaica, 5 bedrooms

Set on five acres of gently sloping land with a sea view, Great River House, one of the top Jamaica Villas, is the perfect, relaxing getaway.

Caribbean Villas and Jamaica Villa Rentals

Ocho Rios, Jamaica, 6 bedrooms

Directly on the beautiful, turquoise waters of Old Fort Bay, Malatai is one of the newest and largest Jamaica villas.

Caribbean Villas and Jamaica Villa Rentals

Discovery Bay, Jamaica, 5 bedrooms

On its own sugary white sand beach, lapped by the turquoise waters of Discovery Bay, sits the exquisite home Sugar Bay, one of the top Jamaica Villas.

Caribbean Villas and Jamaica Villa Rentals

Ocho Rios, Jamaica, 4 bedrooms

This is simply the most beautiful and luxurious villa in the Caribbean, “one of the best villas in the world.” (Condé Nast).

Caribbean Villas and Jamaica Villa Rentals

Montego Bay, Jamaica, 4 bedrooms

A paradigm of elegance and style, Noble House is an architectural gem, one of the most unique Jamaica Villas.

Caribbean Villas and Jamaica Villa Rentals

Discovery Bay, Jamaica, 7 bedrooms

Sundown, one of the most exquisite Jamaica Villas, is on a private white sand beach next to the beautiful turquoise waters of Discovery Bay.

Caribbean Villas and Jamaica Villa Rentals

Montego Bay, Jamaica, 6 bedrooms

Tranquillity, one of the top Jamaica Villas, is a place for relaxing into the calm ambiance of an exquisite beachfront home.

Caribbean Villas and Jamaica Villa Rentals

Runaway Bay, Jamaica, 6 bedrooms

Located on a wide sandy beach, Sweet Spot is like a pretty jewel box next to the sea.

Caribbean Villas and Jamaica Villa Rentals

Montego Bay, Jamaica, 4 bedrooms

Serenity is one of the most beloved and often revisited Jamaica villas on the beautiful north coast.

Caribbean Villas and Jamaica Villa Rentals

Discovery Bay, Jamaica, 7 bedrooms

At A Summer Place, one of the ideal Jamaica villas, enjoy mesmerizing panoramas of azure water and lush green hills.

Caribbean Villas and Jamaica Villa Rentals

Montego Bay, Jamaica, 4 bedrooms

Summerland Villa's unique location atop Round Hill offers magnificent views of Montego Bay, pleasant tropical breezes, and spectacular sunsets.

Caribbean Villas and Jamaica Villa Rentals

Ocho Rios, Jamaica, 5 bedrooms

To enter the front door of Emerald Seas is to leave the cares of the world behind and enter your own private resort.

Caribbean Villas and Jamaica Villa Rentals

Oracabessa, Jamaica, 9 bedrooms

With an 80% return rate for guests, Golden Clouds is recognized as one of the top villas in Jamaica.

Caribbean Villas and Jamaica Villa Rentals

Discovery Bay, Jamaica, 7 bedrooms

Fortlands Point is a stunning 7 bedroom and 7.5 bath beachfront vacation villa with three private white sand beaches and its very own cove.

Caribbean Villas and Jamaica Villa Rentals

Runaway Bay, Jamaica, 3 bedrooms

Idle Hours Villa is the perfect setting for a family or a couple seeking to escape to their own private relaxing haven.

Caribbean Villas and Jamaica Villa Rentals

Discovery Bay, Jamaica, 4 bedrooms

Located on a private waterfront acre, Sea Haven is a traditional West Indian Cottage dressed in a miracle of colour. 

Caribbean Villas and Jamaica Villa Rentals

Montego Bay, Jamaica, 6+ bedrooms

This incredible 5 acre vacation estate looks across the blue Caribbean Sea to the vibrant city of Montego Bay. 

Caribbean Villas and Jamaica Villa Rentals

Montego Bay, Jamaica, 7 bedrooms

Relax in this incredible 7,000 sq. ft. villa, fully furnished with fine art, antiques, and contemporary style furniture. 

Caribbean Villas and Jamaica Villa Rentals

Montego Bay, Jamaica, 7 bedrooms

Harmony Hill is a private, seven bedroom villa combining Jamaica’s rich architectural tradition with modern, world-class amenities and service. 

Nevis, West Indies, Caribbean, 2-6 Bedrooms

Stretch out in Four Seasons comfort, from spacious guest rooms and suites, to exclusive villa and estate home accommodations.

Pinney's Beach, Nevis, West Indies, Caribbean, 4 Bedrooms

Villa 5 is a luxurious villa built to world class standards.

Villas Caribbean and St. Barts Villas

Grand Cul de Sac, St. Barts, West Indies, 2-3 Bedrooms

Villas Caribbean and St. Barts Villas

Camaruche, St. Barts, West Indies, 3 Bedrooms

Villas Caribbean and St. Barts Villas

Colombier, St. Barts, West Indies, 3 Bedrooms

Villas Caribbean and St. Barts Villas

Lorient, St. Barts, West Indies, 2 Bedrooms

Villas Caribbean and St. Barts Villas

Pointe Milou, St. Barts, West Indies, 2 Bedrooms

Villa Papillon Blanc offers stunning sunsets, views of the St. Barths mountainsides, and St. Maarten.

Villas Caribbean and St. Barts Villas

St. Jean, St. Barts, West Indies, 3 bedrooms

La Maison Rouge is located high on a hillside with a vast panorama of the turquoise water of St. Jean Bay.

Villas Caribbean and St. Barts Villas

Toiny, St. Barts, West Indies, 2 bedrooms

Villa Toiny is an open, spacious villa set on three acres of private grass covered land.

Villas Caribbean and St. Barts Villas

Petite Cul-De-Sac, St. Barts, West Indies, 3 bedrooms

Villa Guillaume is a charming and very private property perched on the heights of Petit-Cul-De-Sac: a peaceful and green area of St. Barts.

Villas Caribbean and St. Barts Villas

St. Jean, St. Barts, West Indies, 3 bedrooms

A perfect location providing a constant caribbean breeze, Les Acajous is a true little paradise for peace and quiet.

Villas Caribbean and St. Barts Villas

Lorient, St. Barts, West Indies, 2 bedrooms

Villa Amore provides beautiful 180 degree views of Lorient and small islands, ideally situated on the top of the hill of Camaruche. 

Caribbean Vacation Homes and St. John Villas

Chocolate Hole Bay, St. John, US Virgin Islands, 3 Bedrooms

Nestled in an exclusive neighborhood, Villa Catalina offers comfort and privacy.

Caribbean Vacation Homes and St. John Villas

Coral Bay, St. John, US Virgin Islands,  5 Bedrooms

Capturing the natural beauty and romance of St. John, VillAllure takes full advantage of the views and breezes while providing maximum privacy in the superbly intimate setting of a fine St. John villa rental.

Caribbean Vacation Homes and St. John Villas

Chocolate Hole, St. John, US Virgin Islands, 5 Bedrooms

Sitting atop the summit of Maria’s Bluff, Kismet encompasses 360° views with every window offering a delight to the eye.

Caribbean Vacation Homes and St. John Villas

Fish Bay, St. John, US Virgin Islands, 4 Bedrooms

Sea Turtle Villa sits high above the crystal blue waters of the Caribbean, on the smallest U.S. Virgin Island of St. John.

Caribbean Vacation Homes and St. John Villas

Coral Bay, St. John, US Virgin Islands, 4 Bedrooms

Coral Rays is a terrific place to relax with lots of outdoor patio space, a large jacuzzi, and a wonderful private pool.

Caribbean Vacation Homes and St. John Villas

Catherineberg, St. John, US Virgin Islands, 5 Bedrooms

Jungle Stone is an ultra luxurious villa overlooking some of the most majestic and breathtaking views anywhere in the world.

Caribbean Vacation Homes and St. John Villas

Peter Bay, St. John, US Virgin Islands, 5 Bedrooms

Coco de Mer, overlooking one of the most beautiful and dramatic ocean views in the world, is one of the Caribbean's most magnificent private villas.

Caribbean Vacation Homes and St. John Villas

Peter Bay, St. John, US Virgin Islands, 5 Bedrooms

From Peter Bay beach, to Cinnamon Bay beach, to Francis and Maho Bay beaches, the North Shore panoramas are simply breathtaking, spectacular, and majestic in this amazing villa.

Caribbean Vacation Homes and St. John Villas

Virgin Grand Estates, St. John, US Virgin Islands, 4 Bedrooms

Visitors of Villa South Palm will enjoy magnificent ocean views from the elegance and privacy of an architectural masterpiece.

Caribbean Vacation Homes and St. John Villas

Maria Bluff, St. John, US Virgin Islands, 4 Bedrooms

Las Brisas is a superbly designed and constructed, distinctively furnished home that was completed in 2002.

Caribbean Vacation Homes and St. John Villas

Catherineberg, St. John, US Virgin Islands, 4 Bedrooms

Villa Peace & Plenty is a new, spacious, 3 level villa with a magnificent view located on St. John's exclusive North Shore.

Caribbean Vacation Homes and St. John Villas

Chocolate Hole Bay, St. John, US Virgin Islands, 3 Bedrooms

Located on top of a mountain, Villa Mar de Amores offers complete privacy and tranquility.

Caribbean Vacation Homes and St. John Villas

Chocolate Hole, St. John, US Virgin Islands, 4 bedrooms

Villa Claudia overlooks the entire south shore of St. John with expansive, panoramic ocean views.

Caribbean Vacation Homes and St. John Villas

Chocolate Hole, St. John, US Virgin Islands, 5 bedrooms

Poseidon's Secret is an elegant Mediterranean style villa with its own private sandy beach and swimmable shoreline.

Caribbean Vacation Homes and St. John Villas

Gifft Hill, St. John, US Virgin Islands, 2 to 5 bedrooms

Located on the peak of Gifft Hill, enjoy the unobstructed and panoramic views and sunsets in this fabulous villa.

Caribbean Vacation Homes and St. John Villas

Peter Bay, St. John, US Virgin Islands, 3 bedrooms plus guesthouse

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