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Caribbean Villas

  • Destinations: 17
  • Villas: 1248
  • Private Islands: 7

Escape to the Islands

Our Caribbean villas feature pristine beachfronts, private pools, and spacious outdoor living spaces where you can enjoy the islands' year-round sunshine.  Whether you're looking to hide away with your special someone on a secluded beach, take the entire family on a water sports adventure, indulge in gourmet Caribbean cuisine, or tee off on the world's most beautiful golf courses, there is an island that is perfect for you. And with a portfolio of over a thousand luxury villa rentals throughout the Caribbean, we're sure to match you with a villa that is just what you're looking for.

All Caribbean Destinations

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Caribbean Overview

Not sure which Caribbean destination is right for you? Here's a quick breakdown.

Anguilla:  A tiny 15-mile island with spectacular white-sand beaches. Perfect for those seeking privacy, tranquility, and stunning natural beauty.

Antigua: Most of our villas are located in the exclusive Jumby Bay Resort, set on a 300-acre private island located 2 miles off the coast of Antigua and accessible only by boat.

Bahamas: The 700 islands that make up the Bahamas offer pink- and white-sand beaches and crystal-clear turquoise water perfect for water sports.  Intra-island flights, ferries, and yachts allow visitors to island-hop.

Barbados: A limestone-coral island with spectacularly clean, soft, often pink-tinged sand. Most of our villas in Barbados come with a full staff consisting of a chef, butler, housekeeper, and laundress.

Dominican Republic: The Dominican Republic offers a rich fusion of Latin American, Spanish, French, and British influences. Many of our Dominican villas are located in Casa de Campo, an award-winning luxury resort with one of the world’s best golf courses.

Grenada: Known as the "Spice Island" for its production of nutmeg, clove and cinnamon. The island’s capital, St. George's, is hailed as one of the most picturesque harbor towns in the Caribbean.

Jamaica: Perfect for both family fun and romantic retreats. Jamaica has it all: gorgeous beaches, natural beauty, and unbeatable cuisine.  Most villas in Jamaica come with a full staff consisting of a chef, butler, housekeeper, and laundress.

St. Barts: Gourmet French food, upscale shopping, and quaint, storybook-style architecture make St. Barts a favorite for travelers looking for an air of elegance.

St. Croix: St. Croix is both the largest and the most remote of the U.S. Virgin Islands. Its exceptionally diverse terrain – mountains, rolling pastures, rainforest, and beaches – offers visitors plenty to explore.

St. John: The smallest and greenest of the U.S. Virgin Islands, St. John is perfect for nature lovers.  The Virgin Islands National Park takes up 60% of the island and offers spectacular hiking trails to pristine, undeveloped beaches.

St. Lucia: St. Lucia’s dramatic landscape leaves a strong impression; the majestic Pitons tower nearly 3,000 ft. above the sapphire sea, creating a stunning backdrop from every angle. The island is also home to the world’s only drive-in volcano.

St. Martin: A unique destination for its dual identity: The island’s northern collectivity (St. Martin) is governed by France, while its southern territory (St. Maarten) is governed by the Netherlands. The French side offers gourmet cuisine and fashionable shopping, while the Dutch side offers fantastic nightlife and a more casual atmosphere.

St. Thomas: The U.S. Virgin Islands’ most populated island offers the widest variety of attractions, from the USVI’s vibrant capital of Charlotte Amalie to heavenly white-sand beaches.

Tortola: As the capital island of the British Virgin Islands, Tortola serves as its commercial and business center, offering a great variety dining, nightlife, and resort options. Quieter, more remote parts of Tortola offer solitude for the escapist.

Turks & Caicos: Over 40 islands make up this tropical archipelago, only 8 of which are inhabited. Providenciales – also known as Provo – is home to Grace Bay Beach, consistently voted the best beach in the world.

Virgin Gorda: This island gem in the British Virgin Islands has remained uncommercialized and pristine, attracting honeymooners and privacy-seekers the world over. The island's most famous landmark is The Baths, a beach made up of giant granite boulders that form hidden pools and grottos.