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Your Villa Concierge helps you find the right island, the perfect villa, beginning to end. Your personal villa expert!

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Our top priority is your experience. We are not commission based, so you'll get unbiased advice. As a result, WhereToStay has a Shopper Approved rating of 5.0/5 based on 371 ratings and reviews.

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If we wouldn't stay there, then you shouldn't either! Our "Verified" villas are hand-selected, meeting our high standards.

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Private waterfront pool at Ecoute les Vagues

Ecoute les Vagues

Flamands, St. Barts

CARIBBEAN VILLAS

Whatever experience you're looking for, we have an expert for you. Your dedicated Villa Expert will work with you from start to finish—from choosing the perfect Caribbean island and luxury Caribbean villa to sharing all the best spots to eat, shop, and play. Let's get started!

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GET INSPIRED!

One of the best parts of traveling to the Caribbean is sharing your adventures. So, we started our Caribbean blog. Read our stories and get inspired for your trip!

The Best Beer in Turks and Caicos
The Best Beer in Turks and Caicos

The best way to experience the Caribbean is to use all five senses to soak up the islands: touch, sight, sound, smell, and TASTE. Each island has its own specific culture, especially Turks and Caicos. The Turks and Caicos Islands ...

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Why WhereToStay is the Best Way to Book Your Caribbean Vacation
Why WhereToStay is the Best Way to Book Your Caribbean Vacation

Your vacation is the most important week of your year. When it comes to booking a vacation rental, the research can seem overwhelming. There are thousands of islands in the Caribbean, and dozens of those islands have gorgeous rental properties ...

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A Barbados Beachfront Villa Experience Without the Premium
A Barbados Beachfront Villa Experience Without the Premium

The best part of any Caribbean vacation is the beach, but beachfront villas are hard to find, especially on islands as popular as Barbados. The Sandy Lane Beach Club is a luxurious, members-only perk that totally elevates any Barbados experience. ...

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