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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 360 ratings and reviews.

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Ananda Villa photo

Ananda Villa

Pointe Milou, 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 Beach Club in Barbados
The Best Beach Club in Barbados

The best part of any Caribbean vacation is the beach. Nothing beats a day lounging on the warm sand, breathing in the salty air, and jumping into the crystal clear sea. Available beachfront villas are hard to find though, especially ...

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Where To Eat in St. Barts
Where To Eat in St. Barts

“People who love to eat are always the best people.” - Julia Childs The Caribbean is my happy place for so many reasons: the beaches, the people, and without a doubt, the food. Island cuisine is always inventive, and it’...

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8 Best Family Vacation Villas in St John
8 Best Family Vacation Villas in St John

St. John is one of the quieter gems of the Caribbean. This U.S. Virgin Island's lush, rolling hills and turquoise seas sparkle just as much as Turks or St. Barts, but the pace is just... a little... slower. If ...

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