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Pool and backyard facing Great Cruz Bay at Ardisia Villa

Ardisia Villa

Great Cruz Bay, St. John

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!

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!

Best Turks and Caicos Beachfront Villas of 2018
Best Turks and Caicos Beachfront Villas of 2018

Turks and Caicos is home to the Caribbean’s most beautiful beaches and most luxurious villa rentals. Turks and Caicos villas are the best of the best, and there’s several options for every budget and style. At WhereToStay, we ...

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Vacation Hacks: Travel Insurance Edition
Vacation Hacks: Travel Insurance Edition

If you’ve recently booked a vacation to the Caribbean, you’re likely in the midst of planning and preparing. Whether you’re shopping for the perfect swimsuit, scouting out the most exciting attractions, or setting up a romantic evening ...

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Why You Need to Visit the Cayman Islands
Why You Need to Visit the Cayman Islands

The Cayman Islands are the sapphires of the Caribbean. Turks and Caicos and St. Barts may be the best-known and most glittery, but Cayman shines in its own way. The Cayman Islands are a trio of lovely, unspoiled islands with ...

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