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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 272 ratings and reviews.

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Impressive views of the Caribbean from the pool and deck area at Island Rider Villa

Island Rider Villa

Rendezvous 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!

Tipping in the Caribbean: An Island by Island Guide
Tipping in the Caribbean: An Island by Island Guide

Tipping can be one of the trickiest parts of travel— some regions won’t accept tips at all, whereas others will tack on additional fees until you’re bone-dry. The Caribbean is made up of several different cultures and islands, ...

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Best Things to Do in the Cayman Islands
Best Things to Do in the Cayman Islands

My husband, Steve, and I just got back from a trip to Grand Cayman, and we couldn’t resist sharing our favorite places with you. This list has some trusted treasures and some brand-new spots, with something for everyone. Enjoy!

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Necker Island is Back!
Necker Island is Back!

We’re excited to announce that the ultimate private getaway, Necker Island, is reopening for rental October 2018. Necker is a gem in the British Virgin Islands that’s hosted rock stars, royalty, and every other celebrity in between. It's also ...

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