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Dudley Wood Villa

Barbados

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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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!

Celebrate Rum Day With These 7 Caribbean Cocktails

Happy Rum Day from WhereToStay.com! In honor of the day, we've round up our favorite seven cocktail recipes. What do they have in common? You guessed it: rum.

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Top 10 St. Barts Villas

St. Barts is known as a luxurious getaway for rockstars, supermodels, actors, and professional athletes. The island offers fine cuisine, designer boutiques, hot nightclubs, and art galleries; but, it’s also a family-friendly spot with water sports, casual dining, and ...

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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. At WhereToStay, we want to help you find the perfect vacation rental for your Caribbean getaway. To make your planning process easier, here’...

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