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Sep 9, 2019

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…

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Find the perfect villa for your next family vacation!
Find the perfect villa for your next family vacation!
Jun 7, 2019

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,…

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Fresh cocktails prepared by your own bartender!
Fresh cocktails prepared by your own bartender!
Feb 18, 2019

Best Staffed Villas in the Caribbean

The only thing better than staying in a Caribbean villa is staying in a staffed Caribbean villa. After all, who really wants to cook on vacation? Some travelers like the…

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Oct 30, 2018

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…

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Sep 19, 2018

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,…

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Aug 3, 2018

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…

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Jul 24, 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. At WhereToStay, we want to help you find the perfect vacation rental for your…

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Mar 15, 2018

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…

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Don't lift a finger on vacation!
Don't lift a finger on vacation!
Oct 25, 2017

How to Feast Like Royalty in the Caribbean

On our last trip to Turks and Caicos, Shawna and I stayed at Hesperides House on Taylor Bay. There are so many things I love about that house, but one…

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