Luxury Articles

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Nov 13, 2019

Best Anguilla Villas of 2019

Anguilla is known first and foremost for its white sand beaches, great restaurants, and friendly locals. This small, quiet island has an authentic Caribbean feel. There are top-notch restaurants, luxury…

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Nov 5, 2019

St. Martin’s Hottest Luxury Villas

St. Martin is one of the lesser known gems of the Caribbean, and even the most seasoned travelers are sure to find new things to enjoy on this French-Dutch island.…

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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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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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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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