Villa Articles

Posted on Dec 11, 2019

Best Cayman Island Villas of 2019

The Cayman Islands are a beloved location for ocean-lovers for good reason: Grand Cayman is known as one of the top-rated scuba diving locations in the world! Coral reefs, shipwrecks,…

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Posted on Nov 24, 2019

Our Favorite Villas and Restaurants on Barbados

Barbados’s Platinum Coast is known for its amazing white sand beaches, luxurious staffed villas, and unique fusion cuisine. This island’s fun, friendly, and safe environment has something for everyone. At…

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Posted on Nov 19, 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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Posted on 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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Posted on 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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Sandy Lane Beach Club
Sandy Lane Beach Club
Posted on Aug 23, 2019

A Barbados Beachfront Villa Experience Without the Premium

The best part of any Caribbean vacation is the beach, but

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Find the perfect villa for your next family vacation!
Find the perfect villa for your next family vacation!
Posted on 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!
Posted on 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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Posted on 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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Posted on 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

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