YOUR PERSONAL CARIBBEAN VILLA EXPERTS!

Search Villa Names

GOOD SAND ADVICE

Personal Touch

Your Villa Concierge helps you find the right island, the perfect villa, beginning to end. Your personal villa expert!

We Work For You

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 279 ratings and reviews.

Verified Villas

If we wouldn't stay there, then you shouldn't either! Our "Verified" villas are hand-selected, meeting our high standards.

The Best Price

No credit card fees
No commission charges
Absolutely no hidden fees

Leana Villa

Colombier, St. Barts

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!

WHAT TRAVELERS SAY ABOUT US

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 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, ...

more

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!

more

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 ...

more