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 266 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

Sand Dollar Estate

St. Thomas, USVI

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!

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.

more

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 ...

more

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’...

more