YOUR PERSONAL CARIBBEAN VILLA EXPERTS!

GOOD SAND ADVICE

Caribbean Villas

Personal Touch

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

Villa Experts since 1995

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 379 ratings and reviews.

Personally Inspected villas.

Verified Villas

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

Best rates guaranteed

The Best Price

  • No credit card fees
  • No commission charges
  • Absolutely no hidden fees

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

Shopper Approved

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!

Best Cayman Island Villas of 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, and diving walls fill the sea around the Cayman Ridge, ...

more

Our Favorite Villas and Restaurants on Barbados
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 WhereToStay, we’re dedicated to helping you find ...

more

Best Anguilla Villas of 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 hotels, and villas, yet the island exudes a carefree, barefoot ...

more

Where To Stay

Home Page
My Trip
My Favorites
Magazine