Caribbean Villa Rentals

The Caribbean Villa Experts

We make it easy to find a Caribbean villa rental that's perfect for you. Just use our villa search feature to pick a Caribbean location, number of bedrooms, price range and choice of a pool, beachfront villa or rentals near the beach. We represent all of the top vacation rentals in destinations like Anguilla, St Lucia, Barbados and St. Barth's. Browse through our luxury villa rentals or simply call us and speak to an expert on Caribbean villa rentals!

Find your Villa

Pool Beachfront
AC Short Walk to Beach

Why Rent with Us?

For two decades, we have helped travelers with their Caribbean dream vacations. Whether you are seeking a Caribbean destination wedding, honeymoon, family trip or simply a private island getaway, we are your Caribbean villa rental experts. Unlike many owners and mangers who represent only a handful of villas, we represent villas all throughout the Caribbean and provide honest and unbiased opinions. But don't just take our word for it, WhereToStay.com client reviews—good or bad—assure you are making the most informed decision! Our staff also work hard to be sure that you get the best possible deal!

Concierge Services

Vehicle rentals with trusted suppliers
Arrange to have your villa rental pre-stocked with groceries
Hire a personal chef to prepare your meals for you
Arrange for a wide range of spa services
Coordinate weddings, reunions and other special events

Our Favorite Villas

St. Bernard's Hill House
Tortola, BVI
Long Bay Beach House
Turks and Caicos
Long Bay Beach House: Brand new villa right on Providenciales' coveted Long Bay Beach.
Villa D-3 at Tortuga Bay
Dominican Republic
minutes to the white sand beach and golf!
Twin Palms Villa at Tryall
Jamaica
Twin Palms: Fabulous pool spread out over seven levels will make you feel like you have a resort all to yourself
Bajacu
Turks and Caicos
Luxury abounds at the gorgeous Bajacu Villa : a sprawling retreat on the island of Providencialies.

Caribbean Villas for Weddings & Special Occasions

Planning a Caribbean wedding? How about a romantic honeymoon getaway? Maybe a Caribbean family vacation or reunion? Possibly a couples vacation, group vacation or private island? The Caribbean offers something for everyone. Check out our featured topics section below to find villas that are perfect for that special occasion!

Wedding Villas

Honeymoon Villas

Let our villa rental experts guide you...

...to your best villa rental experience! Our team of experts have over 20 years of experience in Caribbean villa rentals and can identify the best-suited villa rentals for you. Check out some of our favorite villas below or simply call us and let one of our island experts assist you in finding your ideal villa! Our goal at WhereToStay.com is to make you a client for life. We have well seasoned Caribbean villa rental experts for each island who know the villas and sincerely care about helping you make the absolute best choice.

Caribbean Villa Concierge

You're not only getting the best advice when renting a Caribbean villa with WhereToStay.com, but you also benefit from our expertise and knowledge of the islands—where to eat, where to shop and what to do. From the services we provide—such as coordinating your arrival, arranging car rental, spa and chef services, to villa rental provisioning and island excursions—you will feel confident and prepared before you ever leave home. Let us guide you from start to finish, giving you only honest and unbiased opinions and suggestions along the way.