Caribbean Villa Rentals

Know Before You Go...

Miles of magnificent ocean views; secluded private islands; white sand beaches at your doorstep are closer than you think--a click or a phone call away, actually. Whether you want to experience it all, or take a minimalist approach, our island experts have you covered. Choose from luxury villas in Anguilla, Barbados, St. Barts, St. John, St. Lucia and other Caribbean destinations. Many Caribbean villa rentals provide maid service, personal chefs and concierge services!

Beautiful shot from Tortola, British Virgin Islands. Angora Villa Pool from Dining Room Couple on beach in Barbaods Relaxing time on the beach. The beach on St. Martin.

Caribbean Villas

The only thing better than being in a tropical paradise is pretending it's your home. Our Caribbean villa rentals do just that. Live in your own private beach house with the amenities of a hotel or resort. We represent luxury villas in Anguilla, St. Barts, Turks and Caicos, St. John, and many other Caribbean islands. Start browsing. You're sure to find your perfect Caribbean villa rental.

Caribbean Hotels

It's been a long year. You've earned an unbelievable vacation. Don't leave it to chance. Our extensive listings of Caribbean hotels and resorts, restaurants, maps, and photos give you a better understanding of Caribbean destinations like Barbados, St. Lucia, St. Thomas, St. Martin and more. With so many hotel options, you may need to make two trips!

Caribbean Specials

What Travelers Say About WhereToStay.com...

"Miss Shawna is so very helpful and the fact that she personally knows the properties is very valuable to help the client." - Rachel G. "Thank you so much for guiding us through one of the most spectacular vacations of our lives. I could not have imagined a more beautiful trip." - C. Stack "WhereToStay was terrific, especially Shawna who helped reserve the villa, organize transfers, ferry, pre-stocking of the villa. She was fantastic!" - Miranda "Thank you very much for your attention to every detail. It was so smooth and easy for us and for that we are so appreciative." - Mary Lee "Thanks again for the info and the advice...you're always spot on." - Keith

The Caribbean Villa and Hotel Experts

We'll prove it - give us a call!

Knowledge is power - especially with vacation planning. That's why our Know before you go...® philosophy is so vital. We share the prime times for Caribbean travel; offer real travel reviews on Caribbean villa rentals; reveal the best beaches in Anguilla, St. Lucia, Barbados and more. Little convincing is needed when considering a Caribbean vacation. You just want to make the best choice. Our more than 15 years of experience enables us to provide honest, unbiased opinions about Caribbean rentals, restaurants and tourist attractions.

Luxury Villa Rentals & Concierge Services

Our experience and customer service set us apart.

Why not let your vacation begin in the planning stage? Sit back, relax, and let WhereToStay.com's villa rental experts do the legwork for you. It's like having your own personal assistant (you'll have to get your own coffee, though). We'll help find your unique Caribbean getaway. In addition, we'll arrange car rental, meet and greet, grocery pre-stocking, chef services, childcare, spa services, excursions and much more. We leave no grain of sand unturned, so your vacation can begin... well... here!

We Know The Caribbean

Our Focus, Our Expertise

Founded in 1995, WhereToStay.com is the original Caribbean travel review site, providing aspiring vacationers with real travel reviews on Caribbean rentals, restaurants, entertainment and more. Today, WhereToStay.com represents hundreds of Caribbean villas, hotels, private islands and resorts. Our Caribbean villa rental experts have traveled to the islands, stayed in the villas and can help you make the best decision for your unique rental needs. We invite you to explore our site and review our luxury vacation rentals and Caribbean destinations.

Caribbean Blog

Best Of the Caribbean

Caribbean Travelers' Reviews

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