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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!

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

  • Mare Blu Villa
    St. John
    Families or active couples will find every need met at Mare Blu Villa on Rendezvous Bay
  • Sol y Sombra
    Virgin Gorda, BVI
    A separate guest cottage makes this location ideal for several travelers who want to dwell independently.
  • Twin Palms Villa at Tryall
    Twin Palms: Fabulous pool spread out over seven levels will make you feel like you have a resort all to yourself

Find Your Caribbean Villa