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Others' claim to be Caribbean experts. We prove it. Every call. Every email, Every chat.

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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

  • Ani Villa Estate
    Anguilla
    Huge luxury estate features 2 separate villas, a full staff, and incredible ocean views
  • Turtle Tail Estate
    Turks and Caicos
    Turtle Tail Estate: a secluded, high-end Provo beach house that boasts fantastic amenities and over 4 tropical acres of land!
  • Bon Temps Villa
    St. Barts
    Gorgeous six-bedroom villa offers spacious accommodations, unbelievable views, and privacy for a dream vacation

Find Your Caribbean Villa

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