View from your Caribbean villa. Ani Villa, luxury on Anguilla. Casa Lupa villa view from porch. Caribbean villa ocean views. Rockstar Caribbean villa. Saint Barts luxury villa collection. Villa rentals for Caribbean weddings.

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!

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

  • 100 Pond Bay
    Virgin Gorda, BVI
    Take your pick of three pools to relax in while sipping lemonade and looking out at your view!
  • Ani Villa North
    Anguilla
    Ultra Modern Design, a Private Concierge, Take your breath away Sunsets- all at Ani Viilla North on Anguilla
  • Parrot Cay Resort- Tamarind Villa
    Turks and Caicos
    Traveling with a group has never been easier, or more luxurious, with this villa in the midst of a five-star resort

Find Your Caribbean Villa

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