Casa Lupa villa view from porch. Ani Villa, luxury on Anguilla. View from your Caribbean villa. 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

  • Sand Club on Flamands Bay
    St. Barts
    Incredible beachfront villa has a unique and open floor plan along with tons of extras for indoor/outdoor living
  • Sandyline Villa
    St. Martin
    Sitting poolside takes on a whole new meaning at Sandyline Villa-the ultimate vacation getaway!
  • L'Oasis Villa
    St. Martin
    On Baie Rouge Beach, L'Oasis Villa offers instant beach access with sporting activities nearby

Find Your Caribbean Villa

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