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

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

  • Kismet Villa
    St. John
    Kismet: 360 degree views of sunrise and sunset from atop Maria's Bluff.
  • Cove Spring
    Barbados
    A fully equipped gym, a staff of 12, and a theater that seats 20 sets this island estate apart from the usual vacation villa
  • African Sapphire Villa at Altamer
    Anguilla
    Off-The-Charts Upscale Living: you've found one of Anguilla's most sought-after private villas!

Find Your Caribbean Villa

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