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Your Villa Concierge helps you find the right island, the perfect villa, beginning to end. Your personal villa expert!

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Our top priority is your experience. We are not commission based, so you'll get unbiased advice. As a result, WhereToStay has a Shopper Approved rating of 5.0/5 based on 409 ratings and reviews.

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Osprey is located on the ocean side of Chalk Sound

Osprey Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

CARIBBEAN VILLAS

Whatever experience you're looking for, we have an expert for you. Your dedicated Villa Expert will work with you from start to finish—from choosing the perfect Caribbean island and luxury Caribbean villa to sharing all the best spots to eat, shop, and play. Let's get started!

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GET INSPIRED!

One of the best parts of traveling to the Caribbean is sharing your adventures. So, we started our Caribbean blog. Read our stories and get inspired for your trip!

Why Now is the Perfect Time to Plan Your Next Vacation
Why Now is the Perfect Time to Plan Your Next Vacation

Stuck at home? Plan your escape! Most of us have more time on our hands than ever, so make the most of it by giving yourself something to look forward to! Whether you’re planning to travel with relatives who ...

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Caribbean Vacation Villas Offer Great Value!
Caribbean Vacation Villas Offer Great Value!

Vacations are all about creating memorable experiences and some of the best are made in a private villa in the Caribbean. It’s achievable for all budgets even on some of the most prestigious islands. Our Caribbean villa experts can ...

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The Most Romantic Villas in the Caribbean
The Most Romantic Villas in the Caribbean

Hit the refresh button on your relationship and make some memories in the Caribbean! Planning a romantic getaway is ripe with high expectations: you want beauty, privacy, and luxury… all within your budget. There are thousands of villas on the ...

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