WhereToStay - Your Global Villa Experts

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Surf, scuba, scrabble, festival, family time, honeymoon, sight-see... whatever experience you are after, discover our collection of holiday villa rentals perfect for you

Expert Advice for Exceptional Stays

Caribbean Villas
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Our global travel experts help you find the perfect villa, complimented by a tailor made experience made possible by our personal client services team, beginning to end.
Villa Experts since 1995
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Our top priority is your experience. Our unbiased sales advice and personalized client services have earned WhereToStay a 5.0/5 Shopper Approved rating from over 711 reviews.
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If we wouldn't stay there, then you shouldn't either! Our "Verified" villas are hand-selected, meeting our high standards.
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Global Getaways

Explore available locations and reach out to initiate the process of crafting your unique and exciting journey.

St. Barts villas

St. Barts

St. Barths is a Caribbean icon, renowned for its pristine beaches, chic ambiance, and understated luxury, making it the ultimate destination for a villa vacation. Located in the French West Indies, this exclusive island offers a perfect blend of relaxation,…

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Cote d'Azur villas

Cote d'Azur

The Côte d'Azur, or French Riviera, is a glamorous and captivating destination along the southeastern coast of France, known for its stunning Mediterranean coastline, luxurious resorts, and vibrant cultural scene. This sun-drenched region is a haven for those seeking elegance,…

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Dominican Republic villas

Dominican Republic

The Dominican Republic is a Caribbean treasure, renowned for its white-sand beaches, turquoise waters, and vibrant culture, making it an exceptional destination for a luxury villa vacation. This sun-soaked paradise offers the perfect balance of relaxation and adventure, ideal for…

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Balearic Islands villas

Balearic Islands

From fun-loving Ibiza, where the cool, cosmopolitan set summer, to low-key luxury in Menorca, the Balearic islands are the epitome of Mediterranean chic. Whether you come for relaxation or revelry, Ibiza boasts both a barefoot bohemian vibe to the north…

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Turks and Caicos villas

Turks and Caicos

Turks and Caicos is a tropical paradise, renowned for its pristine white sand beaches, turquoise waters, and understated luxury, making it an ideal destination for a villa vacation. This stunning archipelago of 40 islands and cays offers a serene escape…

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Algarve villas

Algarve

The Algarve is a treasure trove for beach lovers, with its dramatic cliffs, crystal-clear waters, and golden sands. Whether you want to relax and soak up the sun, or indulge in thrilling water sports, the Algarve has it all. Take…

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Tuscany villas

Tuscany

From rolling vine-laced hills cloaked in early morning mist, to the art-rich cities that birthed the Renaissance, Tuscany’s tranquil landscapes offer an unforgettable taste of quintessential Italy. Whether you come for a city-break or countryside escape, you’re sure to be…

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Amalfi Coast villas

Amalfi Coast

This stylish stretch of coast is Italy at its most iconic. Pastel-painted houses perch precariously atop vertiginous cliffs, tumbling down into the Tyrrhenian Sea. From Sorrento to Salerno, this celebrated coastline has been the darling of the world’s jet set…

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Exclusive Villas

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Chateaux

Private Islands Villas

Private Islands

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Castles

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In-Resort Villas

In-Resort

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Get inspired!

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Experience the Best of Algarve Golf with Stunning Courses and Luxe Retreats

Christina - 15 Jan 2025

Experience the Best of Algarve Golf with Stunning Courses and Luxe Retreats

If you’ve ever dreamed of combining your passion for golf with sun-soaked luxury, the Algarve in Portugal is calling your name. This is no ordinary golf destination—this is where the world’s elite tee off against a backdrop ...

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5 Must-Experience Summer Festivals in the Algarve: Where Luxury Meets Local Charm

Christina - 15 Jan 2025

5 Must-Experience Summer Festivals in the Algarve: Where Luxury Meets Local Charm

The Algarve is famous for its golden beaches, glamorous resorts, and lavish villas, but did you know it also has a summer festival scene that will make your trip extraordinary? There you can sip fine wine while the sunset sets ...

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