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 741 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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We work directly with owners and local partners to offer the best prices, providing exceptional value and personalized service for a seamless, cost-effective booking experience.

Global Getaways

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

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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Italian Lakes villas

Italian Lakes

The Italian Lakes, located in northern Italy, are renowned for their stunning landscapes, clear waters, and picturesque towns. Lake Como, Lake Garda, and Maggiore are the most famous, each offering its own unique charm. Lake Como is celebrated…

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St. Lucia villas

St. Lucia

The first thing visitors to St. Lucia will notice is how exotically green it is. The 238-square-mile island is dotted by protected parklands that preserve its lush foliage, which serves as home to parrots, wild birds and a range of…

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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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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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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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Croatia villas

Croatia

Escape to the Adriatic coast to experience Croatia - the ideal luxury destination for families and groups of friends. Explore the delights of the Dalmatian coastline. Croatia has so much to offer, from crystal clear waters, sailing opportunities, fresh Mediterranean cooking and a…

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Mansions

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Jean - 11 Jul 2025

Summer in Iceland: Midnight Sun Magic & Wild Luxury Adventures

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Jean - 11 Jul 2025

Iceland Winter Wonderland: Northern Lights, Ice Caves & Cozy Escapes

Iceland Winter Wonderland: Northern Lights, Ice Caves & Cozy Escapes Best time to go: November–March Why go: Northern Lights, snow-dusted landscapes, and wild winter adventures, all wrapped in world-class luxury. Iceland in winter is pure magic. Step into a shimmering ...

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