WhereToStay - Your Global Villa Experts

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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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.

Italian Lakes villas

Italian Lakes

Vast alpine vistas, glossy waters and bougainvillea-veiled towns - Lake Como boasts an allure that has endured since wealthy Romans first visited these restorative shores. Be beguiled by the most opulent of villas, century-old pastel pillars sinking into the shores…


Dominican Republic villas

Dominican Republic

Nestled between Puerto Rico and Cuba on an island that it shares with the Republic of Haiti, the Dominican Republic offers travelers the best that the Caribbean has to offer, with a unique personality rooted deeply in her Latino heritage.…


Algarve villas


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…


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…


Cote d'Azur villas

Cote d'Azur

While the world’s glitterati descend on Cannes in the spring, this glamorous seafront spot is at its best in the height of the fabulous French summer. Overlook sparkling mega-yachts moored in the curve of La Croisette from your elaborate belle-epoque…


Croatia villas


Why not 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…


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…


Anguilla villas


If your heart is set on getting away from it all and experiencing a true island escape, Anguilla, with its friendly people and natural attractions, is a perfect choice. Its low lying, arid terrain doesn't leave much in the way…


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Basking in French Riviera Glory: A Deep Dive into the Côte d'Azur’s Quintessential Destinations

Andrew - 23 Apr 2024

Basking in French Riviera Glory: A Deep Dive into the Côte d'Azur’s Quintessential Destinations

The French Riviera, or Côte d'Azur where luxury, history, and breathtaking beauty dance together in perfect harmony. It's not just a destination; it's a lifestyle, darling! Each stop along the dazzling Côte d'Azur tells its own fabulous tale, ...

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Maho Crossroads on St. John - Spend a day at the Best Beach Bar in the Caribbean!

Andrew - 06 Feb 2024

Maho Crossroads on St. John - Spend a day at the Best Beach Bar in the Caribbean!

Maho Crossroads, nestled on St. John in the US Virgin Islands and just a stone's throw from the mesmerizing Maho Bay, has been honored as the #1 Beach Bar in the Caribbean for 2024 by the Caribbean Journal. This accolade, awarded for ...

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