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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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.

St. Barts villas

St. Barts

Small, pristine and deliberately uncrowded, St. Barts--officially St. Saint Barthelemy--is as European as it gets in the Caribbean. Known as the "Cannes" of the islands for its chic, trendy attitude, deluxe accommodations and the scores of celebrities who frequent her,…

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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.…

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Greece villas

Greece

Head to Mykonos for a hedonistic combination of Hollywood glamour and seductive scenery, where you’ll find the same carefree vibe that attracted the summering starlets of the sixties. Or step back in time through Crete’s many treasures, her depth of…

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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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Turks and Caicos villas

Turks and Caicos

Located in the southeastern Bahamas, Turks and Caicos boasts crystal-clear turquoise waters, powdery white sand beaches, and lush tropical landscapes. Start your day by diving into the vibrant underwater world, home to colorful corals, exotic fish, and even shipwrecks. Or,…

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Anguilla villas

Anguilla

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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Provence villas

Provence

Whether you’re gazing over rolling rural scenery or strolling fields striped with sunflowers and vines, this diverse landscape provides an irresistible taste of rural France at its finest. Well-heeled Parisians and artists alike have long flocked to this idyllic region,…

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Luxury Rental
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Mansions Villas

Mansions

Castles Villas

Castles

Chateaux Villas

Chateaux

Villas Villas

Villas

In-Resort Villas Villas

In-Resort Villas

Private Islands Villas

Private Islands

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Get inspired!

Traveling is all about sharing experiences and adventures, which is why we launched our travel magazine. Dive into our stories and find inspiration for your next trip!

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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