Luxury Villas in Tuscany

Tuscany Villa Holidays

Tuscany captures everything we love about an Italian villa holiday. Sun-warmed hills ripple with vineyards and olive groves, a rich artistic heritage shaped by the Renaissance and medieval eras, and a food culture built around seasonal flavours.

Our collection of villas with pools in Italy is perfectly suited to experiencing Tuscany. These characterful homes offer privacy and space, with the added pleasure of a pool. They’re also ideal for family-friendly escapes, with generous gardens, flexible layouts and locations that make travelling with children feel wonderfully easy.

Why stay with us?

Style and character are central to every Oliver’s Travels stay, and our villas in Tuscany are no exception. Our destination experts know the region’s hill towns, wine country and coast inside out, handpicking homes for their setting, privacy and access to the best of Tuscany. Once you book a holiday, our Concierge Service is here to help with planning and recommendations to make your stay truly extraordinary.

Top Regions in Tuscany

Florence

Florence

69 Villas
Chianti

Chianti

50 Villas
Lucca & Pisa

Lucca & Pisa

48 Villas
Arezzo

Arezzo

42 Villas
San Gimignano

San Gimignano

25 Villas
Montepulciano

Montepulciano

18 Villas
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Luxury Villas in Tuscany

Why Visit Tuscany?

Tuscany has been captivating travellers for centuries. From Roman settlers drawn to its fertile land to Renaissance masters inspired by its beauty, this is a region shaped by art, history and an enduring love of la dolce vita. Today, visitors come for the same reasons; its rolling hills covered with vineyards, a beautiful stretch of coastline and a pace that encourages you to slow down.

Food and wine sit at the heart of daily life. Tuscany’s rich soil produces exceptional ingredients, from peppery olive oil and prized truffles to the famous bistecca alla Fiorentina. The Chianti wine region needs little introduction, offering some of Italy’s most celebrated vintages, best enjoyed at the vineyard itself.

Despite its reputation, Tuscany never feels overwhelming. Beaches, countryside and culture sit comfortably side by side, making it an easy, rewarding destination for couples, groups and families alike. Florence is a highlight, romantic, vibrant and wonderfully walkable, with world-class museums, lively markets and masterpieces by Michelangelo, Botticelli and Leonardo da Vinci.

For food lovers, there is plenty beyond Chianti too, with coastal seafood, mountain specialities and tastings with local producers offering a different side of Tuscany wherever you stay.

Destinations in Tuscany

Montepulciano

Montepulciano

Wine connoisseurs will want to take a trip to Montepulciano, which shares its name with one of the country’s most popular red grapes. While the surrounding area is covered in vineyards, the town itself offers a fascinating insight into the region’s history. The central Piazza Grande is a must-see and a glittering jewel atop a beautiful crown of a town.

Lucca

Lucca

Though smaller than Tuscany’s second city, Siena, Lucca makes up for its diminutive size with bucket-loads of charm. Visitors can walk around the city’s 16th-century walls, relax on the tree-topped Guinigi Tower, or people-watch in the lively Piazza dell’Anfiteatro. Those visiting Tuscany on a family holiday will enjoy the playgrounds and picnic areas just outside the city walls.

Florence

Florence

With its world-class art collections, unparalleled architectural beauty, and vibrant café and restaurant scene, you could spend weeks exploring the wonders of Florence. Whether you want to check out the San Lorenzo Market, visit the Duomo, or just wander the streets, you’ll have a cracking time.

Getting Around

Fly into Florence or Pisa, both offering excellent international and European connections and convenient access to the region.

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