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Luxury Villas in Tuscany

Find Your Extraordinary

Tuscany Villa Holiday

Tuscany captures everything we love about an Italian escape. 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 simplicity and flavour. Hilltop villages dot the landscape, encouraging unhurried days and long evenings.

Our collection of villas with pools in Italy is perfectly suited to experiencing Tuscany at its most relaxed. These beautifully characterful homes offer privacy, space and the pleasure of having your own pool to retreat to after days spent exploring. They’re also ideal for family-friendly escapes, with generous gardens, flexible layouts and locations that make travelling with children feel wonderfully easy. It’s a way to enjoy Tuscany that’s as comfortable as it is memorable — best enjoyed from an Oliver’s Travels villa.

Why stay with us?

Style and character sit at the heart of everything we do, and our handpicked villas in Tuscany reflect that beautifully. Each home is chosen by our destination experts, who know every region inside out and seek out places that feel truly special.

And once you’ve found your perfect villa, our Concierge Service is here to take care of the rest. From a fridge stocked for your arrival to private chefs, housekeeping and tailored experiences, think of them as all things planning and recommendations, ready to make your Tuscan escape extraordinary.

Top Regions 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 the good life. Today, visitors come for the same reasons: rolling hills brushed with vineyards, a beautiful stretch of coastline and a pace that encourages you to slow down and savour.

Food and wine sit at the heart of daily life here. 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, the temptation to linger is strong. Coastal seafood, mountain specialities and intimate tastings with local producers make every meal an experience. To explore further, our Tuscany travel guide delves into the region in more detail, including ideas for travelling with children or as part of a group.

What Oliver loves

Springtime in Tuscany, when the hills turn vivid green and the air feels fresh and full of promise. Add a glass of local Chianti at sunset and it’s hard to imagine anywhere better.

At a glance

  • Tuscany boasts seven UNESCO sites – Florence, Siena’s medieval centre, the Leaning Tower, San Gimignano, Pienza, Val d’Orcia, and the 12 Medicean Villas.

  • Dante’s ‘Divine Comedy’ proved so popular throughout Italy that it resulted in the Tuscan dialect being adopted as the country’s ‘standard tongue.’

  • Head to the beach and the Etruscan Coast for some relaxing down-time. The coast combines town-based beaches and super-secluded spots, so there’s something for everyone.

  • Enjoy Tuscany’s famous rolling hills and get involved with day-to-day rural life. Olive picking, pig-feeding and horse riding are all on the cards when you head to the countryside.

  • Florence is perfect for art-lovers, where you can find pieces by Michelangelo, Botticelli and Da Vinci

  • You can’t visit Tuscany without paying a visit to at least one of the local vineyards and sampling some of their delicious vinos

Towns and Villages in Tuscany

Our collection of villas in Tuscany allow you to truly soak up the rural beauty of the region, with our destination experts handpicking them for their proximity to local activities: wine-tasting, walking, hiking, and golfing.

If you want to be close to the main towns, discover these villas close to villages.

Oliver's Hidden Gem

If one town could sum up the beauty, history, and splendour of Tuscany’s iconic towns and villages, we’d say it was Pitigliano. Set atop an intimidating stone cliff, the cobblestone streets wind their way up past intriguing synagogues to the town’s beating heart, Piazza Garibaldi.

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

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

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.

Top Tips

  • Public transport services are likely to operate heavily altered schedules on Sundays. In many rural areas, it may not operate at all. This makes careful planning essential.

  • While travel between the region’s cities and major towns is facilitated by modern highways, many rural areas are serviced by small country lanes and the occasional gravel track. This means it’s good practice to always factor in a little extra travel time when travelling to the countryside.

Getting around Tuscany

Tuscany is well connected and easy to explore, particularly if you want the freedom to roam.

By plane

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

By car

Hiring a car is the best way to experience Tuscany fully, especially if you’re staying in the countryside or plan to explore smaller towns and the coast.

By train

Affordable and reliable between major cities, trains are a good option if you’re keeping travel simple.

By bus or taxi

Buses and taxis are useful in towns and cities, though services can be limited in rural areas — advance planning is key.

By bicycle

For confident cyclists, Tuscany’s countryside offers unforgettable routes through vineyards, valleys and rolling hills, with options suitable for families and more adventurous riders alike.

From the blog…

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