Luxury Villa Rentals In Tuscany

Our luxury villas in Tuscany are the very best you can find, hand-picked by our team of Italian villa specialists. 

Villa holidays in Tuscany combine opportunities for both relaxation and discovery. Explore picture-postcard hill towns, go wine tasting or truffle hunting, returning to your peaceful hideaway with private pool to bask in stunning views of rolling vineyards and olive groves. Dine out in local trattorias, or allow a private chef to prepare fine regional cuisine from the comfort of your villa.

We have an extensive portfolio of luxury Tuscan villas with pools, tennis courts, chefs and housekeepers. In our properties near Florence, a day exploring the world class galleries can be followed by pool relaxation and dining alfresco. In the untamed hills of Chianti, we offer ancient stone farmhouses magnificently restored into private homes. In the Val d'Orcia, choose from a selection of honey-hued farmhouses that have been lovingly converted into Tuscan luxury villas, located within easy reach of noted wine towns.

Whatever you have been dreaming of for your Tuscan escape, our knowledgeable team are on hand to find the perfect villa for you.

THE SEASON AHEAD

Right now, Tuscany is still glowing in the summer sunshine. Rows of cypress trees cast long shadows across golden fields. Medieval hill towns rise against vivid blue skies. Warm evenings drift by over glasses of wine in village squares. But autumn is not far away, and it is a season I always look forward to.

For one thing, visiting Tuscany in autumn means you can enjoy cultural treasures such as Florence and Siena with fewer visitors. The countryside changes too as the season progresses. There is something wonderfully atmospheric about mist rising over the hills of the Val d’Orcia, as autumn sunlight begins to warm the stone farmhouses and ochre woodland.

Autumn in Tuscany also brings even more reason to celebrate the region’s food and wine. You can head into the Chianti woods in search of truffles, followed by a generous truffle-themed lunch. We can also arrange a seasonal cookery class at your villa, with dishes making use of the truffles and wild mushrooms that are plentiful at this time of year. Harvest season brings its own sense of excitement to Chianti’s vineyards. Private tours and tastings can be arranged, and you might even choose a luxury villa attached to a winery. This will give you a fascinating insight into all the vendemmia action.

As winter approaches, there are still many reasons to keep visiting Tuscany. You could settle into a peaceful rural villa with a roaring fire and private chef, taking day trips to Florence’s galleries or the medieval towers of San Gimignano. A Tuscan villa stay can also pair beautifully with a few days of Christmas shopping in Rome or Milan. Whatever the season, Tuscany always manages to transport you to beautiful different world.

Ainoa –July 2026

WHERE & WHEN

Where should I stay in Tuscany?

The appeal of Tuscany is vast and multifaceted, and there is a reason that people return to the region again as there are so many different experiences to be enjoyed here. Some of the best places to rent a villa in Tuscany are Chianti and the Val d'Orcia. In both of these regions you can fully immerse yourself in the timeless Tuscan countryside, and truly feel part of the fabric of the land by staying in a converted Tuscan farmhouse. You will also be right in the beating heart of Tuscany’s world-class wine scene, as well as within easy reach of some breathtakingly beautiful medieval towns such as San Gimignano, Pienza, and Montalcino.

For something a little different, you may wish to consider a villa in northern Tuscany, near the glorious walled city of Lucca. Fully-serviced Tuscan villas here are often created from grand palazzi, and are well located for explorations of Pisa and Florence. Alternatively, discover the coastal side of Tuscany with a villa rental in Maremma. Maremma offers pristine beaches, natural reserves, and a distinctive character all of its own.

What is the best time of year to rent a villa in Tuscany?

We consider Tuscany to be a year-round destination, as it has a wealth of attractions that can be enjoyed even during the winter months. In terms of gaining the best all-round experience – including plenty of time outdoors – we particularly recommend visiting Tuscany in either spring or autumn. These periods offer a quieter experience, attractive rental prices, and more of a gentle heat than the peak season of July and August.

Tuscany comes alive with natural beauty from spring to early summer (April to June) and this is a great time to be exploring the countryside and historic towns in pleasant temperatures. The autumn season (September to November) still brings plenty of warm sunshine, as well as autumn colours and excitement of the wine and olive harvest.

ITALIAN VILLAS FOR WINE LOVERS

If savouring the region's best vintages is an important reason for your visit here, read our guide below to discover some of the best Italian villas for wine lovers.

"Producing more wine than any other country in the world and boasting over 2,000 varieties of grape, Italy is a true wine lovers haven. And, while Italian wines are enjoyed the world over, there is nothing like appreciating a fine Chianti Classico or Super Tuscan in situ, admiring bucolic views of rippling gold and sage-green hills, the horizon scattered with clusters of cypress trees and honey-coloured hilltop towns in the distance."

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Fond memories of family holidays in Tuscany made Red Savannah’s local concierge Stefania first fall in love with this exquisite region. Spending more and more time away from her native Rome, Tuscany transformed from being Stefania’s adopted second home to eventually becoming her permanent residence, and she has never looked back. “I fell in love with Tuscany’s history, gastronomy, its wines (for which I myself have a great passion), the quality of life here, as well as the beautiful Tuscan landscapes.”

As well as being a friendly and ever-attentive concierge for guests visiting some of our favourite Tuscan villas, Stefania also employs her love of Tuscany and her unrivalled connections in the region to help Red Savannah source the most authentic local experiences for visitors. No request is too much trouble for Stefania! “After twenty years of experience, my goal continues to be sourcing truly genuine encounters, and to offer exclusive and authentic experiences. This is because my aim is that those who leave Italy take with them beautiful memories, and truly get to know the real Tuscany”.