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Villasnear Siena

Our handpicked collection of the best villas near Siena offers the perfect base to experience the beauty and culture of the Chianti countryside. 

A To Tuscany villa near Siena captures the essence of countryside living, offering peaceful retreats surrounded by olive groves and vineyards. Stay in the Chianti hills to explore famous local towns and sample world-class wines or head south to Rapolano Terme and Pienza. 

Our collection features the best villas to rent near Siena for an unforgettable Tuscan stay. Whether you are looking for a family holiday, romantic escape, or touch of luxury, each home offers comfort, privacy, and timeless Tuscan charm.

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FAQs

How far are the villas in Chianti from Siena?

Most of our villas are within an hour's drive of Siena, ideal for those looking to enjoy the tranquillity of the Tuscan countryside and easy access to one of the region's most popular cities. The scenic journey will take you through vineyards and olive groves and past picturesque towns and villages hidden among the hills, offering a true taste of Tuscany along the way.

Is it better to stay in a villa or a hotel in Siena?

Choosing a villa near Siena allows guests to experience Tuscany at their own pace, with the space and privacy to relax in full. Unlike hotels in the city centre, a villa in the surrounding countryside offers more outdoor space to enjoy the sunny Tuscan weather, pools, and panoramic views, whilst keeping Siena within easy access for day trips. This is what makes a villa holiday ideal for families, groups, or couples seeking more from their Tuscan getaway.

Is Siena worth visiting?

Siena is one of Tuscany’s most popular cities, famous for its medieval streets, iconic Piazza del Campo and impressive Duomo di Siena. The city is rich in history, art, and tradition, making it a must-visit destination for those staying in a villa in the surrounding area. 

The city can get very busy and hot during the peak summer months. For a quieter visit with fewer crowds and cooler temperatures, we suggest visiting in the spring or autumn, both equally lovely times of year to see the city and stay in Tuscany.

For more information, read our Siena travel guide.

What towns are near Siena?

Some of Tuscany’s most beautiful towns and villages surround Siena. The Chianti sits north of Siena and is where you will find plenty of Chianti wine towns to explore, such as Castellina, Radda, Gaiole, Lecchi and many more. For those staying further south of the city, the thermal baths of Rapolano Terme, and the Renaissance gems of Montepulciano and Pienza await. All are easily accessible from our villas near Siena, perfect for day trips and exploring local culture, food, and wine. 

Learn more about these towns and villages and those across the region in our Tuscany travel guide.

What is there to do in while staying in a Chianti villa?

There is a lot to do when renting a villa in the Chianti, from wine tastings at renowned Chianti Classico wineries and estates, visiting medieval towns and villages, countryside walks and cycling routes, to day trips to Florence and Siena. Not to mention finding the best restaurant closest to your villa and trying local delicacies. For more relaxing days, guests can relax by the pool, enjoy meals on the terrace and soak up the surrounding views.

Why is the Chianti in Tuscany famous?

Chianti is world-famous for its wine production, particularly Chianti Classico, as well as its iconic rolling hills and medieval villages. Unsurprisingly, it is one of the most popular areas of Tuscany with visitors, combining natural beauty, gastronomy, and history.

SUPERB VILLAS

Our carefully chosen villas are set in some of Tuscany’s most desirable locations, each with unique character, comfort, and extraordinary views.

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