Siena and Chianti

Your dream destination awaits in Siena. We have a superb collection of hand-picked villas in this region of Tuscany to suit all your needs.

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Casetta Busecchio | Private Villa With Pool Ideally Located in Tuscany, Italy

Casetta Busecchio is a tranquil holiday retreat, perfect for those planning their Tuscany holiday and seeking a peaceful retreat in the Tuscan countryside. This renovated farm cottage offers breathtaking views of Chianti and the chance to spot local wildlife. With its private pool, stone terrace, and easy access to Florence, Siena, and charming local towns, this villa is an ideal base for a villa holiday in Tuscany, Italy.

Charming Hamlet in Tuscany, Italy | Perfect for Your Next Getaway to the Italian Countryside

Montebuoni is a charming hamlet of 15 restored villas set in the Tuscan countryside. Once a wine and olive oil estate, the hamlet offers a peaceful retreat with a shared pool, children's pool, and tennis court. Located near Lecchi in Chianti, it's perfect for exploring Siena, Florence, and San Gimignano. Learn more on our site. -- tuscany | tuscany villa | tuscany italy | tuscan countryside | italian aesthetic | siena | florence | summer vacation | italian holiday inspo

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Villas near Montepulciano | To Tuscany

Our exclusive collection of villas near Montepulciano offers a perfect blend of luxury and authentic Tuscan charm. Surrounded by rolling vineyards and picturesque countryside, each villa provides swimming pools, and modern amenities for a relaxing stay. Ideal for family holidays or romantic getaways.

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Villa in Tuscany, Italy with Five Bedrooms | 10-13 Guests

Stay at Villa Il Molinaccio, a beautifully restored 10th-century watchtower now offering modern comforts amidst serene, private grounds. Enjoy a secluded pool, outdoor dining under a gazebo, and a range of amenities, all set in the peaceful Tuscan countryside.

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Casa Cerralta | Tuscan Villa in Val D'Orcia, Italy

Casa Cerralta offers luxurious accommodation for up to 14 guests, with stunning views of Brunello vineyards and Val D’Orcia’s rolling hills. This spacious villa features traditional Tuscan charm, a private pool, and multiple outdoor dining areas, perfect for large families or groups of friends. - montepulciano italy | montepulciano | italy travel | montepulciano tuscany | montepulciano wine | tuscany aesthetic | italy travel guide | tuscany italy | italy aesthetic | montepulciano italy photo

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Tuscan Villa in the Heart of Chianti Classico - Poggio Tondo - To Tuscany

Stay in the heart of Chianti Classico at Poggio Tondo, with sweeping views of the Tuscan countryside. The villa offers spacious terraces, perfect for enjoying a glass of local wine while watching the sun go down. Spend the day by the pool, soaking up the Tuscan sun surrounded by olive groves, or explore iconic Tuscan destinations like Siena and Florence nearby. The perfect summer vacation starts here!

Solaria di Santa Maddalena | Tuscan Villa Ideal for Large Groups or Families | Great Location

Solaria di Santa Maddalena offers a luxurious retreat surrounded by stunning Tuscan vineyards and olive groves. The villa boasts seven bedrooms, a private pool, and multiple outdoor areas perfect for al fresco dining with breathtaking views. Located near Vagliagli, Siena, and Florence, it’s an ideal base for exploring Tuscany’s historic sites and renowned wineries.

Tuscan villa located in Chianti Classico | Rosa di Chianti

Rosa di Chianti is a charming Tuscan cottage located between Castellina and Radda. The villa features a spacious terrace with a private pool, perfect for relaxation and al fresco dining, looking out over stunning countryside views. Centrally situated in the Chianti Classico wine region, it's an ideal base for exploring Siena, San Gimignano, and Florence. - tuscan villa | tuscany | tuscany italy | siena | chianti | chianti tuscany | florence

Tuscan villa close to Siena | Perfect for relaxation and exploration | Tuscany, Italy

Podere Gabbiano, ideally located between Castellina in Chianti and Panzano in Chianti, offers a unique blend of history, luxury, and breathtaking beauty. Guests can enjoy stunning sunsets over 360-degree views of vineyards and olive groves. Enjoy pizza evenings at the villa with the villas original stone oven. -- tuscany | tuscany italy| tuscan villa | villa | tuscan views | chianti | chianti tuscany | castellina in chainti | summer vacation | european destination

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Modern villa in San Gimignano, Tuscany, Italy | Ideal location | Private pool

Discover Vallebuia, an exquisite retreat in the heart of Tuscany. Located near San Gimignano, Siena, and Florence, this historic villa offers breathtaking views of olive groves and vineyards. Enjoy spacious interiors with contemporary furnishings, a stunning pool, and lush gardens, making it ideal for groups of friends and family. – san gimignano | san gimignano italy | san gimignano tuscany | tuscany aesthetic | summer vacation | tuscany villa | tuscany villa italy | tuscany aesthetic

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Restored farmhouse in the Tuscan hills | Private retreat with private pool | Great location

Experience ultimate comfort at Villa Vetrichina, a beautifully restored farmhouse on the edge of Tuscany and close to Umbria. Perfect for groups, offering easy access to Val D’Orcia, Monte Amiata, and world-famous cities like Orvieto and Perugia. Enjoy the spacious dining room, cosy terrace, private forest, and unique local craftsmanship, bringing the villa’s traditional features to life. Find your home away from home at Villa Vetrichina.

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Villa in the Chianti ideally located for exploring the local area | Private pool

Discover Casanovina, an exquisite retreat with a secluded pool and breathtaking views of the Tuscan landscape. Just 2km from the charming town of Castellina in Chianti, this villa offers easy access to Siena, San Gimignano, and Florence. With space for up to eight guests, it’s the perfect blend of luxury and convenience for your Tuscan getaway.

A small hamlet in the heart of the Chianti | Ideal location for exploring | Castellina in Chianti

Discover the essence of Tuscan countryside living at Podere di Casalta, between Castellina and Panzano in Chianti. Relax by the sun-soaked pool while enjoying panoramic views of oak forests, vineyards, and hilltop towns. Whilst you watch the sunset, why not plan a day trip to Siena, Florence or one of the many Chianti villages nearby, savouring organic Chianti wine or dining on local delicacies, immersing yourself in the true heart of Chianti living?

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Villa for two couples in the Chianti | Ideal location - few kilometers from Castellina in Chianti

Escape to Antica Posta, nestled in the heart of Chianti, just moments away from Castellina in Chianti and Radda in Chianti. The villa, formed from two former stone farm buildings, creates a studio and one-bed apartment, ensuring guests can enjoy privacy. With private terraces, a garden oasis, and a shared pool, it's the perfect retreat for couples amidst panoramic views of the Tuscan hills. Enquire today with one of our villa specialists.

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Two-bed villa in the Chianti | Great location | Private pool and countryside views

Experience quintessential Tuscan charm at Macia Viva, near Castellina in Chianti, with breathtaking views of vine-clad hillsides and valleys. This two-bedroom villa boasts stylish furnishings, offering the perfect retreat for couples, friends, or small families. With its private pool and proximity to charming towns like Castellina in Chianti, Siena, and Florence, every moment at Macia Viva promises relaxation and exploration in equal measure. Learn more on our website.