A holiday home with a private pool in the Chianti is an ideal choice for those wishing to experience Tuscany in its most authentic and timeless form. Surrounded by gently rolling hills, olive groves and world-renowned vineyards, the Chianti region offers a rare combination of natural beauty, cultural heritage and exceptional cuisine.

From your villa with private pool, you can enjoy sweeping views over vineyards and countryside while exploring the historic villages of Greve, Castellina, Radda and Gaiole in Chianti. These towns are known for their small piazzas, excellent wineries and traditional trattorias, where a glass of Chianti Classico is part of everyday life.

Our handpicked Chianti villas with private pool offer comfort, privacy and a sense of place. Many of the properties are carefully restored country houses or historic villas that preserve the character of the Tuscan landscape while providing modern amenities for a relaxed stay.

Whether you are planning a culinary journey with wine tastings, a peaceful retreat in nature or cultural excursions to Florence, Siena or San Gimignano, a holiday home in the Chianti provides an ideal base for discovering the heart of Tuscany.

Immerse yourself in the Tuscan way of life and enjoy a luxury villa with private pool in the hills of the Chianti.

The Chianti region is one of the most beautiful areas of Tuscany and is world-famous for its rolling hills, vineyards and charming villages. A holiday here is defined not only by excellent wine, but also by an exceptional landscape and a deeply rooted Tuscan way of life. A holiday home in Chianti with private pool offers the ideal way to experience this special region in complete privacy.

Luxury Chianti Villas – Elegance and Comfort among Vineyards

If you are looking for an exclusive retreat, a luxury villa in Chianti is an excellent choice. These villas combine traditional Tuscan character with modern comfort and usually feature generous gardens, panoramic views and private swimming pools. Surrounded by vineyards and olive groves, they offer peace, space and a refined setting for a relaxed stay in the countryside.

Exclusive Holiday Homes in the Chianti Region with Pool

Whether in Greve, Castellina, Radda or Gaiole in Chianti, an exclusive holiday home with private pool provides a secluded escape immersed in nature. Many of these villas are carefully restored country houses that preserve original features such as wooden beams and terracotta floors, while offering modern amenities for a comfortable holiday.

Chianti Villas with Pool and Vineyard Views – Enjoy Panoramic Landscapes

A holiday home in Chianti with pool and vineyard views allows you to fully appreciate the Tuscan landscape. Start the day with breakfast on the terrace overlooking green hills and vineyards, and end the evening with a glass of Chianti Classico under a star-filled sky.

Villas in Chianti with Pool Close to Wineries

Chianti is a destination for food and wine lovers, home to renowned wineries and traditional trattorias serving local specialities. A holiday home in Chianti with pool close to wineries is ideal for guests wishing to take part in wine tastings, cellar visits and culinary experiences directly in the region.

Holiday Homes in the Most Beautiful Villages of Chianti

Holiday Home in Greve in Chianti – A Central Starting Point

Greve in Chianti is considered the gateway to the region and one of its main meeting points. The town is known for its spacious central square, traditional wine shops and a high concentration of well-known wineries nearby. A holiday home in or near Greve is particularly suitable for guests who enjoy short distances to restaurants, markets and wine tastings while actively exploring Chianti.

Holiday Home in Castellina in Chianti – Historic Charm and Nature

Castellina in Chianti is set on a hill between Florence and Siena and combines medieval architecture with a particularly scenic landscape. The well-preserved old town, with its walls, small shops and cafés, invites leisurely strolls. Holiday homes around Castellina are often located in quiet surroundings among vineyards and olive groves, offering a balanced mix of cultural exploration and relaxation in nature.

Holiday Home in Radda in Chianti – Authentic Nature and Tuscan Atmosphere

Radda in Chianti is one of the most authentic villages in the region, located on a hilltop in the heart of the classic Chianti area. Small and unspoilt, it is surrounded by vineyards and woodland. A holiday home near Radda is ideal for guests seeking tranquillity, open views and direct access to walking or cycling routes, away from the main tourist routes.

Holiday Home in Gaiole in Chianti – Wine and Cultural Heritage

Gaiole in Chianti lies east of the classic Chianti villages and is characterised by a wide, open landscape dotted with historic castles and renowned wineries. The area is especially popular with wine lovers and culturally minded travellers. Holiday homes around Gaiole are often set in very peaceful locations, offering privacy and an excellent base for visiting castles, wineries and the surrounding valleys.

Family-Friendly Holiday Homes in Chianti

Family-Friendly Holiday Home in Chianti with Fenced Pool

For families travelling with children, safety is an important consideration. A family-friendly holiday home in Chianti with a fenced pool allows parents to relax and enjoy outdoor life while ensuring a secure environment for younger guests.

Rustic Chianti Farmhouses with Pool and Authentic Tuscan Character

Those wishing to experience traditional rural Tuscany may prefer a rustic holiday home in Chianti with private pool. These properties are often beautifully restored farmhouses that retain their original Tuscan character and atmosphere.

Your Perfect Chianti Holiday – Book Your Villa with Pool

A holiday home in Chianti offers a unique blend of relaxation, nature, culture and gastronomy. Whether you are looking for a romantic retreat, a spacious villa for friends or a family-friendly holiday home with pool, Chianti provides the ideal setting for an unforgettable stay.

Experience the spirit of Chianti and book your holiday home with private pool among the vineyards of Tuscany.

Chianti – Where the Soul of Tuscany Lives

There are places that represent more than a landscape – they embody an entire way of life. Chianti is one of those places. A region of gentle hills, golden fields and endless vineyards that quietly settles into the heart of every traveller. Driving along its winding roads, past centuries-old farmhouses and avenues of cypress trees, one immediately senses that this is where the soul of Tuscany truly resides.

Wine Villages Shaped by History and Character

The villages of Chianti are not conventional destinations; they are living time capsules, each carrying layers of history. Greve in Chianti, often described as the gateway to the region, welcomes visitors with its elegant arcaded piazza. Every Saturday morning, the square comes alive with markets offering fresh pecorino, air-dried salami and, of course, Chianti wine. At the centre stands a statue of Giovanni da Verrazzano, the explorer who first charted New York Bay – a reminder that Chianti has long been a land of travellers, curiosity and outward-looking spirit.

Further south lies Castellina in Chianti, enclosed by ancient defensive walls. The underground passage known as the Via delle Volte, once part of the fortifications and now home to small boutiques and wine shops, makes wandering through the village a quietly captivating experience. From above, the view opens onto rolling hills and vineyards – Tuscany as it exists in the imagination.

Perched on one of the highest points in the region is Radda in Chianti, once the capital of the medieval Lega del Chianti, a powerful wine alliance. Even today, Radda feels like a living postcard. Narrow streets lead to small squares lined with family-run businesses and traditional trattorias. Sitting beneath shaded pergolas with a glass of Chianti Classico Riserva, one quickly notices how time seems to slow.

Gaiole in Chianti, known for its imposing castles and historic estates, is another highlight for wine and history enthusiasts. The Castello di Brolio, owned by the Ricasoli family for more than a thousand years, is widely regarded as the birthplace of modern Chianti wine. Visitors can explore ancient cellars, taste refined wines and listen to stories that reach far back into Tuscany’s past.

A Culinary Journey through Chianti

In Chianti, food is not simply eaten – it is enjoyed. The cuisine reflects the landscape itself: honest, rooted and unpretentious. Perhaps the most iconic dish is the Bistecca alla Fiorentina, a thick-cut T-bone steak from Chianina cattle, grilled to perfection and seasoned with little more than salt, olive oil and rosemary. It is Tuscan tradition in its purest form.

Fresh pasta plays an equally central role. Pici, thick hand-rolled noodles, are often served with rich wild boar ragù, while ribollita – a hearty soup of vegetables, white beans, bread and black cabbage – remains one of the region’s most comforting classics.

No Tuscan meal would be complete without olive oil. The olive groves of Chianti produce some of Italy’s finest extra virgin oils – golden-green in colour, intense in flavour and essential to the local kitchen.

Wine – The Heart of Chianti

No product is more closely associated with Chianti than its wine. Chianti Classico, marked by the iconic black rooster on the label, is synonymous with winemaking excellence. Based primarily on the Sangiovese grape, it reveals characteristic notes of cherry, leather and Mediterranean herbs.

Many of the region’s finest wineries welcome visitors, offering insight into the art of winemaking. Whether through guided cellar tours, tastings among the vines or conversations with passionate winemakers, these experiences are an integral part of any journey through Chianti.

Alongside Chianti Classico, the region is also home to outstanding Super Tuscans – powerful, elegant wines born in the 1970s, when pioneering producers began blending Sangiovese with international varieties such as Merlot and Cabernet Sauvignon.

Chianti – A Way of Life

Anyone who has travelled through Chianti knows that this region is far more than a holiday destination. It is a way of life. Whether standing on a remote hilltop estate, sitting in a small trattoria filled with locals, or enjoying a glass of wine as the sun sinks behind the vineyards, Chianti possesses a quiet magic that is not only seen, but deeply felt.