The Chianti region is full of beautiful historical villas. These lodgings are exclusive accommodations of great charm; perfect if you wish to experience the luxury and elegance typical of Florentine noble families, that used to have their own villa in the countryside. Chianti villas have been carefully restored to their former splendour and offer refined and charming accommodations fully equipped with all modern comforts and facilities.

35 Properties found

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Villa PiaggiaAdd to
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  • Rooms: 9
  • Sleeps: 17
  • Location: Montaione (Countryside)

Villa Piaggia, located in Montaione near San Gimignano, is an exclusive and elegant villa that can host up to 17 guests. The villa and its swimming pool is surrounded by a large park and vineyards, enjoying a beautiful view over the Tuscan countryside.

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Villa DianellaAdd to
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  • Rooms: 4
  • Sleeps: 8
  • Location: Vinci (Countryside)

Small elegant bed and breakfast near Vinci in a beautiful Medicean villa. The gardens are the perfect setting for weddings and special meetings, with views over the surrounding vineyards and olive groves.

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Il CelleseAdd to
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  • Apartments: 7
  • Sleeps: 25
  • Location: Castellina in Chianti (Countryside)
  • Weekly price: From € 400 to € 2100

Located in Castellina in Chianti, in the heart of Chianti area, this typical Tuscan farmhouse offers 7 independent apartments and a gorgeous villa, a large salt water pool with view on the surrounding hills and restaurant.

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Villa il PoggialeAdd to
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  • Apartments: 1
  • Rooms: 24
  • Sleeps: 48
  • Location: San Casciano in Val di Pesa (Countryside)
  • Daily price: From € 80 to € 400

This villa B&B is situated in a stunning location, surrounded by the marvellous nature of Chianti. It offers cozy, spacious and romantic rooms provided with all modern comforts, a Tuscan restaurant with organic products, a spa and swimming pool.

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Villa Le TorriAdd to
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  • Apartments: 9
  • Sleeps: 26
  • Location: Montespertoli (Countryside)
  • Weekly price: From € 485 to € 1005

Stone villa from the 13th century offers apartments for your vacation in the Chianti hills near Florence. Managed directly by the owners, guests receive personal attention and service while enjoying the self-catering accommodation and the villa's pool.

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Villa VianciAdd to
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  • Rooms: 6
  • Sleeps: 12
  • Location: Poggibonsi (Countryside)

Villa Vianci is a family run luxury rental between the hills of Chianti and the historic city of Siena. There is a beautiful green garden with pool, lots of family space throughout the villa for up to 12 PAX on holiday in Tuscany

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Villa di CabbiavoliAdd to
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  • Sleeps: 12
  • Location: Castelfiorentino (Countryside)

An ancient castle sitting on the gentle hills of Chianti, finely restored and turned into a beautiful luxury villa perfect for 12 people. It offers a private, gorgeous outdoor pool and exclusive services to make your stay unforgettable.

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Torre a ConaAdd to
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  • Apartments: 9
  • Rooms: 4
  • Sleeps: 42
  • Location: Rignano sull'Arno (Countryside)
  • Daily price: From € 120 to € 530
  • Weekly price: From € 600 to € 4700

Charming farmhouse with pool situated in the Chianti area near Florence. It offers rooms and independent apartments, all recently restored and finely decorated and a huge, wide park surrounded by hectars of olive trees and vineyards.

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Tenuta MorianoAdd to
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  • Apartments: 20
  • Rooms: 20
  • Sleeps: 58
  • Location: Montespertoli (Countryside)
  • Daily price: From € 80
  • Weekly price: From € 480 to € 1435

Immersed in the green hills of Chianti, in a typical Tuscan landscape, this beautiful farmhouse offers spacious apartments equipped with all amenities. Guests can enjoy a beautiful pool, tennis court and guided tasting of the farm's excellent wines.

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Borgo ArgeninaAdd to
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  • Sleeps: 22
  • Location: Gaiole in Chianti (Countryside)
  • Daily price: From € 160 to € 420

A romantic & enchanting way to discover the mysteries of Tuscany at Borgo Argenina, where the B&B and private villas combine the savour perfumes from the kitchen, and the warm hospitality of your hostess for a memorable holiday adventure.

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Podere Villa BassaAdd to
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  • Apartments: 2
  • Sleeps: 18
  • Location: Montespertoli (Countryside)
  • Weekly price: From € 1190 to € 2270

The two extra large vacation rental apartments at Podere Villabassa near Montespertoli, feature fantastic gardens, terraces, pool & hot tub. The holiday accommodations can be combined into one large villa with communicating doors for groups of 18 PAX

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Il CorbezzoloAdd to
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  • Sleeps: 4
  • Location: Gambassi Terme (Countryside)
  • Weekly price: From € 750 to € 980

A one bedroom private villa rental for vacation near San Gimignano and Chianti, promises tranquility, comfort & romantic Tuscan landscapes for your holiday. Perfect base also for a honeymoon.

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Podere PatrignoneAdd to
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  • Apartments: 6
  • Rooms: 15
  • Sleeps: 32
  • Location: Castellina in Chianti (Countryside)
  • Daily price: From € 115

The ambiance at this farmhouse brings together family & friends, nature & relax. The villa rental & self catering apartments provide an ideal base for exploring Tuscany in its natural state: hiking, swimming, dinner banquets & small town adventures.

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Villa FillinelleAdd to
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  • Apartments: 1
  • Rooms: 3
  • Sleeps: 12
  • Location: Tavarnelle Val di Pesa (Countryside)
  • Daily price: From € 180 to € 280

Lush gardens, charming decors & panoramic views. This prestigious medieval Villa has been totally restored for your holiday near Chianti & Florence. It offers two perfect solutions: 4 charming B&B rooms or the entire villa for a deluxe holiday.

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Villa La MediceaAdd to
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  • Sleeps: 12
  • Location: Impruneta (Countryside)
  • Weekly price: From € 3400 to € 3800

Historical villa on the edge of Chianti is just 7 km from the center of Florence. The rental villa includes spacious accommodations, modern amenities as well as a beautiful pool with panoramic views over the countryside.

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Your Summer Residence

Many villas in Chianti are historical homes, dating back to the Renaissance, when wealthy Florentine and Sienese families used to move to their summer residences to escape the heat of the city.

After a careful restoration, they have been beautifully converted in many different types of accommodations: hotels, bed and breakfast, and fully equipped apartments.

They also offer a number of amenities and services, such as swimming pool, spa, good restaurants, guided tours and excursions, horse back riding, wine tastings, and much more. Chianti villas are also a great location for weddings and special events in Tuscany.


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