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.

26 Properties found

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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 hosts B&B accommodation in a stunning location, surrounded by the marvelous vineyards of Chianti. It offers spacious and romantic rooms with all comforts, a restaurant specialized in organic meals, 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 € 530 to € 1220

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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Borgo della MelianaAdd to
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  • Apartments: 22
  • Sleeps: 100
  • Location: Gambassi Terme (Countryside)
  • Daily price: From € 86
  • Weekly price: From € 590

The Tuscany hamlet Borgo della Meliana holiday accommodations for the perfect holiday setting for families, friends & destination wedding or events. Elegant decor, green gardens, panoramic pool & so much more

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Villa PiaggiaAdd to
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  • Rooms: 9
  • Sleeps: 20
  • Location: Montaione (Countryside)

Villa Piaggia, located in Montaione near San Gimignano, is an exclusive and elegant villa that can host up to 20 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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Dianella Wine ResortAdd to
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  • Rooms: 12
  • Sleeps: 24
  • Location: Vinci (Countryside)

The elegant wine resort near Vinci offers suites in a beautiful Medicean villa, surrounded by gorgeous gardens and vineyards. Enjoy the pool and on-site bistro & restaurant, wine cellar visits and tastings for a great stay in Tuscan wine country.

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Villa VianciAdd to
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  • Rooms: 7
  • Sleeps: 14
  • Location: Poggibonsi (Countryside)

Villa Vianci is a family-run holiday villa rental between the hills of Chianti and the historic city of Siena. The beautiful garden offers a large pool, lots of space throughout the villa for up to 14 guests 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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Villa FillinelleAdd to
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  • Apartments: 1
  • Rooms: 3
  • Sleeps: 12
  • Location: Tavarnelle Val di Pesa (Countryside)
  • Daily price: From € 180 to € 300

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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Fattoria PogniAdd to
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  • Apartments: 8
  • Sleeps: 40
  • Location: Certaldo (Countryside)
  • Daily price: From € 106 to € 533
  • Weekly price: From € 650 to € 3200

The eco-sustainable vacation accommodations of this Wine Resort combine the beauty of the Tuscan landscape near Certaldo with delicious wine, modern luxuries, comfortable holiday apartments & a vacation villa rental for up to 10 persons.

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Villa StolliAdd to
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  • Rooms: 4
  • Sleeps: 10
  • Location: Figline Valdarno (Countryside)
  • Weekly price: From € 1400 to € 3200

Spacious & luminous Villa for 10 persons with a private panoramic pool and luxury decor, is in a prime position between Florence & Chianti. Easy access to Siena, Pisa and relaxing spa services.

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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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Osservatorio di MontignosoAdd to
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  • Apartments: 2
  • Sleeps: 11
  • Location: Gambassi Terme (Countryside)

Surrounded by nature and gorgeous gardens with swimming pool, the villa's two apartments are ideal for a group of up to 11 guests wishing an exclusive stay in Tuscany. The location is very central, ideal for day trips to explore the region.

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Montrogoli Holiday HomeOnline
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  • Rooms: 6
  • Sleeps: 12
  • Location: San Casciano in Val di Pesa (Countryside)
  • Weekly price: From € 670 to € 4000

Combine the exhilarating experience of Tuscan art, food & wine with the breath taking views of Chianti at this beautifully restored holiday villa for up to 12 persons in luminous spacious accommodations.

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Residenza Le GrillaieOnline
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  • Rooms: 3
  • Location: Greve in Chianti (Countryside)
  • Daily price: From € 295 to € 430

Those 2 independent villas, sharing an outdoor pool, are located in Chianti area near Florence, which is less than an hour from the residence. The 2 cozy accommodations, both completely equipped, offer a typical rural touch of Tuscany to their guests.

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Residence Casprini da OmeroOnline
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  • Rooms: 12
  • Location: Greve in Chianti (Countryside)
  • Daily price: From € 38 to € 120

This accommodation near Greve in Chianti is well connected to Florence by public transportation. It offers both rooms and apartments for families and groups, as well as an outdoor pool.

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Hotel Villa La PalaginaOnline
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  • Rooms: 4
  • Location: Figline Valdarno (Countryside)
  • Daily price: From € 107 to € 590

Villa La Palagina is surrounded by green hills and is located between Florence and Arezzo. It offers 2 swimming pools and private parking.

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La Canonica Di CortineOnline
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  • Rooms: 18
  • Location: Barberino Val d'Elsa (Countryside)
  • Daily price: From € 104 to € 500

This luxury castle offers bed and breakfast accommodations or apartments. It's located in the Chianti region near Florence and can be the perfect location for special events.

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Fattoria QuercetoOnline
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  • Apartments: 6
  • Rooms: 6
  • Location: Tavarnelle Val di Pesa (Countryside)
  • Daily price: From € 150 to € 166

Set in an ancient building near Tavarnelle Val di Pesa, just half an hour driving from Florence, this farmhouse offers large apartments, as well as outdoor pool, tennis court and bowling lane.

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Hotel Villa CesiOnline
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  • Rooms: 28
  • Location: Impruneta (City,Countryside)
  • Daily price: From € 49 to € 190

This villa is located in Impruneta near Florence within the Chianti. It offers comfortable rooms, as well as a good restaurant and outdoor jacuzzi.

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Country Relais Villa L'OlmoOnline
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  • Rooms: 22
  • Location: Impruneta (Countryside)
  • Daily price: From € 125 to € 6565

Set in a 16th century villa just 10 km from Florence, guests can enjoy a relaxing stay in independent apartments while enjoying the estate's restaurant, swimming pool and surrounding Tuscan countryside. Staff can help arrange tours or book museums.

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Villa Il FedinoOnline
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  • Rooms: 9
  • Location: San Casciano in Val di Pesa (Countryside)
  • Daily price: From € 96 to € 240

Set in 13th century villa in San Casciano Val di Pesa in Chianti. Florence is 30 minutes driving. The hotel has outdoor pool, restaurant and parking. Rooms are elegantly furnished and have modern amenities.

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Villa Casagrande Resort e SPAOnline
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  • Rooms: 60
  • Location: Figline Valdarno (City,Countryside)
  • Daily price: From € 89 to € 160

Set in 14th century noble Villa, this 3 star hotel offers a pleasant stay in the countryside near Florence. It has elegantly furnished rooms, outdoor pool and wellness center.

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Villa San FilippoOnline
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  • Rooms: 32
  • Location: Barberino Val d'Elsa (Countryside)
  • Daily price: From € 120 to € 370

Situated near Barberino Val D'Elsa this hotel is surrounded by green hills, vineyards and olive groves. It offers nice and comfortable apartments.

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Hotel Villa San GiorgioOnline
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  • Rooms: 17
  • Location: Poggibonsi (City,Countryside)
  • Daily price: From € 61 to € 110

Recently refurbished, this nice villa is located in Chianti. It offers nice and comfortable rooms and outdoor pool.

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Badia a ColtibuonoOnline
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  • Rooms: 13
  • Location: Gaiole in Chianti (Countryside)
  • Daily price: From € 139 to € 250

This wine resort in Chianti is located in beautiful Gaiole in Tuscany. It is set in ancient and carefully restored abbey equipped with modern comforts.

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Villa La MediceaOnline
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  • Sleeps: 12
  • Location: Impruneta (Countryside)

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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