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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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 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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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 € 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: 10
  • Rooms: 10
  • Sleeps: 36
  • Location: Montespertoli (Countryside)
  • Daily price: From € 80
  • Weekly price: From € 480 to € 1435

Immersed in the green hills of Chianti, this beautiful farmhouse offers spacious apartments equipped with all amenities. Guests can enjoy a beautiful pool, play area 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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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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La CanigianaAdd to
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  • Apartments: 2
  • Sleeps: 6
  • Location: San Casciano in Val di Pesa (Countryside)
  • Daily price: From € 90 to € 300
  • Weekly price: From € 630 to € 2100

The vacation apartments at Agriturismo La Canigiana are positioned in a panoramic position just outside of Florence. Cozy & comfortable, these self-catering apartments are for up to 3 persons each, share a lovely pool, WiFi & easy access to day trips.

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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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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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La Casa in ChiantiAdd to
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  • Apartments: 2
  • Sleeps: 6
  • Location: Gaiole in Chianti (Countryside)
  • Daily price: From € 180 to € 300

This beautiful farmhouse near Gaiole in Chianti features 2 holiday rental villas for families & friends exploring Tuscany. Great views, a Tuscan atmosphere, attentive service & homey comforts for a tranquil vacation.

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Casa Vacanze SoleadoAdd to
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  • Rooms: 5
  • Sleeps: 10
  • Location: Gambassi Terme (Countryside)
  • Weekly price: From € 1150 to € 3000

This beautifully restored 5 bedroom vacation villa rental features modern comforts, private pool & fabulous panoramic views in the tranquil countryside of Chianti, the area famous for wine & olive oil.

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Agriturismo ColognoleAdd to
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  • Apartments: 6
  • Rooms: 4
  • Sleeps: 53
  • Location: Pontassieve (Countryside)
  • Daily price: From € 48 to € 680
  • Weekly price: From € 290 to € 3400

Marvellous setting for this rural countryhouse in the heart of Chianti, with easy access to Florence. Clean, tiny and lovely accommodation in rooms, apartments or independent villas.

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La CertaldinaAdd to
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  • Apartments: 8
  • Sleeps: 36
  • Location: Certaldo (Countryside)
  • Daily price: From € 55 to € 135

The family & pet-friendly vacation apartments La Certaldina provide the perfect relaxing atmosphere for a holiday in Tuscany. Enjoy the views, the pool, the food & wine while staying close to Certaldo, Florence & Chianti.

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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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Villa Medicea di LillianoAdd to
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  • Apartments: 5
  • Rooms: 5
  • Sleeps: 32
  • Location: Bagno a Ripoli (Countryside)
  • Daily price: From € 175 to € 575

The elegant and luxurious apartments at this wine estate offer comfort in style, as well as stunning panoramic views of Florence and the countryside. Pool for relaxing, wine tastings and great base for exploring Chianti & Tuscany.

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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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