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The best holiday rentals in Chianti

Check out our pick of great holiday rentals in Chianti

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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Offering an outdoor pool and a restaurant, Fattoria di Cinciano is located in Poggibonsi, a 10-minute drive from the centre. Free WiFi access is available in all areas.

Each apartment will provide you with a satellite flat-screen TV, air conditioning and a kitchenette with a microwave. Featuring a shower, the private bathroom also comes with a hairdryer and towels. everything was perfect, the place is huge, so old and full of history (well maintained building, very clean and nice)

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9.3
Superb
1,011 reviews

Set in the Chianti hills, this stone guesthouse features an outdoor pool and is located in the rural hamlet of Salvadonica. Surrounded by vineyards and olive groves, it offers en suite accommodation with Tuscan-style furnishings and free Wi-Fi. Stunning location, wonderful staff, modern comfortable rooms in a stunning Tuscan farm setting

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9.3
Superb
1,161 reviews

Set within 24 km of Piazza del Campo and 29 km of Piazza Matteotti, Agriturismo San Sano offers rooms with air conditioning and a private bathroom in Gaiole in Chianti. This farm stay has a pool with a view, a garden and free private parking. The farm stay features family rooms. This is an excellent guest house. The owners are wonderful. The room is wonderful. And the wine tasting is perfect. I hate Chianti. I love Chianti Classico. You can figure that out when you get there. The drive to the hotel is a bit of fun if you like hill driving and the village is unreal. You cannot miss in San Sano. We will be back with friends. You should, too.

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9.3
Superb
1,260 reviews

CastelBigozzi is surrounded by the Tuscan countryside, 12 km from San Gimignano. It offers an outdoor swimming pool with hydromassage, and rustic, air-conditioned rooms. You can book free guided excursions on the Via Francigena path. It was exactly what was promised. An old building in the heart of Tuscany int the middle of an olive orchard. Unfortunately we only spent a night there and wished we could have stayed longer. The restaurant was also very nice with a nice view of the sunset over the hills. The rooms are extremely spacious, clean and beautiful. Overall, we would come back at anytime in a heartbeat

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9
Superb
1,062 reviews
Price from
US$116
per night

Situated within 25 km of Piazza Matteotti and 36 km of Piazzale Michelangelo, La Pimpinella di Semifonte features rooms with air conditioning and a private bathroom in San Donnino. This property offers access to a terrace and free private parking. The farm stay has family rooms. Hosts were incredible. Food felt like a hug. Our rooms were SO COOOL. We cannot wait to return. It was a hard goodbye.

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9.8
Exceptional
106 reviews
Price from
US$150
per night

Set in Colle Val D'Elsa, Palazzo Galganetti Betti offers accommodation 26 km from Piazza del Campo and 41 km from Piazza Matteotti.

Featuring a private bathroom, units at the holiday home also have free WiFi. I was met by member of the property team and escorted to the residence. Super convenient.

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9.5
Exceptional
123 reviews
Price from
US$160
per night

Offering city views, Mansarda Brunelleschi is an accommodation located in Staggia, 21 km from Piazza del Campo and 33 km from Piazza Matteotti. Both free WiFi and parking on-site are available at the apartment free of charge. The accommodation provides private check-in and check-out and a minimarket for guests. Nice apartment with artistic touch to it

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9
Superb
150 reviews
Price from
US$71
per night

Situated within 27 km of Piazza Matteotti and 28 km of Piazza del Campo, La Corte del Chianti Classico features rooms with air conditioning and a private bathroom in Gaiole in Chianti. Private parking is available on site at this recently renovated property. The property offers a pool with a view, a garden and rooms with garden views. The Owners really put a lot of time and effort into making this place special. Peaceful getaway. Very newly updated, very clean and well designed. Thoughtful touches like an above average breakfast. Very friendly owners. Willing to make sure your stay meets your needs. Will come back. Close to a couple great wineries.

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9.7
Exceptional
165 reviews

20 km from Piazza del Campo, BORGO A MONTI di Sotto is a recently renovated property located in Gaiole in Chianti and provides air-conditioned rooms with free WiFi and private parking. With garden views, this accommodation features a patio. The holiday home offers parking on-site, a pool with a view and luggage storage space. The apartment was amazing. Everything was super clean. The pool and also view of the Pool is a dream. The kitchen is equipped with all the basics you need and there was also a welcome package and a bottle of wine. We would always come back!

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9.6
Exceptional
155 reviews
Price from
US$240
per night

Situated in San Casciano in Val di Pesa, 18 km from Pitti Palace and 19 km from Strozzi Palace, il Gallo offers air conditioning. The property is located 19 km from Santa Maria Novella, 19 km from Piazza Matteotti and 21 km from Ponte Vecchio. Free WiFi is available throughout the property and Piazzale Michelangelo is 18 km away. Warm, clean, new and cozy. We would stay again.

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9.5
Exceptional
112 reviews
Price from
US$79
per night

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