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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. The view from this accommodation was stunning! Looked right out over the whole of Tuscany. We spent many evenings sitting out with one of their wines watching the sunset. Very comfortable beds and traditional Tuscan style. Just beautiful. Lovely surprise having our beds made everyday. This place was one of our highlights from our whole trip!

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9.3
Superb
1,014 reviews
Price from
US$150
per night

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. Great team, friendly and spot on with help and advice! Just amazing breakfast and convenient location!!

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9.3
Superb
1,208 reviews
Price from
US$119
per night

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. Amazing location, everything was picture perfect. Check in/out was smooth, big area to relax. The staff was helpful and gave recommendations. Prior to arrival communication was fast and helpful. I also recommend vinery tour and wine sampling provided by the host.

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9.4
Superb
1,245 reviews
Price from
US$80
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. Everything is great, ,Alessandra and her family are amazing, they make sure that you have everything that you need. The nature and the location is also great.

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9.8
Exceptional
105 reviews
Price from
US$151
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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9.4
Superb
120 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
145 reviews
Price from
US$66
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
162 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. Amazing service, they made us feel so welcome. We arrived really late, so all restaurants in the area was about to close. In 15 minutes they made us the most amazing dinner. The pool area was a dream, and the peace and quiet was amazing. The only thing you could hear if you sat outside in the evenings were crickets. The wine from the winery was also really good. We really hope to be going back some day.

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9.6
Exceptional
154 reviews
Price from
US$261
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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9.4
Superb
107 reviews
Price from
US$80
per night

Situated 28 km from Ponte Vecchio, 28 km from Uffizi Gallery and 28 km from Piazzale Michelangelo, Bonaventura features accommodation located in Greve in Chianti. The property is around 30 km from Piazza della Signoria, 30 km from Cathedral of Santa Maria del Fiore and 30 km from Piazza del Duomo di Firenze. Free WiFi is available throughout the property and Piazza Matteotti is 1.5 km away. It was a beautiful area. The property was conveniently located in a nice little town and it was overlooking the beautiful view of the vineyard. We enjoyed our stay and would recommend this location if you want a nice relaxing vacation!

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9
Superb
122 reviews
Price from
US$134
per night

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