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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
1,006 reviews
Price from
US$246
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
1,212 reviews
Price from
US$226
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. PERFECT !! it was just an amazing experience the resort is so beautiful and well-kept, great location with stunning views the staff was lovely and helpful, provided great service and recommendations

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9.3
Superb
1,248 reviews
Price from
US$93
per night

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. Very nice place and location in Tuscany.i suggest it 100%.

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9
Superb
1,087 reviews
Price from
US$177
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
113 reviews
Price from
US$162
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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9.1
Superb
139 reviews
Price from
US$70
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 warmth of the hosts, the peace of the surroundings and the gorgeous pool

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9.6
Exceptional
146 reviews
Price from
US$183
per night

Set within 13 km of Ponte Vecchio and 13 km of Uffizi Gallery, B&B Casa Decimo offers rooms with air conditioning and a private bathroom in Greve in Chianti. This bed and breakfast provides free private parking and luggage storage space. The accommodation features a housekeeping service and bicycle parking for guests. We liked this structure and felt at home because of our host, Giuseppe and Mariko-san. The structure is a villa-style B&B with an east-facing garden where you can enjoy breakfast or simply relax and take in the fresh air. Our room is pretty clean and cozy with everything well maintained and working perfectly, which made us feel at ease especially after a tiring day in the city. The location of the hotel is close to the city center which is about a 30 min bus ride. We mainly visited Florence based on the map with routes that ​​Giuseppe recommended. If you have a car, you can also explore more brilliant views in Sienna, Pizza, etc. Giuseppe and Mariko-san served us a full Italian-style breakfast with a genuine warmth everyday. We enjoyed it in the garden while appreciating the Tuscan landscape and sunshine, or in the tidy and fully equipped kitchen when it rained. They offered us a great amount of help, even though they didn’t have to. We arrived late the first day getting there without carrying any food. We were moved when Giuseppe kindly offered to not only translate the menu but also order the pizzas for us. Mariko-san looked up the bus timetable so that we could be well prepared the next day to Florence. What’s more, Giuseppe also set up tables with everything we needed and helped us warm up the food. Thanks to their hospitality, we had a wonderful time there. We would love to come back sometime and recommend it to our friends. Maybe next time we’ll have the chance to see Naomi in person :)

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9.7
Exceptional
113 reviews
Price from
US$143
per night

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. Property is nice and quite and clean.

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9.6
Exceptional
144 reviews
Price from
US$250
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
101 reviews
Price from
US$81
per night

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