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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. Beatiful place in a very romantic scenery. Delicious breakfasts made of local products, really good wines and great restaurant. We had a wonderful stay!

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9.3
Superb
1,008 reviews
Price from
US$163
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. it is my go-to gem in Tuscany, it was my third time in this hotel and i cannot wait to be back. although it is in a old and traditional Tuscan building, the rooms are very modern, spacious, well equipped and very clean. it is luxurious, quite, elegant with high quality service, amazing food and great amenities.

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9.3
Superb
1,209 reviews
Price from
US$206
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. The staff, the views, the wine tour with the owner, central to many Tuscany ‘s town

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9.3
Superb
1,236 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. 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
1,081 reviews
Price from
US$141
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
116 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
140 reviews
Price from
US$69
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. Entering the gates of Corte del Chianti was like a dreamland. Everything was perfect, the room, the gardens, the pool, the facilities. Everything is new or refurbished, the bed extremely comfortable, the views extraordinary and everything is very clean. The hosts were very friendly and helpful. We highly recommend it to anyone who wants to spend some quiet and relaxed time.

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9.6
Exceptional
147 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. Beautiful backyard with a view of the surrounding nature of Tuscany. Have homemade breakfast while hearing the birds with a super friendly couple. Ask about restaurant recommendations and you will get the best out of your trip, with actual traditional cuisine and at reasonable prices.

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9.6
Exceptional
116 reviews
Price from
US$142
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. The apartment was pristine clean and spacious with a large terrace outside. The pool is amazing! Perfect place of quite relax surrounded by Tuscan nature.

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9.6
Exceptional
146 reviews
Price from
US$216
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. We chose the apartment for its location (close to all the Tuscan attractions) and ended up falling in love with the beauty of the apartment – modern, clean, and everything you could wish for, plus a very friendly owner.

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9.4
Superb
103 reviews
Price from
US$80
per night

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