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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. Fattoria di Cinciano is a hidden gem in the Tuscan countryside. Perfectly positioned on a hilltop among olive groves and vineyards, it offers both peaceful seclusion and convenient access to nearby towns and attractions. Our apartment was spacious, comfortable, and well-equipped, making it feel like a home away from home. The estate features beautiful gardens and stunning views of the rolling Tuscan hills. The friendly staff provided excellent recommendations for local restaurants and activities, enhancing our experience of the region. What we appreciated most was the tranquil atmosphere - ideal for unwinding and experiencing the authentic charm of Tuscany. Highly recommended for anyone seeking a relaxing Italian countryside getaway with all the comforts.

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9.3
Superb
1,010 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. Location and views are second to none, but would never be the same if not for the excellent staff working there. Piero (wonderful wine and olive oil tasting), Vicenzo and Alesso at the restaurant were amazing and no less amazing were Lorenzo, Sophie and two other ladies at reception that i can't remember her names (sorry!) but equally super professional and accommodating!

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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. Location,ambient and surroudings were amazing.

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9.3
Superb
1,244 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. A lovely view to hilly neighbourhood, great restaurant with delicious food and flowers on the table. Very comfortable and cozy rooms.

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9
Superb
1,087 reviews
Price from
US$176
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$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. Lovely property in keeping with the location

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9.6
Exceptional
145 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. Everything! Very nice family, excellent breakfast, almost everything homemade, very neat room, take one with air conditioning because it is very hot in Italy. You can ask them anything, father knows the beautiful places in Tuscany and tells you where you can go (if you want of course).

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9.7
Exceptional
111 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. 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
143 reviews
Price from
US$249
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$80
per night

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