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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. Stunning scenery, beautiful traditional and well maintained rooms, great service, good wine and food. We will definitely come back 🤗

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9.3
Superb
1,010 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. The hotel itself is gorgeous in the countryside. We love it and have been repeat guests over the years The calm and views from the hotel grounds Location is close enough to Florence when you want more action or city life

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9.3
Superb
1,209 reviews
Price from
US$139
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
1,238 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. Delicious meals with a beautiful view, lovely location and pool, comfortable room, ample parking

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9
Superb
1,078 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$161
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
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. The warmth of the hosts, the peace of the surroundings and the gorgeous pool

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9.6
Exceptional
148 reviews
Price from
US$182
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. My husband and I stayed at Casa Decimo and we're so thankful to have found this cute B&B. Giuseppe and Mariko (and their daughter Naomi) we're so kind and warm, it made our stay feel like we were with family. Giuseppe had so many recommendations of things to do in the area which we were so grateful for. It was great chatting with him about his travels around the world too! Thank you for the wonderful stay!

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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. Beautiful self-contained cottage. Wish we had stayed longer to explore the area more. We ran late for check-in, and the staff were very helpful and accommodating.

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9.6
Exceptional
147 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. Warm, clean, new and cozy. We would stay again.

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9.4
Superb
103 reviews
Price from
US$80
per night

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