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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. Amazing place.... we would like to come back! Great place, amazing views, tasty wine... :-)

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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. Everything was great! Very beautiful hotel territory and surroundings. A spacious room with an excellent bathroom. Friendly staff. Lots of activity options. Great breakfast on the terrace with a beautiful view!

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9.3
Superb
1,211 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
1,240 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. Great scenery, like a fairytale! Close to Siena from where you can visit many places around Tuscany.

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9
Superb
1,073 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
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. Everything. Location was wonderful, very peaceful and calming. The grounds were beautiful

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9.6
Exceptional
151 reviews
Price from
US$186
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. Exceptionally pleasant stay. The accommodation was very elegant, stylish and perfectly clean with lovely touches of artwork. The host was incredibly kind and welcoming, offering great tips and recommendations during our visit of Florence. The breakfast, served in the style of English afternoon tea, was a true highlight – homemade pastries, filled croissants, fresh fruit, juice, and delicious coffee. Thank you once again Giuseppe and Mariko for your care and hospitality. It was really pleasure to meet you!

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9.6
Exceptional
118 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
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. It had everything we needed. I loved the bathroom, the bed is very wide and comfortable,the kitchen is good equiped, a balcony where you can drink your morning coffee. The host is very nice and helpful.

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9.4
Superb
105 reviews
Price from
US$80
per night

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