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The best vacation rentals in Chianti

Check out our selection of great vacation rentals in Chianti

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Wonderful: 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
Wonderful
1,007 reviews
Price from
$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. Great team, friendly and spot on with help and advice! Just amazing breakfast and convenient location!!

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9.3
Wonderful
1,210 reviews
Price from
$225
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. Wonderful and peaceful surrounding. Beautiful care was taken of all of us during our stay. The rooms are very nicely furnished and the sitting area outside is just gorgeous. Pool outstanding and very clean surrounded by olive trees. You also have to try cantuccini il santo, delicious.

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9.3
Wonderful
1,236 reviews
Price from
$92
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
Wonderful
1,084 reviews
Price from
$175
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
Wonderful
115 reviews
Price from
$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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9.1
Wonderful
139 reviews
Price from
$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. Our whole trip was amazing. The accommodation and the surroundings were gorgeous. It was everything we hoped for. I would especially like to thank Paolo, who took excellent care of us. He provided us with breakfast, bicycle rental and booked great wine tasting for us. We were extremely satisfied and will definitely come again. Thank you !

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9.6
Exceptional
147 reviews
Price from
$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. 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
$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. Staff were very helpful and obliging. Lovely extra touches with breakfast offerings and bottle of wine. Assisted us with meal reservations and recommendations. Highly recommend. Pool area lovely.

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9.6
Exceptional
146 reviews
Price from
$248
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
Wonderful
102 reviews
Price from
$80
per night

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