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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. The place is completely peaceful and truly idyllic; they have preserved the old Italian charm.

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9.3
Superb
1,010 reviews
Price from
US$160
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 property itself was very nice and pleasant, specially the staff.

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9.3
Superb
1,180 reviews
Price from
US$118
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
Superb
1,260 reviews

Situated within 25 km of Piazza Matteotti and 36 km of Piazzale Michelangelo, La Pimpinella di Semifonte features rooms with air conditioning and a private bathroom in San Donnino. This property offers access to a terrace and free private parking. The farm stay has family rooms. The stay was exceptional. Nestled in the middle of greenery, the grounds are kept exceptionally tidy. Alessandra and her husband are so welcoming and attentive to anything you need. The food was amazing, and they had different dishes that we hadn't seen on other menus. We were also lucky enough to stay while a gentleman prepared fresh mozzarella before dinner. The room was clean and had everything we needed to enjoy our stay. We did small day trips to the nearby villages but could have easily stayed there all day relaxing by the pool.

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9.8
Exceptional
106 reviews
Price from
US$150
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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9.5
Exceptional
122 reviews
Price from
US$159
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
150 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. Incredible place and very friendly owners, highly recommend the place!

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9.7
Exceptional
163 reviews

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. We rented an apartment with two couples as we attended a wedding close by - the place was great in so many aspects, very spacious and freshly renovated apartments, nice pool, very calm with great view and super friendly and accommodating team.

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9.6
Exceptional
155 reviews
Price from
US$212
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
110 reviews
Price from
US$79
per night

Situated 28 km from Ponte Vecchio, 28 km from Uffizi Gallery and 28 km from Piazzale Michelangelo, Bonaventura features accommodation located in Greve in Chianti. The property is around 30 km from Piazza della Signoria, 30 km from Cathedral of Santa Maria del Fiore and 30 km from Piazza del Duomo di Firenze. Free WiFi is available throughout the property and Piazza Matteotti is 1.5 km away. An idyllic Tuscan location. The view from the window was like from a postcard. Old town house in the most charming village- one wants to take à picture on every corner. Stylish, clean and spacious apartment, equipped with everything one needs. Friendly and helpful host.

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9
Superb
127 reviews
Price from
US$115
per night

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