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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 views, extremely clean, comfortable facilities

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9.3
Superb
1,011 reviews
Price from
US$162
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. It’s always an amazing resort, the scenery, the rooms, everything is amazing

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9.3
Superb
1,211 reviews
Price from
US$119
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. This place is in a great location for exploring the Chianti Classico region, yet in a quite remote village. It is beautiful here, the house, the pool, the landscape is gorgeous! Everyone was very friendly and helpful! The breakfast was good. We really liked the tour of the vineyard and cellar and the tasting of their wines. They are so wonderful, we bought some to bring home. Seriously recommend this place for everyone who wants to explore around and stay at a peaceful place.

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9.4
Superb
1,231 reviews
Price from
US$81
per night

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 property is amazing, well-taken care of and absolutely beautiful. The staff is super friendly, helpfu, welcomingl and accommodating and makes you feel at home.

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9.8
Exceptional
105 reviews
Price from
US$151
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
119 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
144 reviews
Price from
US$66
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. We recently had the pleasure of staying at La Corte del Chianti, and it was an experience we'll never forget. Nestled in the heart of the picturesque Chianti region, the location is nothing short of perfect. Surrounded by rolling vineyards and breathtaking views, it’s the ideal spot for anyone looking to immerse themselves in the serene beauty of Tuscany. The cleanliness of the property was impeccable. Every corner of La Corte del Chianti was meticulously maintained, offering a comfortable and pristine environment that made us feel right at home. The room was spacious, tastefully decorated, and provided all the modern comforts one could wish for, while still retaining a charming rustic appeal. What truly set this place apart, however, were the incredible hosts. From the moment we arrived, they went above and beyond to ensure our stay was nothing short of perfect. Their warmth, attentiveness, and local knowledge made the entire experience even more enjoyable. Whether it was recommending the best local restaurants, suggesting tours, or simply offering a friendly chat, they made us feel like cherished guests.

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9.6
Exceptional
160 reviews
Price from
US$242
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. We liked this structure and felt at home because of our host, Giuseppe and Mariko-san. The structure is a villa-style B&B with an east-facing garden where you can enjoy breakfast or simply relax and take in the fresh air. Our room is pretty clean and cozy with everything well maintained and working perfectly, which made us feel at ease especially after a tiring day in the city. The location of the hotel is close to the city center which is about a 30 min bus ride. We mainly visited Florence based on the map with routes that ​​Giuseppe recommended. If you have a car, you can also explore more brilliant views in Sienna, Pizza, etc. Giuseppe and Mariko-san served us a full Italian-style breakfast with a genuine warmth everyday. We enjoyed it in the garden while appreciating the Tuscan landscape and sunshine, or in the tidy and fully equipped kitchen when it rained. They offered us a great amount of help, even though they didn’t have to. We arrived late the first day getting there without carrying any food. We were moved when Giuseppe kindly offered to not only translate the menu but also order the pizzas for us. Mariko-san looked up the bus timetable so that we could be well prepared the next day to Florence. What’s more, Giuseppe also set up tables with everything we needed and helped us warm up the food. Thanks to their hospitality, we had a wonderful time there. We would love to come back sometime and recommend it to our friends. Maybe next time we’ll have the chance to see Naomi in person :)

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9.6
Exceptional
121 reviews
Price from
US$141
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. Property is nice and quite and clean.

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9.6
Exceptional
152 reviews
Price from
US$215
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
107 reviews
Price from
US$80
per night

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