Search holiday rentals in Chianti

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. Can’t get over this place! Hands down the most beautiful view in all of Tuscany. We truly wished we had stayed longer. The room was clean, spacious, and incredibly comfortable—they truly thought of everything. It had that nostalgic, insanely pure Tuscan charm we dreamed of. We loved the romantic vibe of the pool and gardens, and the restaurant was absolutely amazing. Every little detail was perfect. And the breakfast? Unreal. So delicious—easily the best we had in Italy—and we were so happy it was included. Loved every second of our stay!

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. We loved everything about this property. The location was beautiful. The rooms were nice and clean. We did eat at the restaurant located on the property. Good food. They provided a appetizer with our wine which was the best green olives I have ever had. They tasted completely different than the States. They have a beautiful setting amongst the vineyards and olive trees. Pool to relax and the view was amazing.

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. Amazing location, everything was picture perfect. Check in/out was smooth, big area to relax. The staff was helpful and gave recommendations. Prior to arrival communication was fast and helpful. I also recommend vinery tour and wine sampling provided by the host.

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 and friendly staff, beautiful location and excellent food. We felt welcome all the time and would love to come back another time.

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.

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

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!

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. This place is a little gem, and I wish we had time to stay longer! It's ideal as a base to go and explore Florence while staying surrounded by nature and quietness, wander through the countryside postcards' views, or simply unwind in their lovely house & garden. The owners truly went above and beyond to ensure that every guest felt welcomed and pampered, and every detail was well looked after. The stylish private room has an independent entrance. It's spacious and super clean, with mosquito nets on the windows. Even without using AC, we enjoyed fresh nights of rested sleep during a hot Italian summer. We particularly enjoyed the mattress and the sheets! Such a pleasure after long days of walking and driving. In the morning, indulge in a delightful breakfast experience! An authentic Italian breakfast featuring delicious homemade cakes, muffins, cookies, and more of the highest quality. It's one of the best we had, enjoyed in their peaceful and charming garden. It was the best way to start the day! Last but not least. Don't forget to ask Giuseppe where to eat and explore during your stay. As a local and well-travelled around the world, he knows all the hidden gems out of the usual tourist traps. We appreciated his insider and valuable tips!

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.

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. We chose the apartment for its location (close to all the Tuscan attractions) and ended up falling in love with the beauty of the apartment – modern, clean, and everything you could wish for, plus a very friendly owner.