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Poggibonsi
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 apartment on a little hill with breathtaking view! Just perfect and highly recommendable. We will return for sure!
San Casciano in Val di Pesa
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 place is amazing, the rooms are great, the views breathtaking and the staff wonderful
Gaiole in Chianti
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 is an excellent guest house. The owners are wonderful. The room is wonderful. And the wine tasting is perfect. I hate Chianti. I love Chianti Classico. You can figure that out when you get there. The drive to the hotel is a bit of fun if you like hill driving and the village is unreal. You cannot miss in San Sano. We will be back with friends. You should, too.
San Donnino
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. Everything is great, ,Alessandra and her family are amazing, they make sure that you have everything that you need. The nature and the location is also great.
Colle Val D'Elsa
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.
Staggia
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
Gaiole in Chianti
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. The warmth of the hosts, the peace of the surroundings and the gorgeous pool
Gaiole in Chianti
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. Friendly team, beautiful location, they’ve thought everything.
San Casciano in Val di Pesa
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.
Greve in Chianti
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. Location, cleanliness, the view!
 
Holiday Rental in Impruneta
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Holiday Rental in San Casciano in Val di Pesa
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Holiday Rental in Poggibonsi
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Holiday Rental in Vagliagli
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Holiday Rental in Impruneta
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Many families visiting Chianti loved staying at B&B Antiche Rime, Capannelle Wine Resort and Laura Chianti Vacanze.
Similarly, La Corte del Chianti Classico, Corte Di Valle and Villa Di Capovento are also popular among family travellers.
Palazzo Galganetti Betti, Borgo Argiano and La Valletta Boutique Wine Estate have received great reviews from guests in Chianti regarding the views from these holiday rentals
Guests staying in Chianti also spoke highly of the views from these holiday rentals: Villa la torre, Il Poderino and Villa Di Capovento.
The average price per night for a holiday rental in Chianti for this weekend is US$197, based on current Booking.com prices.
Most holiday rentals on Booking.com offer free cancellation.
There are 1,066 holiday rentals in Chianti you can book on Booking.com.
We make it quick and easy to book a holiday rental in Chianti. Here’s what we offer:
• Free cancellation on most stays
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Couples travelling in Chianti loved staying at Villa Di Capovento, Tenuta Tegolato and Borgo Argiano.
Similarly, these holiday rentals in Chianti are highly rated by couples: Corte Di Valle, La casa di Arianna and Agriturismo Melariano.
Agriturismo San Sano, Fattoria di Cinciano and Salvadonica are some popular holiday rentals in Chianti.
In addition to these holiday rentals, Borgo Argiano, Villa Di Capovento and Corte Di Valle are also popular in Chianti.
Spectacular location in an abandoned old village on top of a hill among vineyards. Amazing swimming pool with lots of sun beds and umbrellas with beautiful views. Spacious and air-conditioned suites (must have in summer time). Additional self-service available (laundry, iron & iron board, coffee pods). The owner provided a list of local restaurants and shops, which was very convenient and helpful to start your stay. Well regarded privacy of the guests.
The beautiful views of vineyards and hills, we felt very welcome and on vacation. The appartment on two storeys was well decorated and the swimming pool very refreshing with a stunning view. Wow Tuscany at its best. The owners and their friendly dog were also nice. The village is closeby to get the grocery and that's where you do the check-in before arrival.
Big and clean swimming pool, well-equipped house, great spot if you want to visit local towns and villages in Toscania. Each family has their own patio and even grill. Great contact with the owned who will respond to all your questions. My tip is to follow Elisa's directions instead of GPS (beacuse of Google Maps, i ended up on impassable, rocky road)
Stunning villa, big room, loved the pool area and lots of sitting areas outdoors. Very relaxing and quiet.
Its a piece of Tuscan paradise, run by a highly professional, friendly and competent family, set in a 1000 year old village with its own Church. Breathtaking beauty, style and harmony.
An excellent, spacious, and lovely villa set in a pastoral and peaceful location. The kitchen is fully equipped, and there's a nice patio. The owners, Serena and her parents, are warm and hospitable. Generally, everything was great. The only suggestion would be a stronger shower water current to make it perfect.
Property is vast and full of vineyards , very clean, organised and welcoming. Staff is very friendly and willing to help on every request. Wine tasting is definitely recommended! Great breakfast and comfortable rooms! We got exactly what we wanted and that is a cozy family feeling of a Tuscany villa! They do offer Vespa rentals and with enough planning ahead you can have yours to drive around this beautiful piece of Tuscany.