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Vacation Rentals in Chianti Region

Estimated price for 1 night/2 adults

Relais Villa Olmo
Relais Villa Olmo
Via Imprunetana Per Tavarnuzze 19, Villa l'Olmo, Impruneta, FI
CA $116
4.7/5 (161 reviews)

Beautiful property and excellent service and great on property restaurant. Staff went above and beyond to make sure we had a great start to our vacation. Would definitely recommend this place to others for a great local place with relaxing atmosphere and great views!

Reviewed on Oct. 12, 2018
This family-friendly Impruneta residence is located in a rural location, 2.9 mi (4.7 km) from Circolo Golf Ugolino, and within 9 mi (15 km) of Pitti Palace and ...
Podere il Pino
Podere il Pino
Localita Il Pino, n. 5, Poggibonsi, SI
4.6/5 (11 reviews)

Let’s start with the good: lots of communication and the lady was very kind and helpful. Beautiful views and peaceful. It was nice to look out and see green EVERYWHERE!! The perfect place to relax. The pool is so refreshing and clean. Our kids didn’t leave it. Ok. We didn’t either lol. Grapevine ...

Reviewed on Jun. 30, 2019
This family-friendly Poggibonsi apartment building is located in a rural location, 3.1 mi (4.9 km) from Church of San Lorenzo, and within 6 mi (10 km) of Archeodromo ...
Podere Vigliano
Podere Vigliano
CA $131
5.0/5 (4 reviews)

The villa at Podere Vigiliano was amazing! Niccolo was incredibly helpful with recommendations for food, activities, and even wine shops, and the apartment itself was better than anticipated. The region is also so beautiful. We would happily stay again.

Reviewed on Oct. 16, 2019
Situated in a rural location, this apartment building is within 9 mi (15 km) of Cantina Antinori, Passignano Abbey and Castello della Paneretta. San Gimignano ...
Camping Village Internazionale Firenze
Camping Village Internazionale Firenze
3.0 out of 5.0 Via San Cristofano, 2, Bottai, Impruneta
3.7/5 (37 reviews)

Our room was on a steep hill and access was extremely difficult especially as I am mobility impaired. The temp was very high and air conditioning in our room was not working. Somebody came to fix it and told us that the problem was solved. However the problem remained as the room was filled with ...

Reviewed on Jun. 17, 2019
Situated in Impruneta, this golf campsite is 0.9 mi (1.4 km) from Florence Charterhouse and 3 mi (4.8 km) from Boboli Gardens. Porta Romana is 3 mi (4.8 km) ...
Fattoria Pratale
Fattoria Pratale
4.4/5 (25 reviews)

We had 4-5 days here and they were excellent.. The weather was a little off but when you are in Tuscany weather is meaningless! And the storms and mist added to the raw beauty. We loved the relaxation Fattoria Pratale offered; the kitchen was perfectly equiped to make breakfast and dinner.

Reviewed on Oct. 7, 2015
This family-friendly Barberino Tavarnelle apartment building is within 3 mi (5 km) of Abbey of Passignano and Passignano Abbey. Santa Lucia al Borghetto Church ...
Riserva di Fizzano Residence
Riserva di Fizzano Residence
3.0 out of 5.0 Localita Fizzano, Castellina in Chianti, SI
5.0/5 (4 reviews)

The location was unique also the setup was amazing it was like the paradise period!

Reviewed on Oct. 3, 2018
Located in a rural location, this family-friendly residence is within 9 mi (15 km) of Casa Vinicola Luigi Cecchi, Archeodromo di Poggibonsi and Magione Castle. ...
Fattoria Querceto
Fattoria Querceto
3.1/5 (8 reviews)

The place is all Tuscany like. The views from our room are gorgeus . The problems were too many. The room was sopposed to have a balcony , and it did not . There is a lot of confort missing in the room . Too dark inside at night , we had to keep moving lamps from the bedroom to the kitchen. The plastic ...

Reviewed on Oct. 28, 2013
This family-friendly Barberino Tavarnelle apartment building is located in a rural location, 2.7 mi (4.4 km) from Cantina Antinori, and within 6 mi (10 km) of ...
Podere San Filippo
Podere San Filippo
CA $147
5.0/5 (20 reviews)

Amazing location over looking vineyards. Very private with pool and activities for families.

Reviewed on Jul. 12, 2019
This family-friendly Barberino Tavarnelle apartment building is located in a rural location, 2.2 mi (3.5 km) from Santa Lucia al Borghetto Church, and within ...
Fontebussi Tuscan Resort
Fontebussi Tuscan Resort
4.4/5 (41 reviews)

Really enjoyed our stay at Fontabussi Beautiful food enjoyed our dining at the restaurant all staff across the board very helpful and pleasant ! We would definately love to come back again .

Reviewed on Sep. 3, 2016
This family-friendly Cavriglia apartment building is located in a rural location, within 3 mi (5 km) of Valdarno, Gianfranco Carla Fineschi Botanical Rose Garden ...
Map

Any good vacation involves wine, and a trip to Chianti, Italy, is no exception. In fact, this central region in Tuscany is known for its superb vineyards, inviting enoteche (wine bars), and of course, the variety of wine named after the territory itself. While wine flows like water in this area, there is more to do than just grape-influenced activities. See for yourself when you book one of our vacation rentals in Chianti, which offer the perfect opportunity to experience the area like a local. Instead of staying in a hotel with hundreds of tourists, you can get to know the town like an Italian citizen.

With the keys to your private rental in Chianti, you’re unlocking your Italian adventure. Drop off your luggage and settle in—open the curtains, kick off your shoes, and start planning your itinerary. If getting a taste of the famous vino is at the top of your list, then a wine tour is a must. Visit the wineries, learn about the local history, and sample the local varieties. Once you’ve sipped your way through the region, make room in your belly for olives and olive oil that come straight from the grove. There’s more to this region then just pleasing your palate, though—explore the Saturday market in the plaza at Greve, check out the Archeological Museum of Chianti Senese, and make your way to the Chianti Sculpture Park. After your adventures in the wine country, head back to the best of Chianti vacation rentals and rest up for the next day’s activities.

When it comes to finding short-term apartment rentals in Chianti, Expedia makes it easier than ever. Take a peek at our vast selection, pick your dates, and make your reservation. You can also contact the property manager to make additional arrangements after booking. Pack your bags and prep your palate: Chianti is waiting.

Other types of properties in Chianti Region you may be interested in

Estimated price for 1 night/2 adults

COMO Castello Del Nero

COMO Castello Del Nero

  • Free Cancellation
  • Reserve now, pay when you stay
5.0 out of 5.0
 
 

COMO Castello Del NeroCA $487

Nov. 3 - Nov. 4

COMO Castello Del NeroCA $487
Locanda le Piazze

Locanda le Piazze

Localita Le Piazze 41, Castellina in Chianti, SI
  • Free Cancellation
  • Reserve now, pay when you stay
4.0 out of 5.0
 
 

Locanda le PiazzeCA $224

Nov. 1 - Nov. 2

Locanda le PiazzeCA $224