Chianti Region Vacation Rentals

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Vacation Rentals in Chianti Region

Exterior
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
10.0 out of 10, Exceptional, (49)
"We cannot recommend this villa highly enough!! There are no words to fully describe the beauty of Isola Serena. The main villa & new guesthouses, along with the outdoor spaces, were so thoughtfully and beautifully restored - the property was both luxurious and authentic to Tuscan style. It was easily the most beautiful place we have ever had the opportunity to stay, with views that almost seemed like they couldn't be real! The hosts, Serena and Peter, were so kind and communicative before &...
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Pool
Wonderful villa for 6 guests with A/C, WIFI, private pool, TV, patio and parking
10.0 out of 10, Exceptional, (1)
Wonderful villa for 6 guests with A/C, WIFI, private pool, TV, patio and parking
Outdoor pool, a heated pool, sun loungers
Tailored to you・Villa W/ heated pool & concierge service 8 miles from Florence
10.0 out of 10, Exceptional, (84)
"I can’t begin to describe how amazing this trip was. Cate was the most amazing host. She arranged so many events, dinners, transportation that made our trip seamless. Her sister was also very helpful. We did pizza making, florentine steak dinner, and pasta making which were all great. Valentina was our guide for pasta and pizza. The villa was perfect for our group of eight."
Tailored to you・Villa W/ heated pool & concierge service 8 miles from Florence
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Outdoor pool
Glicini 3, your holiday home in Chianti just 30 minutes from Florence and Siena
10.0 out of 10, Exceptional, (46)
"Large three-bedroom, three-bathroom apartment with a nice layout. The description on VRBO does not make it clear that you are only getting an apartment in a building that includes two other apartments. I thought I was booking a house. We stayed four days when the weather was not that cold, but we needed the heating, for which there is a separate charge. For four days, we spent another 100 euros. The apartment was clean and the linens and towels were of good quality. The appliances, pots and...
Glicini 3, your holiday home in Chianti just 30 minutes from Florence and Siena
Property grounds
Yellow House Country Villa in Chianti Classico
10.0 out of 10, Exceptional, (89)
"A beautiful house for nature lovers , we had everything we needed for our stay. The owner was very friendly and helpful. We really enjoyed our time there . The road to the house was a little bit rough , it could be difficult with a small car . Stefano Grazie per tutti!"
Yellow House Country Villa in Chianti Classico
Outdoor pool
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
10.0 out of 10, Exceptional, (87)
"The owners of this property take great care and pride in keeping the property neat and clean and in keeping the renters happy. They helped us with our last minute changes, and we had a large group. Fantastic Rental."
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
Exterior
Farmhouse in the heart of the real chiantishire
10.0 out of 10, Exceptional, (125)
"This charming farmhouse made our stay in the Tuscan region perfect. While we never met the host, they were very easy to communicate with and responded quickly. The farm and area is beautiful! We rented a car and did day trips to Montepulciano, Siena, Volterra, Lucca and Cinque Terre. The house is also convenient to the local town. We found excellent restaurants and also bought groceries at the Coop. Would highly recommend staying here if planning a trip to this region of Italy."
Farmhouse in the heart of the real chiantishire
Property grounds
Happy holidays in Chianti, between olives and vines, 35 min. From Florence
10.0 out of 10, Exceptional, (13)
"The humble studio is very charming and perfect for singles or couples that like a quiet and peaceful Holiday. The cabin is small but practical and has everything you need. The garden is spacious and beautiful, with a fantastic view on the hills and we always had a nice breeze and shade in front of door. The pool is large and clean and the Landlady was very friendly and helpful at all times. The location is fantastic, ideal if you want explore Tuscany by car and also great if you just like to...
Happy holidays in Chianti, between olives and vines, 35 min. From Florence
Property grounds
House consists of a "two-room" and a "trilocale", Valdarno Aretino
10.0 out of 10, Exceptional, (43)
"Siamo voluti tornare nuovamente per un altro capodanno, soprattutto grazie all'esperienza fantastica che abbiamo vissuto l'anno scorso. La casa è impeccabile come sempre, fornita di qualsiasi cosa e soprattutto pulita. Ci teniamo ancora una volta a ringraziare i proprietari, che hanno soddisfatto le nostre richieste e che hanno saputo aiutarci nel momento del bisogno. Io e i miei amici siamo ancora più soddisfatti dello scorso anno!"
House consists of a "two-room" and a "trilocale", Valdarno Aretino
Property grounds
Villa Andrei, a relaxing bath in the Tuscan countryside with private pool
10.0 out of 10, Exceptional, (46)
"View and property were perfect and met expectations"
Villa Andrei, a relaxing bath in the Tuscan countryside with private pool
Fridge, microwave, oven, stovetop
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
10.0 out of 10, Exceptional, (1)
"Enjoyed it"
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
Outdoor pool
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City
9.8 out of 10, Exceptional, (83)
"Just a first class villa with everything you might wish for: a great country setting and nicely tucked away from the hustle and bustle of Florence - yet close enough (with a car) to make daily visits."
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City
Property grounds
Red House -- Country villa in Chianti Classico
9.8 out of 10, Exceptional, (100)
"The Red House was a quiet and great place from which to tour the Chianti towns and to use as a base to visit Florence and Siena. It is a great position as it is 30minutes from both by car and is 15mins drive to Castellini In Chianti. The house is small but proficiently equipped and our needs were met well by Stefano and Hans. Compared to other properties we are staying in (we are travelling in Italy for 9 weeks), all other houses have not charged extra for gas and electricity- a bit of feedback...
Red House -- Country villa in Chianti Classico
Outdoor pool
Luxury villa with fantastic views, pool, 4 bedrooms, 2 bathrooms
9.8 out of 10, Exceptional, (60)
"This villa was perfect for our stay. It is beautiful, super comfortable (we had 9 adults) and private yet only 10 min drive to a grocery store and cute restaurants. And a great location for day trips to Siena and local wineries. The hosts were easy to communicate with, and we loved our in home dinner prepared by Simona. I cannot recommend this place enough."
Luxury villa with fantastic views, pool, 4 bedrooms, 2 bathrooms
Property grounds
House with character in typical medieval borgo on the Chianti Classico hills
9.6 out of 10, Exceptional, (44)
"A very beautiful property and grounds, in the middle of the Tuscan countryside The patio area with charcoal grill amongst the olive trees was a beautiful setting for snacks and meals The house inside was very rustic and authentic but comfortable and the kitchen and bathroom s are well equipped Our hosts were very friendly and the welcome bottle of wine and fresh fruit basket was a wonderful touch after a long day of travelling The neighbours were lovely we spoke to several of them though a...
House with character in typical medieval borgo on the Chianti Classico hills
Superior Double Room Single Use, 1 Queen Bed, Balcony, Hill View | View from room
Palazzo Pacini
9.6 out of 10, Exceptional, (70)
"The bedroom was small but had a lovely view from the bathroom window and balcony. Breakfast was delicious and staff were friendly. It was disappointing that the room was hot and stuffy even with air-conditioning on (temp 24.5 degrees). We opened the balcony doors which helped however let insects in. It was also disappointing for the price that parking was a few minutes walk from property. "
The price is ￥22,932
￥25,561 total
includes taxes & fees
May 14 - May 15
Palazzo Pacini
Pool
House in a typical village in the heart of Chianti
9.6 out of 10, Exceptional, (58)
"Our stay in this enchanting little village was just perfection. Our renovated “barn” was so cozy and comfortable, Our host, Veronica could not have been more attentive to our needs (it was quite cold when we were there and she made sure we had fuel, etc to stay warm). She also brought us wine and olive oil from her family and a delicious tart. It was peaceful, beautiful and everything we could have hoped for. Thank you Veronica and Massimiliano for sharing your magical little corner of Italy!...
House in a typical village in the heart of Chianti
Pool
House in a typical village in the heart of Chianti
9.6 out of 10, Exceptional, (24)
"A lovely location and friendly hosts who were willing to make the extra effort. It is a small property but with everything you need. It is not the property in the photographs but close to that property. It is a holiday complex with mainly non Italian guests but authentic Castellina in Chianti is a 15 min drive away."
House in a typical village in the heart of Chianti
Pool
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
9.4 out of 10, Exceptional, (54)
"This is a great place to stay with multiple families. You are all together but have your own separate space and kitchen. We stayed here with family and attended our sons wedding nearby!! There is a great restaurant that we drove to not far from the Villa that I highly recommend: Osteria Del Tempo Perso - Montespertoli FI There is a Coop about 15 min drive and 25 min to downtown Florence"
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
Aerial view
Relais Villa Olmo
9.4 out of 10, Exceptional, (186)
"The young lady who checked us in, I believe Gloria was her name, was very sweet and helpful during our stay. She upgraded us to a suite and it was very comfortable except for a dog that barked during the night,apparently, it belonged to the owners who were not on the property. So other than the dog annoying us during the nights and early mornings it was a comfortable place to stay and close enough to Florence to drive to in about 15 to 20 minutes. Just be careful not to be redirected too much...
The price is ￥40,266
￥44,796 total
includes taxes & fees
May 22 - May 23
Relais Villa Olmo
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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

2 restaurants, breakfast served
Borgo Vescine
4.0 star property
9.4 out of 10, Exceptional, (197)
"A perfect stay. Highly recommend. Beautiful place. Tremendous attention to detail by the staff in all areas. Attentive and knowledgeable staff who made you feel special and pampered! Close to drive to all key destinations. Bravo!"
The price is ￥50,214
￥56,242 total
includes taxes & fees
May 24 - May 25
Borgo Vescine
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas
Hotel Borgo di Cortefreda Relais
4.0 star property
9.2 out of 10, Wonderful, (334)
"The food options for vegetarians were few but very delicious. The breakfast spread was excellent. Staff in general were friendly and helpful. The room was clean and comfortable and the views were great. They could improve their gym by replacing or repairing the broken equipment such as the treadmill."
The price is ￥23,424
￥26,606 total
includes taxes & fees
Jun 3 - Jun 4
Hotel Borgo di Cortefreda Relais
Outdoor pool, pool umbrellas, sun loungers
Villa I Barronci Resort & Spa
4.0 star property
9.2 out of 10, Wonderful, (292)
"Hotel is very well situated on top of the hill. You can enjoy the tuscany view while having breakfast, or even having a drink over the restaurant’s terrace. Staffs are very nice, polite, and helpful. "
The price is ￥27,302
￥31,039 total
includes taxes & fees
May 19 - May 20
Villa I Barronci Resort & Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.