Holiday Rentals in Chianti Region

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Holiday Rentals in Chianti Region

Exterior
Hu Norcenni Girasole Village
4.0 star property
8.6 out of 10, Excellent, (243)
"The location is really beautiful. There are constant shuttles to transport from one location to other within the property. Nice food options and music on specific days Clean Cabins If you have not booked shuttle from the Figline station to this place- you may have a hard time getting a taxi from the station. I recommend to plan ahead for the commute from the train station to this property."
The price is €53
per night
6 Jun - 7 Jun
Hu Norcenni Girasole Village
Seasonal outdoor pool
Camping Village Il Poggetto
3.0 star property
7.8 out of 10, Good, (25)
"The staff is friendly and helpful. This is a nice place to stay . "
The price is €65
per night
13 Jun - 14 Jun
Camping Village Il Poggetto
Exterior
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
10.0 out of 10, Exceptional, (51)
"We looked at many properties, both online and during a December visit to Chianti. This villa was by far best location we found. Everything was perfect, from our communication with Serena, to the reception by Raffaella, and then a stay in an amazing villa in an amazing setting. We were a group of maximum 9 persons, ranging in age from 20 to 60, and all were pleased with the amenities, especially watching the sunset across the vineyards and hills of Tuscany from the terrace. We will be looking to...
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
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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 €296
per night
22 Jun - 23 Jun
Relais Villa Olmo
Pool
Wonderful villa for 6 guests with private pool, WIFI, A/C, TV, patio and parking
10.0 out of 10, Exceptional, (1)
Wonderful villa for 6 guests with private pool, WIFI, A/C, TV, patio and parking
Outdoor pool, a heated pool, pool loungers
Tailored to you・Villa W/ heated pool & concierge service 8 miles from Florence
10.0 out of 10, Exceptional, (85)
"Caterina and her family hosted us and made our trip unbelievable! They helped with transportation, travel ideas, and also prepared home cooked amazing meals in the villa, including two 4 course dinners and an amazing pizza night in the homes built in pizza oven. The grounds are absolutely gorgeous. Thank you for a wonderful stay! I’d definitely stay at this wonderful home again! Thank you Cate!"
Tailored to you・Villa W/ heated pool & concierge service 8 miles from Florence
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
Front of property – evening/night
Villa Il Palagio
8.6 out of 10, Excellent, (24)
"A great suite. Reception can help with taxis to and from the local train station. Fast trains to Firenze / Florence. Restaurant only open for breakfast during the low season, so dinner is a bit of a mission: Reception helped with ordering pizza 🍕"
The price is €140
per night
2 Jun - 3 Jun
Villa Il Palagio
Interior detail
Castello di Montegufoni
7.8 out of 10, Good, (19)
"Great location, great service, great facilities. Unfortunately not wifi signal in rooms. Not reataurant for breakfast. "
Castello di Montegufoni
Outdoor pool, pool umbrellas, pool loungers
Chianti Village Morrocco
3.0 star property
8.6 out of 10, Excellent, (85)
"The staff gave us wonderful tips and suggestions for the area"
The price is €126
per night
27 May - 28 May
Chianti Village Morrocco
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
Pool
Tara by Interhome
8.8 out of 10, Excellent, (8)
"Beautiful guesthouse! Kitchen had everything we needed. Bigger bath towels would have been better. Difficult to communicate with the landlords as they had no English and I had very little italian"
Tara by Interhome
Property grounds
House consists of a "two-room" and a "trilocale", Valdarno Aretino
10.0 out of 10, Exceptional, (44)
"This is a well contained villa with a beautiful garden surrounding the property. As a group of friends we enjoyed all the comforts of the property including the swimming pool. Spent relaxing times in the porch beside the kitchen. The bedrooms are well furnished and clean. The kitchen is well equipped. The hosts Santa and Giovanni are lovely and stocked the kitchen with complimentary essentials and drinks. They also provided some vegetables from their allotment which was very kind of them. We...
House consists of a "two-room" and a "trilocale", Valdarno Aretino
Property grounds
Villa with large garden in the Chianti hills
9.4 out of 10, Exceptional, (62)
"Had a great stay here and met the lovely Ben and his beautiful garden :) plus the 4 local cats hanging around :) great base for us to drive and explore the area :) would definitely stay again at this property."
Villa with large garden in the Chianti hills
Indoor pool, 3 outdoor pools, pool umbrellas, pool loungers
Villa Norcenni Aparthotel
2.0 star property
7.6 out of 10, Good, (14)
"It was clean and safe."
The price is €56
per night
2 Jun - 3 Jun
Villa Norcenni Aparthotel
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Relais Villa Belvedere
9.2 out of 10, Wonderful, (58)
"Absolutely amazing property! The apartment was very comfortable, very clean, smelled good, and beautifully decorated. The breakfast buffet service was EXCELLENT! Wonderful variety and very delicious. Will definitely recommend to family, friends, and will try to stay here again myself. The property has easy access to autostrada as well."
The price is €194
per night
27 May - 28 May
Relais Villa Belvedere
Property grounds
Red House -- Country villa in Chianti Classico
9.8 out of 10, Exceptional, (101)
"The little red house is a wonderful place to completely relax and enjoy the Tusan/Chianti countryside. Very secluded and quiet. Easy access to dining options. Our host, Stefano, was very helpful and replied quickly to any questions."
Red House -- Country villa in Chianti Classico
Pool
House in a typical village in the heart of Chianti
9.6 out of 10, Exceptional, (59)
"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, (25)
"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
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
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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

View from room
Hotel Ristorante Alcide
4.0 star property
8.0 out of 10, Very good, (362)
"Très bien dans l’ensemble Bel ambiance. Très propre."
The price is €66
per night
2 Jun - 3 Jun
Hotel Ristorante Alcide
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas
Hotel Borgo di Cortefreda Relais
4.0 star property
9.4 out of 10, Exceptional, (336)
"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 €187
per night
29 May - 30 May
Hotel Borgo di Cortefreda Relais
Outdoor pool, pool umbrellas, pool loungers
Villa I Barronci Resort & Spa
4.0 star property
9.2 out of 10, Wonderful, (296)
"This mini resort is a must stay. The experience you receive from the second you step on the resort to the end is more than worth its price. Felt extremely welcomed by the staff from start to finish. Stunning views. Nice clean rooms. Great included breakfast. Very good restaurant with drinks and snacks available for purchase throughout the day. Only downside could be kids being allowed or not much to walk to off the resort. "
The price is €209
per night
2 Jun - 3 Jun
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.

Everything you need to know about Chianti Region holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chianti Region holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chianti Region holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chianti Region holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chianti Region. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chianti Region holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chianti Region holiday rentals we have selected for you start as low as €53 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chianti Region rentals

At Expedia, we put the best Chianti Region holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chianti Region rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chianti Region holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chianti Region. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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