Chianti Region Holiday Rentals

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Holiday Rentals in Chianti Region

Hu Norcenni Girasole Village
Exterior
Hu Norcenni Girasole Village
4.0 star property
8.6 out of 10, Excellent, 246 reviews
"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 NZ$89
per night
2 Jun - 3 Jun
Hu Norcenni Girasole Village
Camping Village Il Poggetto
Seasonal outdoor pool
Camping Village Il Poggetto
3.0 star property
7.8 out of 10, Good, 25 reviews
"Absolutely beautiful! The property was beautiful the views were amazing the dining was delicious the cabin was exceptionally clean!"
The price is NZ$139
per night
2 Jun - 3 Jun
Camping Village Il Poggetto
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Exterior
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
10.0 out of 10, Exceptional, 51 reviews
"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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Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
Pool
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
9.4 out of 10, Exceptional, 56 reviews
"The biggest issue that I had was the information that I received about the bus was totally misleading . It says there is a bus down the street… it’s a 10-15 min walk. Oh and it only comes 2-3 times a day and forget about getting back there on the bus. So 1/2 of us came unprepared to rent a car. You must have a car unless you don’t plan on leaving. I can tell you a cab will come and pick you up, the one way trip to Santa Maria Novella is @ 70-80 euro per cab. We could fit 4-6 people and the fee...
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
Relais Villa Olmo
Aerial view
Relais Villa Olmo
9.4 out of 10, Exceptional, 186 reviews
"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 NZ$523
per night
22 Jun - 23 Jun
Relais Villa Olmo
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City
Outdoor pool
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City
9.8 out of 10, Exceptional, 84 reviews
"Staying at a villa and property like this was a dream come true. As you’ve read the pictures just do not do it justice. The view is spectacular. Our host was so charming and helpful. We had a cooking class with Jacopo from "Let's Cook" which was so much fun. We also did a Chianti Wine and Food Safari with Walkabout tours that was fantastic. All of Caterina suggestions were so helpful even down to the drivers she recommended. Having this Villa to come home to each night was the icing on the cake."
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City
Tailored to you・Villa W/ heated pool & concierge service 8 miles from Florence
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 reviews
"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
House with character in typical medieval borgo on the Chianti Classico hills
Property grounds
House with character in typical medieval borgo on the Chianti Classico hills
9.6 out of 10, Exceptional, 44 reviews
"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
Villa Il Palagio
Front of property - evening/night
Villa Il Palagio
8.6 out of 10, Excellent, 24 reviews
"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 NZ$227
per night
10 Jun - 11 Jun
Villa Il Palagio
Castello di Montegufoni
Interior detail
Castello di Montegufoni
7.8 out of 10, Good, 19 reviews
"Great location, great service, great facilities. Unfortunately not wifi signal in rooms. Not reataurant for breakfast. "
Castello di Montegufoni
Glicini 3, your holiday home in Chianti just 30 minutes from Florence and Siena
Outdoor pool
Glicini 3, your holiday home in Chianti just 30 minutes from Florence and Siena
10.0 out of 10, Exceptional, 47 reviews
"Amazing villa. Everything is clean and beautiful. Pleasure to be there. Highly recommend."
Glicini 3, your holiday home in Chianti just 30 minutes from Florence and Siena
Chianti Village Morrocco
Outdoor pool, pool umbrellas, pool loungers
Chianti Village Morrocco
3.0 star property
8.6 out of 10, Excellent, 85 reviews
"The staff gave us wonderful tips and suggestions for the area"
The price is NZ$223
per night
31 May - 1 Jun
Chianti Village Morrocco
Yellow House Country Villa in Chianti Classico
Property grounds
Yellow House Country Villa in Chianti Classico
10.0 out of 10, Exceptional, 89 reviews
"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
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
Outdoor pool
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
10.0 out of 10, Exceptional, 89 reviews
"We had 3 families, 14 people total, who have been life long friends visiting Italy and I can not put into words how great our experience was. The house was amazing. Convenient to Florence and the small towns around Florence. Lots of room, incredibly clean and comfortable. However, what really made the trip so special were our hosts, Beatrice and Jacopo. From the breakfast every morning, to the welcome dinner, cooking class and last night in Florence BBQ, they exceeded all expectations. I...
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
Farmhouse in the heart of the real chiantishire
Exterior
Farmhouse in the heart of the real chiantishire
10.0 out of 10, Exceptional, 125 reviews
"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
Happy holidays in Chianti, between olives and vines, 35 min. From Florence
Property grounds
Happy holidays in Chianti, between olives and vines, 35 min. From Florence
10.0 out of 10, Exceptional, 13 reviews
"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
House consists of a "two-room" and a "trilocale", Valdarno Aretino
Property grounds
House consists of a "two-room" and a "trilocale", Valdarno Aretino
10.0 out of 10, Exceptional, 44 reviews
"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
Villa with large garden in the Chianti hills
Property grounds
Villa with large garden in the Chianti hills
9.4 out of 10, Exceptional, 63 reviews
"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
Villa Norcenni Aparthotel
Indoor pool, 3 outdoor pools, pool umbrellas, pool loungers
Villa Norcenni Aparthotel
2.0 star property
7.6 out of 10, Good, 14 reviews
"It was clean and safe."
The price is NZ$99
per night
2 Jun - 3 Jun
Villa Norcenni Aparthotel
Relais Villa Belvedere
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Relais Villa Belvedere
9.2 out of 10, Wonderful, 58 reviews
"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 NZ$353
per night
16 Jun - 17 Jun
Relais Villa Belvedere
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See all available properties in Chianti Region
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

Hotel Ristorante Alcide
View from room
Hotel Ristorante Alcide
4.0 star property
8.0 out of 10, Very good, 362 reviews
"Good"
The price is NZ$106
per night
31 May - 1 Jun
Hotel Ristorante Alcide
Hotel Borgo di Cortefreda Relais
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 reviews
"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 NZ$349
per night
3 Jun - 4 Jun
Hotel Borgo di Cortefreda Relais
Villa I Barronci Resort & Spa
Outdoor pool, pool umbrellas, pool loungers
Villa I Barronci Resort & Spa
4.0 star property
9.2 out of 10, Wonderful, 296 reviews
"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 NZ$336
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chianti Region holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chianti Region. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chianti Region. Seeing all the best attractions is bound to make you fall in love with Chianti Region. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chianti Region short-term rentals, that won’t be hard to do.

Recent reviews of Chianti Region properties
Expedia verified reviews

Castello Vicchiomaggio

Castello Vicchiomaggio

5/5 Excellent
"Great friendly staff. Beautiful view from the property. Great location to explore Tuscany. We would definitely return again. The wine was good as well. "
A verified traveller stayed at Castello Vicchiomaggio
Posted 4 days ago
Castello Vicchiomaggio