Chianti Region Vacation Rentals

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Vacation Rentals in Chianti Region

Exterior
Hu Norcenni Girasole Village
4.0 star property
8.4 out of 10, Very Good, (237)
"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 $39
$47 total
includes taxes & fees
15 May - 16 May
Hu Norcenni Girasole Village
Seasonal outdoor pool
Camping Village Il Poggetto
3.0 star property
7.8 out of 10, Good, (24)
"The staff is friendly and helpful. This is a nice place to stay . "
Camping Village Il Poggetto
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
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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
Front of property - evening/night
Villa Il Palagio
8.6 out of 10, Excellent, (23)
"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 🍕"
Villa Il Palagio
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
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
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
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
Outdoor pool, pool umbrellas, sun loungers
Chianti Village Morrocco
3.0 star property
8.6 out of 10, Excellent, (84)
"The staff gave us wonderful tips and suggestions for the area"
Chianti Village Morrocco
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
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
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
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...
Relais Villa Olmo
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.
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. "
Palazzo Pacini
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
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."
Relais Villa Belvedere
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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.

Chianti Region Vacation Rental Travel Info

Vacation rentals
631
Popular accommodation
Chianti Region apartments
International airports
Florence (FLR-Peretola) and Pisa (PSA-Galileo Galilei)

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, (356)
"Très bien dans l’ensemble Bel ambiance. Très propre."
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
9.2 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."
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. "
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chianti Region vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chianti Region vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chianti Region in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as CNY282 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chianti Region rentals

At Expedia, we put the best Chianti Region vacation 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 vacation.

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.

Recent reviews of Chianti Region properties
Expedia 亿客行 verified reviews

Hotel Villa Cesi

Hotel Villa Cesi

5/5 Excellent
Wish we could stay longer
"A wonderful 2 night stay in Tuscany. This hotel is absolutely fabulous. Calm and relaxing place. The staff are so thoughtful and caring. The Manager / Owner should be so proud of all of them. Amazing"
A verified traveler stayed at Hotel Villa Cesi
Posted 2 days ago
Hotel Villa Cesi