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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Villas in Radda in Chianti and around

Relais Badia a Passignano
Land view from property

Relais Badia a Passignano

10.0 out of 10, Exceptional, (1)
Relais Badia a Passignano
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Relax in a serene outdoor space with a lush landscape view, a pool, and comfortable seating.

Villa in Poggiarello-ripa with 3 bedrooms sleeps 5

10.0 out of 10, Exceptional, (110)
"We had a large group of family and friends comfortably stay here. The host was very available and helpful, and personally showed us around the property upon our arrival. The property description is accurate. "
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Villa with pool and garden
Enjoy a serene outdoor space with a stone wall, arched window, and scenic views of the surrounding mountains.

Villa with pool and garden

Villa with pool and garden
Made for gathering together, leave the rest to us - Villa 20 minutes to Florence
Stunning stone building with a large arched doorway and windows, set amidst a charming entrance.

Made for gathering together, leave the rest to us - Villa 20 minutes to Florence

10.0 out of 10, Exceptional, (102)
"The villa is absolutely stunning & our stay was an amazing experience. We had a small wedding ceremony with our guests followed by a home cooked Italian dinner which was the most perfect evening. Cate & her family were very accommodating and made us feel very welcome. Cate made our stay stress-free and was more than happy to help organise anything we may have needed for our stay. I can’t wait to stay again "
The price is €1,624
includes taxes & fees
1 Sept - 2 Sept
Made for gathering together, leave the rest to us - Villa 20 minutes to Florence
Villa Costa, Stunning Villa in the heart of Tuscany.
Situated in a rural countryside setting, this charming home features a traditional stone building with a sloped roof.

Villa Costa, Stunning Villa in the heart of Tuscany.

10.0 out of 10, Exceptional, (36)
"You have all the amenities of a large, historic villa - and also the real farmland all around you. Sheep, horses, dogs - beautiful, and not in your personal space (unless you want them to be!). Pasqualina and her son Francesco are perfect hosts. Incredibly responsive, even with a language barrier. If I return to Tuscany I would want to stay here again. Thank you so much."
Villa Costa, Stunning Villa in the heart of Tuscany.
Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool
Enjoy dining or socializing in the covered outdoor seating area surrounded by a serene garden.

Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool

10.0 out of 10, Exceptional, (53)
"We really appreciate the place and the quieteness of the house. The house is very beautiful and well equipped. We have spent a great week in Torre di Pancole. "
Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool
Stunning Villa: 24 guests, private SwimmingPool
Experience the serene atmosphere of our traditional garden, surrounded by a variety of plants and a small pond.

Stunning Villa: 24 guests, private SwimmingPool

9.8 out of 10, Exceptional, (28)
"We had a fantastic time at the house, Fabio was excellent in his communication and help. The house is great with separate areas but big communal spaces. We had a couple of delicious meals cooked for us by Fabio, I would highly recommend this luxury! If I had to say one thing it would be great if the pool seating area was tiled instead of grass, but overall can't fault it."
Stunning Villa: 24 guests, private SwimmingPool
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
Relax by the serene pool surrounded by lush greenery and olive trees.

Villa Salivolpe - on top of a Chianti hill - Private swimming pool

9.6 out of 10, Exceptional, (22)
"The villa was a beautiful home to send our our time in Tuscany, Italy. We enjoyed having our own bedrooms and baths. We had a special meal cooked by a local chef, Rachel. The kitchen worked well for the cooking, and for our breakfasts. The scenery was just breathtaking, and it is just as pictures in books looked like. We very much enjoyed our stay."
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Relax in style on the patio, surrounded by lush views and a refreshing pool.

15th century barn fully renovated in a stylish style with gorgeous swimming pool

9.2 out of 10, Wonderful, (10)
"We were two couples looking for an authentic Tuscan experience in the gorgeous countryside. The location is well suited to travel to Montalpucino, Chianti, San Gimignano, Volterra, Pisa and Florence. Both Mido and David were very attentive towards making our visit comfortable . A gorgeous building with high quality style and finishes. A top contender for best vrbo property I have ever visited. Thank you!"
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Luxury Villa Basilio Chianti
Seasonal outdoor pool

Luxury Villa Basilio Chianti

Luxury Villa Basilio Chianti
Stunning private villa for 4 people with pool, WIFI, A/C, TV, terrace and parking
Guests can enjoy a porch surrounded by lush gardens and a well-manicured lawn.

Stunning private villa for 4 people with pool, WIFI, A/C, TV, terrace and parking

9.8 out of 10, Exceptional, (29)
"Mooie woning met een grote tuin en fijn zwembad. [English translation courtesy of Easy Reserve] Beautiful home with a large garden and lovely pool."
Stunning private villa for 4 people with pool, WIFI, A/C, TV, terrace and parking
Your panoramic house in Tuscany between vineyards and olive groves.
Surrounded by lush greenery and vineyards, this house offers a tranquil environment.

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (39)
"We had such a nice stay and only wish it had been longer! Enrico & Simona were excellent hosts and we loved the cooking class they did for us and our 3 college students who learned to make pasta for the first time. The views are spectacular and it’s a perfect location for trips to the many surrounding towns and wineries. We’d love to come back in the summer and stay longer!"
Your panoramic house in Tuscany between vineyards and olive groves.
Private villa in the heart of chianti with view of siena
Relax by the serene pool surrounded by lounge chairs and tables under a large tree.

Private villa in the heart of chianti with view of siena

10.0 out of 10, Exceptional, (1)
"Fantastiskt boende med underbar trädgård och utsikt, nära vingårdar och historiska städer!"
Private villa in the heart of chianti with view of siena
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Standalone residence with a traditional Mediterranean architectural style, surrounded by lush greenery.

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

10.0 out of 10, Exceptional, (53)
"The house was fantastic and had more than enough space for our large family. What was particularly great was the large table where we always ate before we went to the very large swimming pool."
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Villa Franchetti - Luxurious Florentine Villa with Swimming Pool
Stately building with a classical facade, featuring a central entrance and manicured gardens.

Villa Franchetti - Luxurious Florentine Villa with Swimming Pool

10.0 out of 10, Exceptional, (15)
"We enjoyed this beautiful property It was just like in the pictures!!! Everything worked perfect"
Villa Franchetti - Luxurious Florentine Villa with Swimming Pool
Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence
Set amidst lush greenery and olive groves, this property offers a serene outdoor space with a swimming pool and sun terrace.

Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence

9.6 out of 10, Exceptional, (48)
"We had a great stay here. All of us really enjoyed the location!"
Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence
Beautiful Villa With Panoramic Views near San Gimignano
Relax by the serene pool surrounded by lush greenery and distant hills.

Beautiful Villa With Panoramic Views near San Gimignano

9.6 out of 10, Exceptional, (73)
"Nice area! We enjoyed the terasse and the pool a lot "
Beautiful Villa With Panoramic Views near San Gimignano
Villa Casa al Sole Large Private Pool, WiFi
Relax by the serene pool surrounded by lush greenery and trees.

Villa Casa al Sole Large Private Pool, WiFi

9.8 out of 10, Exceptional, (20)
"Thank you for a fantastic experience - everything was just right."
Villa Casa al Sole Large Private Pool, WiFi
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Relax by the pool with comfortable lounge chairs and a wicker basket for your essentials.

4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC

8.0 out of 10, Very good, (1)
"We spent a great family time at Adme’s house.The house has everything. Was very clean and well maintained . Will highly recommend."
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Villa with unique view of Siena with private pool
Stroll through the beautifully maintained garden, featuring a variety of flowering plants and a charming, rustic building with an arched doorway.

Villa with unique view of Siena with private pool

10.0 out of 10, Exceptional, (6)
"I booked Letizia's amazing Villa for a week-long birthday celebration and we loved every minute of our time in the Tuscan sun! It was great to be able to relax by the pool in the peace of the countryside amongst the olive groves while still being only a short walk away from Siena, we just wish we could have stayed for longer!"
Villa with unique view of Siena with private pool
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.
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Top Radda in Chianti Hotel Reviews

IQ Hotel Firenze

IQ Hotel Firenze

10/10 Excellent
"Great Hotel and I will come again "
Rodney 2-night trip
Posted 1 day ago
IQ Hotel Firenze

Frequently asked questions

How much do villas in Radda in Chianti cost?
Rates for villas in Radda in Chianti range between €1,624 and €1,624 per night. No matter your budget, you're sure to find a place that fits your needs on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Radda in Chianti?
Radda in Chianti has 1929 villas to select from. Find a place that's right for you quickly and easily by checking the "Villa" box under the "Property type" tab in our handy filter tool.
Why book your villa in Radda in Chianti with Expedia?
Reserving a villa in Radda in Chianti is as simple as clicking on your travel dates and picking a place that meets your needs. Seeking something affordable or upmarket, or a stay that also features WiFi and a hot tub? Use Expedia's search filters to narrow your results and find your dream fit.