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Featured Villas in Radda in Chianti and around

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Outdoor pool
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
10.0 out of 10, Exceptional, (95)
"Our host was responsive to our questions and needs. He also arranged a women to come to the property and prepare dinner for us on two separate nights.To our host, thank you."
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Outdoor pool
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
10.0 out of 10, Exceptional, (84)
"Alessandro was a fantastic host! He always made us feel right at home. Addressing all of our questions regarding the local area. The property was exactly what we expected. The surrounding area was magnificent. "
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Private villa near Certaldo and San Gimignano with swimming pool and large garden.
Outdoor dining
Private villa near Certaldo and San Gimignano with swimming pool and large garden.
9.4 out of 10, Exceptional, (28)
"The location of the villa is fantastic and the villa itself is extremely well laid out, clean and comfortable. We loved our stay and the host was incredibly helpful and friendly. We would be happy to stay again, our one suggestion would be that perhaps some of the finishings could be updated, they were obviously very trendy and cutting edge when designed, but perhaps could be improved by some modernisation, and I think the villa would then be perfect."
Private villa near Certaldo and San Gimignano with swimming pool and large garden.
Villa in Toscana - Reggello con Piscina, Wi-Fi, Giardini.
Outdoor pool
Villa in Toscana - Reggello con Piscina, Wi-Fi, Giardini.
10.0 out of 10, Exceptional, (42)
"Had a great two week vacation at Eduardo's place in Reggello. Beautiful little cabin with a pool and well kept yard, set within an olive orchard and vineyard. Hosts passed along some fresh eggs from the hens and tomatoes from the property. The house seems quite new by Italian standards and is in excellent condition. Pool is fantastic. We had a great stay and would highly recommend this spot for small groups and families. "
Villa in Toscana - Reggello con Piscina, Wi-Fi, Giardini.
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Outdoor pool
BEAUTIFUL VILLA with private Pool in the heart of Chianti
10.0 out of 10, Exceptional, (20)
"We rented the villa after a family event. The owners and their son are very charming and accommodating. We enjoyed the villa as it is very authentic. Felt like we were locals. It has separate areas almost like apartments within the villa which is great if you have many couples. One of the rooms has bunk beds and the other two twin beds. It’s important to know you can’t walk anywhere so a car is needed. That’s the only reason for my location rating. Excellent villa to spend time with friends and...
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Wonderful private villa for 4 people with WIFI, pool, A/C, TV, terrace and parking
Pool
Wonderful private villa for 4 people with WIFI, pool, A/C, TV, terrace and parking
9.8 out of 10, Exceptional, (28)
"Nice house suitable for a family of 3-4. Two bed rooms, one with a double bed. Living room and well equipped kitchen. Very cozy property a kilometer or so from the town center. The host family lives in another house on the same property, and are very nice and hospitable, while not being intruding in any way. The private church on the property is worth a visit, it was built in 710 a.d. and has frescos from the 1500s inside. The pool is very nice, and there is a nice playground for children. We...
Wonderful private villa for 4 people with WIFI, pool, A/C, TV, terrace and parking
Luxury Villa in the Florentine hills
Fridge, microwave, oven, stovetop
Luxury Villa in the Florentine hills
9.8 out of 10, Exceptional, (130)
"We loved our stay. From the start David sent all kinds of information. We had a few more questions about the bus and the area, David sent answers with in minutes with GPS maps. We loved the view, the Persimmon and Pomegranate from the trees in the yard were delicious. All of the bedrooms and bathrooms were awesome, everything was clean. We stayed at 3 other locations this trip and this was our favorite. My wife said the blow dryer was the best blow dryer in Italy."
Luxury Villa in the Florentine hills
Villa luna with pool and garden near the center of Siena
Fridge, microwave, oven, dishwasher
Villa luna with pool and garden near the center of Siena
9.0 out of 10, Wonderful, (27)
"The home had everything we needed. The view from the villa was truly picturesque. A+++++!"
Villa luna with pool and garden near the center of Siena
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Outdoor pool
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
9.6 out of 10, Exceptional, (53)
"The property was beautiful and very safe. The pool was fabulous , the scenery breath taking and the hosts very friendly and welcoming people. Close to hiking trails with a pizzeria close by . A car is recommended with parking in a gated property . "
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Authentic country house originally a convent, dates back to around the year 1000
Outdoor dining
Authentic country house originally a convent, dates back to around the year 1000
9.6 out of 10, Exceptional, (50)
"Beautiful place and a very friendly and helpful host. Authentic Tuscan farmhouse with no frills. Lovely views all round, especially from the terrace. Excellent bar/ restaurant within walking distance. It was very hot when we were there, so the location of the pool across the road was a problem. Otherwise,great."
Authentic country house originally a convent, dates back to around the year 1000
Luxury villa just 14 km from Florence. Sleeps 16 with hydromassage, sauna & gym!
Outdoor dining
Luxury villa just 14 km from Florence. Sleeps 16 with hydromassage, sauna & gym!
10.0 out of 10, Exceptional, (32)
"Villa Il Forte is the most incredible setting. It is an incredible historic and luxurious home while being comfortable, spacious and accommodating. Many different spaces to relax, connect and play. Paolo’s team were absolutely amazing. The chef Thomas is so talented while also being wonderfully personable and fun. The driver Fabrizio was so generous and thoughtful. His guides were knowledgeable and friendly. I have already booked it for next year! I can’t wait to go back! "
Luxury villa just 14 km from Florence. Sleeps 16 with hydromassage, sauna & gym!
Your panoramic house in Tuscany between vineyards and olive groves.
Exterior
Your panoramic house in Tuscany between vineyards and olive groves.
9.8 out of 10, Exceptional, (33)
"Simona and Enrico were at the house to great us and also have a new washer installed. The home is everything we hoped for- clean, a well stocked kitchen, large upstairs bathroom and breathtaking views. It was the perfect place for us to unwind after several days in hotels. The home has several information brochures for wine tasting and restaurants.. Simon’s and Enrico were the perfect hosts. Highly recommend their home. "
Your panoramic house in Tuscany between vineyards and olive groves.
Double room with private parking within walking distance of downtown!
Property grounds
Double room with private parking within walking distance of downtown!
7.6 out of 10, Good, (5)
"Easy Walking to all there is to see in Siena!!! Car is parked safely in front of villa no extra charge. Quiet Apartment is in the basement bathroom is upstairs. Monica is very welcoming and informative. "
The price is €136
includes taxes & fees
28 Nov - 29 Nov
Double room with private parking within walking distance of downtown!
Villa with private swimming pool in quiet area, private garden, panoramic views
Outdoor pool, pool loungers
Villa with private swimming pool in quiet area, private garden, panoramic views
10.0 out of 10, Exceptional, (8)
"La maison est très calme, très propre et bien équipée, accessible en partie par un chemin de terre depuis le joli village de Radicondoli, . La vue sur les collines avoisinantes est très agréable, en particulier de la piscine (hors-sol). Il faut compter environ 45 minutes de jolies routes pour se rendre à Sienne, Volterra ou San Giminiano. Beaucoup d'animaux sauvages dans la nature, si vous êtes chanceux comme nous... Sarka est une hôtesse sympathique et attentionnée. Avec son mari, elle produit...
Villa with private swimming pool in quiet area, private garden, panoramic views
Luxury Villa with large pool close to Florence
Outdoor pool
Luxury Villa with large pool close to Florence
10.0 out of 10, Exceptional, (62)
"Beautiful, historic villa with a fantastic view of the valley below. Our hosts were friendly, helpful and entertaining as well. The icing on the cake was Fonsi's providing breakfast and cooking dinners as requested. Her chef skills were more than we could ask for. "
Luxury Villa with large pool close to Florence
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
Exterior
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
9.8 out of 10, Exceptional, (9)
"The villa is beautiful, spacious, clean and comfortable. The location is excellent. There are horses and ponies on the grounds. The best part is the hostess and the host. They are so accomadating and kind. The pasta we dinner and pizza party were great! "
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
View from property
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
9.6 out of 10, Exceptional, (17)
"Our 2-wk. reservation (Oct. 5-19) was actually increased by a week Sept. 28-Oct. 5, making it a 3-wk reservation, however, due to a medical issue, we had to return to the USA 10 days early. Gabriella was a wonderful property manager assisting us with seeking medical and hospital care. Lovely property and location."
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
Villa with private swimming pool on the Florentine hills 25 Km from Florence
Outdoor pool
Villa with private swimming pool on the Florentine hills 25 Km from Florence
10.0 out of 10, Exceptional, (44)
"What a slice of paradise Marco's house is, it is better than the photos and the perfect place to retreat to after exploring the Tuscan countryside. Mrs Lucia, her sister and daughter gave us an unforgettable evening teaching us how to make pasta...something the kids will never forget. The pool was a beautiful relief from the heat. Beds very comfortable. Marco a great communicator. We would definitely come back stay!"
Villa with private swimming pool on the Florentine hills 25 Km from Florence
Molino del Ponte, Radda in Chianti, Italy
Exterior
Molino del Ponte, Radda in Chianti, Italy
9.6 out of 10, Exceptional, (5)
"En un mot.. parfait "
Molino del Ponte, Radda in Chianti, Italy
VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.
Outdoor pool, pool loungers
VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.
10.0 out of 10, Exceptional, (7)
"The house was great and Paula and Niccolo the best. Not a lot of restaurants nearby and you need to make reservations, but about 15 minuntes to Florence."
VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.
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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Other property types in Radda in Chianti

Hu Firenze Camping In Town
Seasonal outdoor pool
Hu Firenze Camping In Town
8.8 out of 10, Excellent, (1280)
"Overall our stay in Hu Firenze was great. The restaurant on location was really cool and tasted pretty great too. The staff was friendly and helpful. Our little house was a big tent basically. Interesting but annoying when people would come check it out or tap on our house (happened a couple times). It was kinda funny but always awkward. We had a bed, closet, mini fridge, and bathroom. They had a shuttle to take you partially into town or you could walk to Firenze Rovezzano (train station)....
The price is €63
includes taxes & fees
27 Nov - 28 Nov
Hu Firenze Camping In Town
PopArtment
Bicycling
PopArtment
9.0 out of 10, Wonderful, (683)
"Great place for families."
The price is €100
includes taxes & fees
2 Dec - 3 Dec
PopArtment
Forte16
Terrace/patio
Forte16
9.6 out of 10, Exceptional, (756)
"Clean and modern accounting accommodations "
The price is €125
includes taxes & fees
25 Nov - 26 Nov
Forte16
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.

Frequently asked questions

How much do villas in Radda in Chianti cost?
Rates for villas in Radda in Chianti range between €136 and €136 per night. Whatever your budget, you’re sure to find a place that suits 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?
Lock in your holiday dates and then choose from 1493 villas in Radda in Chianti. For a family adventure, a getaway with your besties and everything in between, Expedia will help you find the ideal space in just a few clicks.
Why book your villa in Radda in Chianti with Expedia?
Expedia makes it easy to find your ideal villa in Radda in Chianti. Taking the kids on holiday? Make use of our filters to look for stays with amenities like WiFi and a pool. If you’re on a budget, decide on how much you’d like to spend and your preferred star rating. We’ll help you find a perfect place that suits your style and taste.
How can I find cheap villas in Radda in Chianti?
The best way to locate cheap villas in Radda in Chianti is with Expedia’s handy filter tool. Fine-tune your search results by star rating, amenities and budget to grab awesome bargains in only a few keystrokes.
What is there to do near my villa in Radda in Chianti?
If you want to fill up your itinerary in Radda in Chianti, make your way to Castello di Albola. It’s a favourite among locals and tourists alike.