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Compare 1694 Villas in Gaiole in Chianti with updated reviews, rates, and availability.

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
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
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
10.0 out of 10, Exceptional, (93)
"We had the most amazing stay at this beautiful villa. Everything about it was picturesque and relaxing. This villa has all of the modern amenities but still exudes Tuscan charm. Pre- visit communication was smooth and very prompt. The highlight of the stay was the dinner cooked for us the first night by Chef Vanna and Francesca. I am not exaggerating when I say it was by far the best meal we had during our trip to Tuscany and we ate at many very nice restaurants. If you are booking a stay I...
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
10.0 out of 10, Exceptional, (104)
"we had an amazing week at this villa with 18 family members, age 6 months to 87 years. Jacobo and Beatrice were so nice , very welcoming and super helpful with transportation and amenities nearby. If we had any problems we could easily text and Jacopo would immediately answer . i would recommend coming here ! Faboulous"
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
Mansion - Arezzo
9.0 out of 10, Wonderful, (22)
"Stayed here for 14 days. Generous space with lots of room for multiple guests. We didn't realize the villa was two separate units. This was unexpected as we thought there would be a central indoor staircase. We made it work but we did feel separate from each other. Eduardo brought us lovely treats from a local bakery a couple of times which was very kind. You definitely need a vehicle to stay here. While it says there are a few things in walking distance we felt the car was necessary....
Mansion - Arezzo
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
10.0 out of 10, Exceptional, (45)
"Luigi went above and beyond in providing suggestions of restaurants and things to do in the area. He was also helpful when we were have trouble calling our car rental….always willing to help out and answer questions. The home is very clean and has the old Italian rustic charm. The beds were comfortable. There is no AC but fans are provided for every room. There were beautiful sunsets every night by the pool. The views of the rolling Tuscan hills were spectacular. The color and intensity of the...
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
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.
10.0 out of 10, Exceptional, (41)
"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
10.0 out of 10, Exceptional, (19)
"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
Stunning private villa for 4 people with WIFI, A/C, pool, 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...
Stunning private villa for 4 people with WIFI, A/C, pool, TV, terrace and parking
Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the
Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the
Luxury Villa in the Florentine hills
9.8 out of 10, Exceptional, (129)
"My husband and I stayed a month here. While access is kind of a challenge (need a car and the roads are narrow) the location is beautiful and very quiet. We decided it was a nice change from the crowds and noise of Florence and other tourist spots at the end of the day. The villa itself is exactly as portrayed in the pictures. Big, clean, well equipped for any stay. We found the best way to get into Florence was to drive into Grassina, park and take the local buses. Great access and saved a...
Luxury Villa in the Florentine hills
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
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
Luxury villa just 14 km from Florence. Sleeps 16 with hydromassage, sauna & gym!
10.0 out of 10, Exceptional, (31)
"The villa was very nice, but the path to get to the villa is very poorly maintained. Also, during our stay the roof leaked into one of the bedrooms and the heating system was not set up for cold weather yet.."
Luxury villa just 14 km from Florence. Sleeps 16 with hydromassage, sauna & gym!
Your panoramic house in Tuscany between vineyards and olive groves.
9.8 out of 10, Exceptional, (31)
"Enrico and Simona have a special place in an incredible area. The views are amazing and all of the little towns are historic and have great little restaurants. The Villa is well equipped and very comfortable. The hosts are kind and full of helpful info on the area. Make sure to take a guided tour of the Benedictine Monastery nearby. Couldn’t have a better stay in Tuscany."
Your panoramic house in Tuscany between vineyards and olive groves.
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 SAR 448
SAR 537 total
includes taxes & fees
16 Nov - 17 Nov
Double room with private parking within walking distance of downtown!
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
10.0 out of 10, Exceptional, (46)
"This place exceeded all of our expectations. The host and his family were amazing and very accommodated. Perfect size for two couples. Bedrooms and bathrooms were private. The location was perfect. We were able to take daily trips everywhere in Tuscany between 15 minutes and one hour. The house and pool were even better than the pictures portray. The place came stocked with everything you need For your vacation. If ever back in Tuscany I would definitely stay here again."
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
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
Charming Villa with private pool <br>Villaventotto
9.8 out of 10, Exceptional, (16)
"We had a great time. We stayed for two days"
The price is SAR 1,343
SAR 2,079 total
includes taxes & fees
1 Dec - 2 Dec
Charming Villa with private pool <br>Villaventotto
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 Gaiole in Chianti

Farmhouse apartment in Chianti with garden and pool for 2 people
9.4 out of 10, Exceptional, (36)
"Wonderful hosts, quiet ancient setting Highly recommend"
Farmhouse apartment in Chianti with garden and pool for 2 people
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
8.8 out of 10, Excellent, (3)
"Property is off the beaten track so very peaceful. La Luna was a little small in the kitchen lounge area for 4 people (needs another sofa). Unfortunately we had a few issues that we told the manager about at the end of our stay in the hope that they will be sorted for future visitors. We couldn’t get the tv to work (only wanted to watch Euro football finals!), dishwasher wouldn’t work and the plug sockets were a nightmare with a need for a lot more adapters or extension leads that would fit the...
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
Hu Firenze Camping In Town
8.8 out of 10, Excellent, (1269)
"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 SAR 222
SAR 269 total
includes taxes & fees
11 Nov - 12 Nov
Hu Firenze Camping In Town
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 Gaiole in Chianti cost?
Villas in Gaiole in Chianti cost between SAR 448 and SAR 1,343 per night. These stays give you the privacy to enjoy your own space at a price you can afford. 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 Gaiole in Chianti?
You can choose from 1694 villas in Gaiole in Chianti. No matter if you’re traveling with the family or organizing a weekend escape with some friends, Expedia can help you find the right space for your whole crew.
Why book your villa in Gaiole in Chianti with Expedia?
We think that vacations shouldn’t be complicated, so if you’re in search of villas at an affordable rate, Expedia has your back. Save those pennies and select an all-inclusive stay, or splurge on a high-end villa to treat your sweetheart. Use our handy search filters to find a property in Gaiole in Chianti that suits you best.
How can I find cheap villas in Gaiole in Chianti?
A wonderful way to zero in on cheap villas in Gaiole in Chianti is with Expedia’s convenient filter tool. Refine your search results by amenities, star rating and budget to grab unbeatable bargains in only a couple of clicks.