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Check prices for these dates

Next weekend
31 Muh. - 2 Saf.
In two weeks
7 Saf. - 9 Saf.
In one month
21 Saf. - 23 Saf.
In two months
21 Rab. I - 23 Rab. I

Compare 1618 Villas in Gaiole in Chianti with updated reviews, rates, and availability.

Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Villa Simo, absolute tranquility

Villa with private pool on 25 acres in the heart of Chianti, close to Siena

9.8 out of 10, Exceptional, (67)
"The house is well equipped and perfect if you are looking for a quiet and out of the way house. Still a quick drive to Siena where everything can be found. would definitely recommend."
Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
Pool

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
Villa with pool and garden
Pool

Villa with pool and garden

Villa with pool and garden
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
Villa "Torre in Chianti" your homeaway in Tuscany!!!

Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.

10.0 out of 10, Exceptional, (106)
"The property was beautiful and just as advertised. Beatrice and Jacopo prepared several meals for us and the food was great and plentiful! They were wonderful hosts!"
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Exterior

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
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
Il Poggio dell'Eremita
Exterior

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (48)
"We received a warm welcome from the family and a thorough explanation of the facilities, the surrounding area and places of interest. Fabrizio communicated easily with us using the translation phone app. The apartment is very clean, well equipped and offers a genuine Italian experience. Simply wonderful."
The price is SAR 574
SAR 656 total
includes taxes & fees
24 Jan - 25 Jan
Il Poggio dell'Eremita
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Villa seen from the pool

FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI

10.0 out of 10, Exceptional, (56)
"Stay was excellent, a great house. Owners were super helpful. A property with over 100 olive trees. If I return this is where I will be 😎"
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Villa with private pool and panoramic view in beautiful Val d'Orcia
Pool

Villa with private pool and panoramic view in beautiful Val d'Orcia

10.0 out of 10, Exceptional, (5)
"We had stayed at this property for years before Jennifer purchased it. And do hope to continue. We appreciate the effort and care to details she put into updating it and providing an excellent experience. This property is well located to see numerous villages in the area."
Villa with private pool and panoramic view in beautiful Val d'Orcia
Luxury converted barn with hilltop views in chianti wine region, Tuscany
Sunset from our garden

Luxury converted barn with hilltop views in chianti wine region, Tuscany

10.0 out of 10, Exceptional, (87)
"I wish we could have stayed longer; such a beautiful location. The villa was very nice and comfortable. We enjoyed meals prepared by Serena twice during our visit; she cooked multi-course dinners that were delicious. Highly recommend the property and Serena’s cooking. We look forward to going back!"
Luxury converted barn with hilltop views in chianti wine region, Tuscany
Il Boschetto an oasis of peace and nature in Siena
Exterior

Il Boschetto an oasis of peace and nature in Siena

9.8 out of 10, Exceptional, (31)
"The location was excellent, 30 minute walk (2.1 km) to the main gate of Siena or 15 minute bus ride (bus stop 25 meters from the house). The home is beautiful, lots of amenities, it was very rustic. The pool area could use a good trimming, the online photos showed the property better than it actually was but not too far off."
Il Boschetto an oasis of peace and nature in Siena
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
Private pool

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
LA QUERCIA ESTATE, QUINTESSENTIAL ITALIAN EXPERIENCE

LA QUERCIA ESTATE, QUINTESSENTIAL ITALIAN EXPERIENCE

10.0 out of 10, Exceptional, (45)
"This is such a lovely property that I enjoyed with my family for a special birthday celebration. Our host Margherita is as beautiful as the property is magnificent. She was so gracious and helpful. We so enjoyed taking a cooking class with her and her mother Veronica, who learned traditional Tuscan cooking from her grandmother. They also made a delicious dinner for us one evening. The rooms are beautifully appointed in neutral shades and very comfortable. We highly recommend this fabulous...
LA QUERCIA ESTATE, QUINTESSENTIAL ITALIAN EXPERIENCE
Stunning private villa for 4 people with pool, WIFI, A/C, TV, terrace and parking
Water, Plant, Sky, Building, Swimming Pool, Azure, Tree, Shade, Outdoor Furniture, Grass

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

9.8 out of 10, Exceptional, (27)
"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 pool, WIFI, A/C, TV, terrace and parking
Gorgeous villa with pool and large garden private property amazing tuscan views
Pool

Gorgeous villa with pool and large garden private property amazing tuscan views

10.0 out of 10, Exceptional, (13)
"Best vacation EVER!!!! Our host was extremely attentive, helpful before and throughout our stay, We were greeted with fresh cherries from the property and a fruit basket. The property is very private, lovingly renovated and tastefully furnished. The pool is large and impeccably maintained. The home is located close to Arezzo and many sites worth visiting are close-by. The bed rooms are very comfortable and the house was spotless. We often enjoyed cooking and gathering in one of the multiple...
Gorgeous villa with pool and large garden private property amazing tuscan views
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

Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City
Villa MURGIANO's Infinity Edge Pool & spacious Lounging Area

Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City

9.8 out of 10, Exceptional, (98)
"This villa exceeded our expectations. It has ample room for a large family and was very neat and clean. The host was very attentive to all of our needs and very easy to communicate with. The location is just far enough away from Florence to give it a great Tuscan feel in the middle of a vineyard and olive orchard. I highly recommend this property. "
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City
Tailored to you・Villa w/heated pool and Concierge only 8 mile to Florence center
Outdoor dining

Tailored to you・Villa w/heated pool and Concierge only 8 mile to Florence center

10.0 out of 10, Exceptional, (96)
"We had a fantastic stay at this lovely villa. We were a group of two families with four adults and four kids ages 5 to 13. Cate, the hostess, was extremely attentive and helped us arrange various activities during our stay. She helped us arrange a cooking class at the villa, a bike tour through Chianti region with a private wine tasting, and a chef cooking a Thanksgiving meal for us (we opted for Tuscan - not American food). We also got to tour a working olive mill. In addition, upon hearing...
The price is SAR 3,592
SAR 4,115 total
includes taxes & fees
24 Jan - 25 Jan
Tailored to you・Villa w/heated pool and Concierge only 8 mile to Florence center
Luxury Villa in the Florentine hills
livingroom

Luxury Villa in the Florentine hills

9.8 out of 10, Exceptional, (133)
"Fantastic location near Florence. In driving distance to Florence yet it feels secluded and private. The view from the bedrooms and backyard is stunning. The house was in immaculate condition with all amenities for a wonderful stay. The host David was extremely responsive and professional. We highly recommend this property for anyone looking for a house with character in the countryside yet accessible to the main city centres."
Luxury Villa in the Florentine hills
Villa luna with pool and garden near the center of Siena
Outdoor dining

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
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
Pool

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
Pool

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
Restaurant

Hu Firenze Camping In Town

8.8 out of 10, Excellent, (1309)
"Nice experience overall!"
The price is SAR 196
SAR 243 total
includes taxes & fees
2 Feb - 3 Feb
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 574 and SAR 3,592 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 1618 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.