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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare 1662 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
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.
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
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
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
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 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 AED 567
AED 647 total
includes taxes & fees
17 Feb - 18 Feb
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
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
Wonderful 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

Wonderful private villa for 4 people with pool, WIFI, 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 pool, WIFI, A/C, 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

Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the
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 AED 3,661
AED 4,197 total
includes taxes & fees
19 Feb - 20 Feb
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."
The price is AED 617
AED 1,033 total
includes taxes & fees
17 Feb - 18 Feb
Luxury Villa in the Florentine hills
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
Apartment Suite Azalea. Pool, panoramic view on the Chianti hills.
Pool

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 IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
Pool

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.

10.0 out of 10, Exceptional, (113)
"From the first contact until our checkout, the communication was excellent. The Villa was very well decorated and provided an excellent venue for our 12 person group. The chef and hostess prepared a delicious meal and extraordinary service. The Villa provided an excellent place to rest for our group. Everyone had their own bedroom and bathroom. Caterina, Gabriel and Carolina were EXCELLENT to work with! I would definitely recommend this Villa to anyone looking for a central location in...
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
Villa in Montalcino, exclusive for you, stunning view!!!
Exterior

Villa in Montalcino, exclusive for you, stunning view!!!

10.0 out of 10, Exceptional, (78)
"We absolutely loved our stay at this villa! It was just wonderful, and Luigi was a fantastic host! The views from every part of the villa are amazing! It was so fun to see all of the sheep each morning and watch the sunset in the evenings. We were fortunate enough to be in town for the olive festival in Montisi, the quaint little village just a few miles away. We had a blast! The recommended chef who cooked for us at the villa, Giancarlo from the Tuscan Chef, was incredible! What a fantastic...
Villa in Montalcino, exclusive for you, stunning view!!!
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

Chianti Holiday House, private jacuzzi up to 6 pax
Jacuzzi in the garden

Chianti Holiday House, private jacuzzi up to 6 pax

9.4 out of 10, Exceptional, (19)
"• Pros: Beautiful grounds, garden and hot tub; dishwasher was greatly appreciated, lovely views, excellent Instructions to reach the village. Cons: • Internet/cell connectivity in village is poor and upon arrival, couldn’t connect with cell phone OR my portable wifi. I couldn’t reach the owners, and had no photos to identify the house was ours, and instructions were incomplete. Had to knock on doors which was awkward. • Password for the wifi is wrong. Passwords are case-sensitive! This wasted a...
Chianti Holiday House, private jacuzzi up to 6 pax
Hu Firenze Camping In Town
Restaurant

Hu Firenze Camping In Town

8.8 out of 10, Excellent, (1320)
"We stayed in a 2 bedroom, 2 bath unit with a small kitchenette. There was a laundramat on site which was great. It us conveniently located if you have a car. The kitchenette had a small refrigerator, a mucrowave, and a cooktop. No oven. "
Hu Firenze Camping In Town
Il Battistero Siena - Residenza d'Epoca
Room

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (150)
"Wonderful location!!! Everything within walking distance. Friendly staff, clean modern room. Shower needs repairing. Will definitely return to stay here. If you are driving to the hotel, It’s a ZTL zone so contact the hotel to make arrangements for your car to be garaged. Don’t need a car here. It is in the best location!!!"
The price is AED 527
AED 595 total
includes taxes & fees
17 Feb - 18 Feb
Il Battistero Siena - Residenza d'Epoca
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 AED 567 and AED 3,661 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 1662 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.