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Compare 1650 Villas in Gaiole in Chianti with updated reviews, rates, and availability.

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!!!
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
View from the dining room table

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

10.0 out of 10, Exceptional, (55)
"A+"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Luxury Villa in the Florentine hills
livingroom

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."
The price is AED 613
AED 858 total
includes taxes & fees
5 Jan - 6 January 2025
Luxury Villa in the Florentine hills
Villa Casa al Sole Large Private Pool, WiFi
Beautiful villa with private pool, terrace, and garden

Villa Casa al Sole Large Private Pool, WiFi

9.8 out of 10, Exceptional, (19)
"This is a beautiful villa with plenty of space for our large group. It is in a remote location and very quiet. It was perfect for short trips to local towns and then a swim in the afternoon. We spent most evenings on the patio enjoying the Tuscan sunsets. We would definitely stay again! "
Villa Casa al Sole Large Private Pool, WiFi
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
Beautiful private villa for 4 people with A/C, WIFI, pool, TV, terrace and parking
Water, Plant, Sky, Building, Swimming Pool, Azure, Tree, Shade, Outdoor Furniture, Grass

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

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 3,524
AED 4,041 total
includes taxes & fees
7 Jan - 8 January 2025
Tailored to you・Villa w/heated pool and Concierge only 8 mile to Florence center
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 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
Red House -- Country villa in Chianti Classico
Exterior

Red House -- Country villa in Chianti Classico

9.8 out of 10, Exceptional, (108)
"The little red house is a wonderful place to completely relax and enjoy the Tusan/Chianti countryside. Very secluded and quiet. Easy access to dining options. Our host, Stefano, was very helpful and replied quickly to any questions."
Red House -- Country villa in Chianti Classico
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.
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
View of the Villa from garden-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
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
San Gimignano - Panoramic garden and beautiful pool!
panoramic pool and garden

San Gimignano - Panoramic garden and beautiful pool!

9.8 out of 10, Exceptional, (36)
"This magnificent villa and the hosts, Cristina and Simone, surpassed our expectations and made a blissful stay in beautiful San Gimignano. The 300+ year old home was clean, charming and authentic and the grounds were well maintained and serene. The views of the countryside were breathtaking! At our request, the hosts arranged for a chef, Patrizia, to come to prepare dinner on 3 evenings. She was delightful and used fresh produce and ingredients from her own farm in the multi-course meals she...
San Gimignano - Panoramic garden and beautiful pool!
Villa Moriana by MMega
Exterior

Villa Moriana by MMega

Villa Moriana by MMega
Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.

Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.

10.0 out of 10, Exceptional, (9)
"This is a beautifully furnished and restored house. The quality of the furnishings and kitchens and bath are excellent. The pool is beautiful and we loved the covered loggia area so you could lounge poolside but still have cover from the sun. Easy to get to several interesting towns including Montalcino, Pienza, Montepulciano. The house manager was very helpful and pre-shopped for groceries and is available to line up lots of activities. Definitely recommend a stay with family or friends."
Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.
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
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
Elegant luxury villa near Florence with private pool and winery
Pool

Elegant luxury villa near Florence with private pool and winery

10.0 out of 10, Exceptional, (42)
"Heaven with daily service and smiles. Marco and staff were superb. Strongly recommend "
Elegant luxury villa near Florence with private pool and winery
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, (1291)
"Very clean and convenient (parking, supermarket, eatery, laundry, facilities for children, cooking in the chalet). The shuttle bus takes you to the main city centre in Florence where ponte vecchio and the plazas are located. "
The price is AED 284
AED 339 total
includes taxes & fees
24 Dec - 25 Dec
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 AED 613 and AED 3,524 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 1650 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.