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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 1504 Villas in San Casciano in Val di Pesa 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
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
Country House with heated pool near the center
Outdoor dining

Country House with heated pool near the center

9.8 out of 10, Exceptional, (8)
"These accomodations were wonderful! So convenient to take the tram to downtown! Host extremely responsive and helpfull."
The price is AED 1,009
AED 1,674 total
includes taxes & fees
12 Feb - 13 Feb
Country House with heated pool near the center
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
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
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 AED 3,521
AED 4,038 total
includes taxes & fees
23 Jan - 24 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
Beautiful Villa With Panoramic Views near San Gimignano
Collinella 14. A fully restored 3 bedroom, 2 bathroom semi detached house.

Beautiful Villa With Panoramic Views near San Gimignano

9.6 out of 10, Exceptional, (70)
"We had a wonderful stay and this property provided a nice central location from which to explore the region. Information from Steve was timely and extremely helpful. "
Beautiful Villa With Panoramic Views near San Gimignano
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
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
New 2 bed villa with large panoramic pool 40min to beaches
Pool

New 2 bed villa with large panoramic pool 40min to beaches

10.0 out of 10, Exceptional, (34)
"My wife and I had a fantastic week at the villa, we are very grateful to Mrs Consuelo for the hospitality and everything she did for us, what a fantastic lady!!! A great thank you to Mr Marcello for the free wine and fresh salad from the allotment, again thank you very much from Antonio & Louise from London"
New 2 bed villa with large panoramic pool 40min to beaches
Villa Moriana by MMega
Exterior

Villa Moriana by MMega

Villa Moriana by MMega
A Panoramic Tuscan Luxury - Villa Maria in Fronzano
The Villa

A Panoramic Tuscan Luxury - Villa Maria in Fronzano

10.0 out of 10, Exceptional, (70)
"This beautiful Tuscan estate exceeded expectations for our wine and culinary vacation! The view is spectacular. Our host, Tommaso, was extremely friendly and a gracious host. We brought in a chef for a Tuscan cooking class and the kitchen was well appointed. Parking the car was easy. Very modern bathrooms. Two wonderful rooms for group gathering areas inside. Highly recommend this property!"
A Panoramic Tuscan Luxury - Villa Maria in Fronzano
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 San Casciano in Val di Pesa

Hu Firenze Camping In Town
Restaurant

Hu Firenze Camping In Town

8.8 out of 10, Excellent, (1309)
"Nice experience overall!"
The price is AED 192
AED 238 total
includes taxes & fees
2 Feb - 3 Feb
Hu Firenze Camping In Town
Rivalta Hotel - Alfieri Collezione
View from property

Rivalta Hotel - Alfieri Collezione

4.0 star property
9.2 out of 10, Wonderful, (305)
"We stayed in a beautiful room with friendly staff. The location of the hotel was close to shopping and and many points of interest!"
The price is AED 373
AED 464 total
includes taxes & fees
26 Jan - 27 Jan
Rivalta Hotel - Alfieri Collezione
PopArtment
Lobby sitting area

PopArtment

9.0 out of 10, Wonderful, (691)
"Very nice place, not too far from train station but a further walk to most places. Not many places to eat around but we walked about 20 -30 mins and found something."
The price is AED 255
AED 323 total
includes taxes & fees
23 Jan - 24 Jan
PopArtment
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 San Casciano in Val di Pesa cost?
You can expect to pay between AED 1,009 and AED 3,521 per night for a villa in San Casciano in Val di Pesa. No matter your budget, an ideal stay is just a few clicks away 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 San Casciano in Val di Pesa?
Pick from 1504 villas in San Casciano in Val di Pesa. Whether you’re traveling with the family or organizing a weekend break with some friends, Expedia can help you find the right space for your crew.
Why book your villa in San Casciano in Val di Pesa with Expedia?
With Expedia, it’s easy to find your dream villa in San Casciano in Val di Pesa. Vacationing with the family? Use our filters to search for stays with amenities like free WiFi. If you have a budget, click on how much you’re willing to spend and the star rating of the property. We’ll help you find the perfect pad that suits your style and taste.
How can I find cheap villas in San Casciano in Val di Pesa?
With Expedia’s filter tool, scoring cheap villas in San Casciano in Val di Pesa has never been easier. To find stays that won’t break the bank, refine your search results by star rating, budget and amenities.