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Search Villas in San Casciano in Val di Pesa

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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 1939 Villas in San Casciano in Val di Pesa with updated reviews, rates, and availability.

Your panoramic house in Tuscany between vineyards and olive groves.
Exterior

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (36)
"We had such a nice stay and only wish it had been longer! Enrico & Simona were excellent hosts and we loved the cooking class they did for us and our 3 college students who learned to make pasta for the first time. The views are spectacular and it’s a perfect location for trips to the many surrounding towns and wineries. We’d love to come back in the summer and stay longer!"
Your panoramic house in Tuscany between vineyards and olive groves.
Beautiful villa with WIFI, private pool, TV, panoramic view and parking, close to Florence
Pool

Beautiful villa with WIFI, private pool, TV, panoramic view and parking, close to Florence

Beautiful villa with WIFI, private pool, TV, panoramic view and parking, close to Florence
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
Outdoor pool

Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa

10.0 out of 10, Exceptional, (39)
"The villa is quiet and so picturesque. The views are incredible. The accommodations comfortable and the outdoor space absolutely amazing!"
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
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
Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence
Exterior

Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence

9.6 out of 10, Exceptional, (46)
"We had a great stay here. All of us really enjoyed the location!"
Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence
Elegante villa con piscina a soli 12 km da Firenze ideale per famiglie e gruppi
Pool

Elegante villa con piscina a soli 12 km da Firenze ideale per famiglie e gruppi

Elegante villa con piscina a soli 12 km da Firenze ideale per famiglie e gruppi
Relaxation in the green, in the municipality of Monteriggioni just 7 km from Siena
Outdoor pool

Relaxation in the green, in the municipality of Monteriggioni just 7 km from Siena

Relaxation in the green, in the municipality of Monteriggioni just 7 km from Siena
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
Outdoor pool, sun loungers

Villa "Le Vallecchie" overlooking Siena and with private swimming pool

9.6 out of 10, Exceptional, (30)
"Really enjoyed our stay. A great place to relax."
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Terrace/patio

15th century barn fully renovated in a stylish style with gorgeous swimming pool

9.2 out of 10, Wonderful, (7)
"Only regret is that we couldn’t stay longer to explore more of Tuscany. Wish weather was a bit warmer to use the beautiful pool. Overall beautiful home with upscale features! We really enjoyed our stay!"
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
Outdoor 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
LUXURY VILLA WITH PRIVATE POOL
Fridge, microwave, oven, stovetop

LUXURY VILLA WITH PRIVATE POOL

10.0 out of 10, Exceptional, (7)
"Everything was even better than expected. Plumbing issues did arise and should be addressed. We loved our stay and would recommend it highly to others"
LUXURY VILLA WITH PRIVATE POOL
Holiday home in the Florentine Chianti half an hour from Florence
Interior

Holiday home in the Florentine Chianti half an hour from Florence

9.8 out of 10, Exceptional, (55)
"This house was perfect for our group of 9 girlfriends. Every room had a bathroom to share which was so convenient. It’s location was also perfect to explore Tuscany and all the hysterical gems. Montespertoli is a beautiful town to visit and Bruno was an excellent host! "
Holiday home in the Florentine Chianti half an hour from Florence
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City
Outdoor pool

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

9.8 out of 10, Exceptional, (100)
"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
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Outdoor pool

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

10.0 out of 10, Exceptional, (53)
"Gabbianuzzo was so beautiful and secluded. We had a wonderful time exploring Tuscany from this villa. "
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Villa Le Balze Large Private Pool, WiFi
View from property

Villa Le Balze Large Private Pool, WiFi

9.8 out of 10, Exceptional, (17)
"An excellent choice for a worry-free and comfortable stay."
Villa Le Balze Large Private Pool, WiFi
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Outdoor pool

BEAUTIFUL VILLA with private Pool in the heart of Chianti

10.0 out of 10, Exceptional, (21)
"We were a group of 4 families with toddlers and loved our stay at the villa! Alessandro was an excellent host and very responsive. The views and pool are stunning, and the house is clean and decently equipped. Highly recommended for a group stay in Chianti!"
BEAUTIFUL VILLA with private Pool in the heart of Chianti
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (59)
"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
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Outdoor 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
Villa Andrei, a relaxing bath in the Tuscan countryside with private pool
Property grounds

Villa Andrei, a relaxing bath in the Tuscan countryside with private pool

10.0 out of 10, Exceptional, (53)
"The landscape around is amazing and the house is very welcoming. We spent a very nice week overthere."
Villa Andrei, a relaxing bath in the Tuscan countryside with private pool
Private villa in the heart of chianti with view of siena
Pool

Private villa in the heart of chianti with view of siena

Private villa in the heart of chianti with view 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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Frequently asked questions

How much do villas in San Casciano in Val di Pesa cost?
Rates for villas in San Casciano in Val di Pesa range between and per night. Whatever your budget, you can find a place that suits your needs with 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?
You’ll find 1939 villas in San Casciano in Val di Pesa. No matter if you’re traveling with the kids or organizing a weekend break with your besties, Expedia can help you find the ideal base for your squad.
Why book your villa in San Casciano in Val di Pesa with Expedia?
Reserving a villa in San Casciano in Val di Pesa is as easy as working out your travel dates and choosing a place that checks your boxes. In search of something affordable or luxurious, or a stay that also offers a kitchenette? Use Expedia’s search filters to narrow your results and find the ideal fit.