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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for San Casciano in Val di Pesa villas

Exterior

Villa in Florence

Beautiful Tuscan home between Florence & Siena
10.0 out of 10, Exceptional, (7 reviews)
"Judy was amazing and very helpfulNothing to do with the property, but I sure you pre book all nights out/transportation"
United States
Frank V.
The price is ￥119,330
￥220,429 total
includes taxes & fees
Jan 25 - Jan 26
Beautiful Tuscan home between Florence & Siena
Exterior

Villa in Careggi Rifredi

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
10.0 out of 10, Exceptional, (1 review)
"Staff went over and above for us. Food was wonderful service 5 stars"
United States
robert g.
The price is ￥1,753,121
￥1,753,121 total
includes taxes & fees
Jan 25 - Jan 26
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
Outdoor spa tub

Villa in Toscana

Villa Dei Pavoni - Luxury Villa on top of hills in Florence
10.0 out of 10, Exceptional, (1 review)
"The host was amazing! The property was beautiful. All was seamless! All of our needs were met. Highly recommend! "
United States
Leopard I.
The price is ￥328,158
￥373,275 total
includes taxes & fees
Jan 25 - Jan 26
Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Exterior

Villa in Colle Val D'Elsa

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
The price is ￥2,172,986
￥2,172,986 total
includes taxes & fees
Jan 26 - Jan 27
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Pool

Villa in Radda in Chianti

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
10.0 out of 10, Exceptional, (1 review)
"Pros: Świetna lokalizacja i przyjemne otoczenie domu. Dom położony na wzniesieniu z którego roztaczał się piękny widok. Cons: Osoba opiekująca się domem nie mówiła po angielsku co utrudniało komunikację. Nie byliśmy świadomi że dom podzielony jest na 2 części góra i piwnica w której były dodatkowe 3 pokoje. Uszkodzona pralka która nie dopierała pranych ubrań - brudna woda z zanieczyszczeniami które dodatkowo brudziły ubrania."
Poland
Anonymous traveler
The price is ￥323,388
￥441,002 total
includes taxes & fees
Jan 27 - Jan 28
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Exterior

Villa in Monsummano Terme PT

Villa Le Terme with Pool, Whirlpool, Garden, Terrace, BBQ, A/C & Wi-Fi
8.0 out of 10, Very Good, (1 review)
"Cons: Badet tilhørende soverom nede, burde vært i bedre stand"
Denmark
Anonymous traveler
The price is ￥494,065
￥546,900 total
includes taxes & fees
Jan 26 - Jan 27
Villa Le Terme with Pool, Whirlpool, Garden, Terrace, BBQ, A/C & Wi-Fi
Pool

Villa in Montespertoli

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
10.0 out of 10, Exceptional, (1 review)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
The price is ￥295,011
￥295,379 total
includes taxes & fees
Feb 1 - Feb 2
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Outdoor dining

Villa in Signa

Casa dei Renai by Rentbeat
The price is ￥8,559
￥44,879 total
includes taxes & fees
Feb 22 - Feb 23
Casa dei Renai by Rentbeat
TV

Villa in San Jacopo Al Girone

Tolomei Gucci - Luxury Lemon House with Spa
10.0 out of 10, Exceptional, (1 review)
"Tutto perfetto……non aggiungo altro."
Italy
Giuseppe F.
The price is ￥20,089
￥44,933 total
includes taxes & fees
Jan 25 - Jan 26
Tolomei Gucci - Luxury Lemon House with Spa
Exterior

Villa in Montespertoli

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
10.0 out of 10, Exceptional, (12 reviews)
"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"
United States
Elise D.
The price is ￥235,714
￥269,598 total
includes taxes & fees
Jan 25 - Jan 26
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Property grounds

Villa in Pontassieve

VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34
10.0 out of 10, Exceptional, (2 reviews)
"This place is magical!!!!! The host was amazing and so communicative - readily available on the property and was able to answer questions as well as drive us to get food in town and to the train station! Ample space for guests and the property is beautiful. The pool area is great and comes with fun floats / fun activities for near the pool. The ambiance of the outdoor dining area is lovely and the check in/out process was easy. Couldn’t recommend this place more!!!"
United States
Lyndsey S.
The price is ￥547,850
￥639,926 total
includes taxes & fees
Jan 25 - Jan 26
VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34
Pool

Villa in Castellina in Chianti

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
The price is ￥865,604
￥957,680 total
includes taxes & fees
Jan 26 - Jan 27
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Exterior

Villa in Montespertoli

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
10.0 out of 10, Exceptional, (38 reviews)
"Excellent in every way. Highly recommend"
United States
Ed M.
The price is ￥239,397
￥273,834 total
includes taxes & fees
Jan 25 - Jan 26
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Outdoor dining

Villa in Impruneta

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
10.0 out of 10, Exceptional, (3 reviews)
"Pictures do not do it justice, this house and location is absolutely beautiful. Very comfortable beds, clean house, beauty views, nice fireplace.owner goes above and beyond to make you feel welcome. She had her local wine, cooked us a delishes breakfast, and also brought her olive oil to do tasting. We will definitely be back, i thank you for an amazing experience and a beautiful house."
United States
Lidija M.
The price is ￥64,011
￥82,242 total
includes taxes & fees
Jan 25 - Jan 26
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Property grounds

Villa in Siena

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
The price is ￥876,561
￥968,637 total
includes taxes & fees
Feb 1 - Feb 2
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Exterior

Villa in Careggi Rifredi

Country House with heated pool near the center
9.4 out of 10, Exceptional, (10 reviews)
"The property was outstanding and our family had a blast. It was a nice get away from the crowds in the city to enjoy the animals and greenery of the house on the farm. "
United States
Nancy P.
The price is ￥37,264
￥67,821 total
includes taxes & fees
Jan 26 - Jan 27
Country House with heated pool near the center
Pool

Villa in Gaiole in Chianti

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
The price is ￥1,095,701
￥1,187,777 total
includes taxes & fees
Jan 25 - Jan 26
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Property grounds

Villa in Rignano sull'Arno

Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
7.0 out of 10, Good, (2 reviews)
"We arrived after dark, tired from long overnight flight. We had no water pressure upstairs and no hot water anywhere. This was corrected the next day. One on-suite toilette would not flush properly and leaked at the grinder motor. A "tech" was called in. He informed us that he could not fix it, they would need to call someone else. When we continued to report the issue to the host, she informed us that the "tech" said it was working OK. The "tech" informed us that it was not but he could not fix...
United States
Norman C.
The price is ￥426,872
￥528,682 total
includes taxes & fees
Jan 28 - Jan 29
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
Property grounds

Villa in Gaiole in Chianti

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
10.0 out of 10, Exceptional, (8 reviews)
"Country location but easy access to a great local winery/restaurant and the town of Gaiole."
Canada
russ h.
The price is ￥191,425
￥195,845 total
includes taxes & fees
Jan 27 - Jan 28
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Terrace/patio

Villa in Castellina in Chianti

Viniard Villa - Residence Le Rose in Chianti
The price is ￥58,928
￥119,587 total
includes taxes & fees
Jan 29 - Jan 30
Viniard Villa - Residence Le Rose in Chianti
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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Top San Casciano in Val di Pesa Hotel Reviews

Orto De Medici Hotel

Orto De Medici Hotel

10/10 Excellent
"Wonderful room, clean and modern. The staff is excellent and especially the breakfast staff."
Brook 4-night trip
Posted 1 day ago
Orto De Medici Hotel

Find out more about San Casciano in Val di Pesa

San Casciano in Val di Pesa Villas information

Number of reviews
50
Accommodation
1896 Villas
Lowest Price
￥44,879
Highest Price
￥1,753,121

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 ￥44,879 and ￥1,753,121 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 1896 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.
How can I find cheap villas in San Casciano in Val di Pesa?
Expedia is here to help you look for cheap villas in San Casciano in Val di Pesa. Use our filter tool to select amenities, budget and star rating to refine your search and find a fantastic place to stay in a couple of clicks.
What is there to do near my villa in San Casciano in Val di Pesa?
After you've unpacked your things and settled in, get out and explore the incredible things San Casciano in Val di Pesa has to offer. Antinori nel Chianti Classico is a popular attraction to add to your must-do list.