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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for San Casciano in Val di Pesa villas

Exterior

Beautiful Tuscan home between Florence & Siena

Beautiful Tuscan home between Florence & Siena
Florence
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 €1,191
includes taxes & fees
29 Jan - 30 Jan
Beautiful Tuscan home between Florence & Siena
Exterior

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
Careggi Rifredi
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 €9,520
includes taxes & fees
29 Jan - 30 Jan
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
Exterior

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is €11,800
includes taxes & fees
29 Jan - 30 Jan
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Property grounds

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is €5,260
includes taxes & fees
1 Feb - 2 Feb
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Pool

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Gaiole in Chianti
The price is €6,450
includes taxes & fees
29 Jan - 30 Jan
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Pool

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Castellina in Chianti
The price is €5,201
includes taxes & fees
29 Jan - 30 Jan
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Exterior

Villa Le Terme with Pool, Whirlpool, Garden, Terrace, BBQ, A/C & Wi-Fi

Villa Le Terme with Pool, Whirlpool, Garden, Terrace, BBQ, A/C & Wi-Fi
Monsummano Terme PT
8.0 out of 10, Very good, (1 review)
"Cons: Badet tilhørende soverom nede, burde vært i bedre stand"
Denmark
Anonymous traveller
The price is €2,970
includes taxes & fees
29 Jan - 30 Jan
Villa Le Terme with Pool, Whirlpool, Garden, Terrace, BBQ, A/C & Wi-Fi
Pool

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
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 traveller
The price is €2,395
includes taxes & fees
30 Jan - 31 Jan
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Outdoor spa tub

Villa Dei Pavoni - Luxury Villa on top of hills in Florence

Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Toscana
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 €2,038
includes taxes & fees
29 Jan - 30 Jan
Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Pool

Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
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 €1,604
includes taxes & fees
1 Feb - 2 Feb
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Outdoor dining

Casa dei Renai by Rentbeat

Casa dei Renai by Rentbeat
Signa
The price is €240
includes taxes & fees
15 Feb - 16 Feb
Casa dei Renai by Rentbeat
Property grounds

VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34

VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34
Pontassieve
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 €3,475
includes taxes & fees
29 Jan - 30 Jan
VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34
TV

Tolomei Gucci - Luxury Lemon House with Spa

Tolomei Gucci - Luxury Lemon House with Spa
San Jacopo Al Girone
10.0 out of 10, Exceptional, (1 review)
"Tutto perfetto……non aggiungo altro."
Italy
Giuseppe F.
The price is €424
includes taxes & fees
24 Feb - 25 Feb
Tolomei Gucci - Luxury Lemon House with Spa
Property grounds

Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning

Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
Rignano sull'Arno
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 €2,871
includes taxes & fees
29 Jan - 30 Jan
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
Exterior

CountryHouse con Piscina Privata 5 min dal centro

CountryHouse con Piscina Privata 5 min dal centro
Careggi Rifredi
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 €367
includes taxes & fees
29 Jan - 30 Jan
CountryHouse con Piscina Privata 5 min dal centro
Outdoor dining

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Impruneta
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 €457
includes taxes & fees
29 Jan - 30 Jan
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Exterior

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (38 reviews)
"Excellent in every way. Highly recommend"
United States
Ed M.
The price is €1,482
includes taxes & fees
29 Jan - 30 Jan
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Exterior

Villa w/ personal concierge service, heated pool only 20 min to Florence center

Villa w/ personal concierge service, heated pool only 20 min to Florence center
impruneta
10.0 out of 10, Exceptional, (106 reviews)
"The Villa and grounds are absolutely beautiful! Caterina and her family members were the most gracious hosts. They could not do enough to make sure we had a "once in a lifetime" multi-generational family trip and truly made us feel like part of their family during our stay. We loved every second of our time in Tuscany and would highly recommend this amazing property."
United States
Charles S.
The price is €1,312
includes taxes & fees
31 Jan - 1 Feb
Villa w/ personal concierge service, heated pool only 20 min to Florence center
Property grounds

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Gaiole in Chianti
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 €1,064
includes taxes & fees
29 Jan - 30 Jan
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
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

Bernini Palace

Bernini Palace

10/10 Excellent
"spotlessly clean room amazing staff fantastic breakfast "
Jason 3-night trip
Posted 2 days ago
Bernini Palace

Find out more about San Casciano in Val di Pesa

San Casciano in Val di Pesa Villas information

Number of reviews
155
Accommodation
1847 Villas
Lowest Price
€240
Highest Price
€9,520

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 €240 and €9,520 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 1847 villas in San Casciano in Val di Pesa. No matter if you're travelling with the kids or organising 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.