A vineyard with rows of grapevines on rolling hills, a small house, and a mountain range in the background.

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for San Casciano in Val di Pesa villas

Exterior

1. Villa Il Conventino with pool and Wi-Fi

Villa Il Conventino with pool and Wi-Fi
San Casciano in Val di Pesa
The price is €3,574
includes taxes & fees
1 Aug - 2 Aug
Villa Il Conventino with pool and Wi-Fi
Outdoor dining

2. Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi

Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
Mercatale Val Di Pesa
The price is €1,486
includes taxes & fees
22 Aug - 23 Aug
Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
Property grounds

3. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is €135
includes taxes & fees
1 Aug - 2 Aug
Rooster House, cooking classes and opera
Outdoor dining

4. 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)
"Super quaint, beatiful, designed, comfortable, not lacking anything house and location. Very informative and accessable host. Listen to the instructions on how to go to Firenze. No need to take your car tyere!"
United States
Maria H.
The price is €365
includes taxes & fees
12 Aug - 13 Aug
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Outdoor dining

5. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (148 reviews)
"Lovely property, nicely appointed, would be happy to stay there again."
United States
David K.
The price is €382
includes taxes & fees
29 Aug - 30 Aug
Luxury Villa in the Florentine hills
Exterior

6. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is €14,160
includes taxes & fees
31 Aug - 1 Sept
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Exterior

7. 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, (40 reviews)
"Absolutely fabulous! Beautiful location, exceptional host and the Tuscan countryside dream. Room for all 11 of our ladies, dreamy grounds. We all felt like we were living our Eat, Love, Pray best life!"
United States
Krista G.
The price is €1,923
includes taxes & fees
6 Aug - 7 Aug
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Exterior

8. NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!

NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!
Oltrarno
10.0 out of 10, Exceptional, (1 review)
"Struttura a dir poco fantastica. Siamo stati non bene benissimo e sicuramente ci ritorneremo.Approfitto anche per fare un ringraziamento a Serena e Venita per l’immensa disponibilità, professionalità e cordialità ricevuta."
United States
Giuseppe F.
The price is €802
includes taxes & fees
1 Aug - 2 Aug
NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!
Terrace/patio

9. Apartments Florence - Villa Fonte Morgana with pool

Apartments Florence - Villa Fonte Morgana with pool
Impruneta
10.0 out of 10, Exceptional, (1 review)
"What a beautiful villa! We thoroughly enjoyed our stay in Tuscan countryside. All rooms were comfortable and large. We were surprised by the lack of body soap and shampoo."
United States
Christine B.
Apartments Florence - Villa Fonte Morgana with pool
Pool

10. "Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Certaldo
The price is €9,891
includes taxes & fees
13 Aug - 14 Aug
"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Exterior

11. Luxury Tuscan Estate | Heated Pool & Private Concierge

Luxury Tuscan Estate | Heated Pool & Private Concierge
impruneta
10.0 out of 10, Exceptional, (111 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 €1,560
includes taxes & fees
21 Aug - 22 Aug
Luxury Tuscan Estate | Heated Pool & Private Concierge
Terrace/patio

12. Golden Hour - wedding in Florence

Golden Hour - wedding in Florence
Toscana
Golden Hour - wedding in Florence
Exterior

13. 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 €2,342
includes taxes & fees
2 Aug - 3 Aug
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Exterior

14. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is €520
includes taxes & fees
4 Aug - 5 Aug
Villa Il Signorino
Villa, Air conditioning, Courtyard View | Exterior

15. Villa Montecastello

Villa Montecastello
Monteriggioni
7.0 out of 10, Good, (2 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is €185
includes taxes & fees
3 Aug - 4 Aug
Villa Montecastello
Pool

16. Bagno a Ripoli, Italy. Entire accommodation: villa

Bagno a Ripoli, Italy. Entire accommodation: villa
Toscana
The price is €815
includes taxes & fees
7 Aug - 8 Aug
Bagno a Ripoli, Italy. Entire accommodation: villa
Property grounds

17. Villa "Toscana A Fiesole" with Private Garden and Wi-Fi

Villa "Toscana A Fiesole" with Private Garden and Wi-Fi
Firenze
8.0 out of 10, Very good, (2 reviews)
"We had great expectations for our stay in Florence, and the communication with Stefania was great, the property has a lot of potential to be a great location, but is currently not as nice as explained. While the rooms are large and spacious, upon entering the space smelled like urine, we aired it out and sprayed multiple scents to assist, but it was tough. By opening the windows, it got better by the end of day 2... however that let in bugs and we got bitten up by mulitple spiders or mosquitos...
United States
Katie M.
The price is €245
includes taxes & fees
1 Aug - 2 Aug
Villa "Toscana A Fiesole" with Private Garden and Wi-Fi
Outdoor spa tub

18. 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 €2,278
includes taxes & fees
29 Aug - 30 Aug
Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Exterior

19. My Exclusive Italy - Classic Suite in a Luxury Wine Estate

My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Rignano sull'Arno
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Terrace/patio

20. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Certaldo - Firenze
2.0 out of 10, (1 review)
"House is very nice and clean , but not equipped for rental, kitchen is poorly equipped, towels are like napkins , no toilet paper, no soap , nothing "
United States
Kelly C.
The price is €594
includes taxes & fees
2 Aug - 3 Aug
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
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

Hotel Calimala Florence

Hotel Calimala Florence

10/10 Excellent
"Perfect location to everything ! Staff was very helpful and quick to respond to all questions . I will be back ."
Annemarie 3-night trip
Posted 1 hour ago
Hotel Calimala Florence

Find out more about San Casciano in Val di Pesa

San Casciano in Val di Pesa Villas information

Number of reviews
314
Accommodation
1782 Villas
Lowest Price
€135
Highest Price
€13,027

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 €135 and €13,027 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 1782 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.