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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for San Casciano in Val di Pesa villas

Outdoor dining

1. Molino In Chianti - Villa with Private Pool

Molino In Chianti - Villa with Private Pool
Mercatale Val Di Pesa
The price is €1,387
includes taxes & fees
16 Sept - 17 Sept
Molino In Chianti - Villa with Private Pool
Outdoor dining

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

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Impruneta
10.0 out of 10, 3, (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 €383
includes taxes & fees
16 Sept - 17 Sept
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Exterior

3. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Montespertoli
The price is €6,004
includes taxes & fees
14 Oct - 15 Oct
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Property grounds

4. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is €135
includes taxes & fees
15 Sept - 16 Sept
Rooster House, cooking classes and opera
Outdoor dining

5. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, 149, (149 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
The price is €339
includes taxes & fees
12 Oct - 13 Oct
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 €13,027
includes taxes & fees
15 Sept - 16 Sept
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Property grounds

7. Villino Tre Pini | Panoramic Private Pool, Nature & Privacy

Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Tavarnelle Val di Pesa
10.0 out of 10, 1, (1 review)
The price is €844
includes taxes & fees
4 Oct - 5 Oct
Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Pool

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

"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Certaldo
The price is €5,523
includes taxes & fees
12 Oct - 13 Oct
"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Terrace/patio

9. Tenuta le Viste - beautiful Villa overlooking Florence

Tenuta le Viste - beautiful Villa overlooking Florence
scandicci
9.6 out of 10, 4, (4 reviews)
"Beautiful house"
France
STEPHANE B.
Tenuta le Viste - beautiful Villa overlooking Florence
Terrace/patio

10. Golden Hour - wedding in Florence

Golden Hour - wedding in Florence
Toscana
The price is €3,128
includes taxes & fees
30 Sept - 1 Oct
Golden Hour - wedding in Florence
Exterior

11. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, 113, (113 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 €1,063
includes taxes & fees
1 Oct - 2 Oct
Exclusive Estate | Personal Concierge & Heated Pool
Exterior

12. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Montespertoli
10.0 out of 10, 41, (41 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 €1,854
includes taxes & fees
15 Sept - 16 Sept
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Pool

13. Villa Sunset, in the heart of Chianti

Villa Sunset, in the heart of Chianti
Greve in Chianti
8.0 out of 10, 1, (1 review)
"La casa é spaziosa ed accogliente e molto pulita in una posizione e strategica e comoda per visitare Firenze e i borghi della zona. "
Italy
elisa b.
Villa Sunset, in the heart of Chianti
Terrace/patio

14. Apartments Florence - Villa Fonte Morgana with pool

Apartments Florence - Villa Fonte Morgana with pool
Impruneta
10.0 out of 10, 1, (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
Exterior

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

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
10.0 out of 10, 1, (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 €1,982
includes taxes & fees
30 Sept - 1 Oct
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Villa, Air conditioning, Courtyard View | Exterior

16. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, 3, (3 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 €167
includes taxes & fees
15 Sept - 16 Sept
Villa Montecastello
Pool

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

Bagno a Ripoli, Italy. Entire accommodation: villa
Toscana
The price is €783
includes taxes & fees
22 Sept - 23 Sept
Bagno a Ripoli, Italy. Entire accommodation: villa
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, 1, (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 €2,023
includes taxes & fees
18 Sept - 19 Sept
Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Exterior

19. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, 3, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is €457
includes taxes & fees
15 Sept - 16 Sept
Villa Il Signorino
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

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

10/10 Excellent
"This was a good location close to the train station and city center with a short walk. The amenities or the washer and dryer, you can only use one machine at a time which slows the process down. Additionally the pool is only open from 9am - 6 pm and it would be more helpful to have a wider range of hours. The staff was extremely helpful and kind."
Loren 3-night trip
Posted less than an hour ago
The Social Hub Florence Lavagnini

Find out more about San Casciano in Val di Pesa

San Casciano in Val di Pesa Villas information

Number of reviews
3
Accommodation
1736 Villas
Lowest Price
€167
Highest Price
€167

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 €167 and €167 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 1736 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.