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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for San Casciano in Val di Pesa villas

An outdoor patio with a round table, chairs, a sofa, and a potted plant.

1. Molino In Chianti - Villa with Private Pool

Molino In Chianti - Villa with Private Pool
Mercatale Val Di Pesa
The price is £1,179
includes taxes & fees
5 Oct - 6 Oct
Molino In Chianti - Villa with Private Pool
An open wooden door leading to a balcony with a round table and two chairs, overlooking a garden with trees and flowers.

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, 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 £333
includes taxes & fees
13 Oct - 14 Oct
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

3. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is £11,073
includes taxes & fees
5 Oct - 6 Oct
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

4. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (150 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 £287
includes taxes & fees
1 Nov - 2 Nov
Luxury Villa in the Florentine hills
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

5. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is £114
includes taxes & fees
6 Oct - 7 Oct
Rooster House, cooking classes and opera
A stone building with a large arched entrance, potted plants, and outdoor seating.

6. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (115 reviews)
"We had a great time with the family in impruneta. Caterine - the host - was very friendly and made everything to have a perfect stay in the villa. We can absolutely recommend this villa !"
Germany
Oli P.
The price is £954
includes taxes & fees
26 Oct - 27 Oct
Exclusive Estate | Personal Concierge & Heated Pool
A villa with a swimming pool, surrounded by lush greenery and vineyards.

7. 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 £5,103
includes taxes & fees
14 Oct - 15 Oct
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Terrace/patio

8. Tenuta le Viste - beautiful Villa overlooking Florence

Tenuta le Viste - beautiful Villa overlooking Florence
scandicci
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful house"
France
STEPHANE B.
Tenuta le Viste - beautiful Villa overlooking Florence
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

9. 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, Exceptional, (42 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 £1,664
includes taxes & fees
1 Nov - 2 Nov
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

10. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (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 £142
includes taxes & fees
6 Oct - 7 Oct
Villa Montecastello
A stone patio with outdoor furniture, a stone wall, and a view of the countryside.

11. Golden Hour - wedding in Florence

Golden Hour - wedding in Florence
Toscana
The price is £2,624
includes taxes & fees
5 Oct - 6 Oct
Golden Hour - wedding in Florence
A building with a large entrance, potted plants, and a statue in the foreground.

12. 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 £1,532
includes taxes & fees
1 Nov - 2 Nov
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Pool

13. Villa Sunset, in the heart of Chianti

Villa Sunset, in the heart of Chianti
Greve in Chianti
8.0 out of 10, Very good, (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
A poolside area with lounge chairs and a pergola.

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

Bagno a Ripoli, Italy. Entire accommodation: villa
Toscana
The price is £666
includes taxes & fees
5 Oct - 6 Oct
Bagno a Ripoli, Italy. Entire accommodation: villa
A covered balcony with a brick railing, a bench, and a view of lush greenery.

15. 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 £495
includes taxes & fees
5 Oct - 6 Oct
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A two-story building with a red roof, multiple windows, and a gravel driveway.

16. Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi

Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
Empoli
10.0 out of 10, Exceptional, (1 review)
"The villa is divided into 4 apartments and was perfect for our group of eleven. The property was beautiful and it is convenient to the Empoli train station."
United States
Vicki C.
The price is £1,414
includes taxes & fees
6 Oct - 7 Oct
Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
A hot tub with a wooden exterior, surrounded by lush greenery and a scenic view of hills.

17. 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, (2 reviews)
"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 £1,694
includes taxes & fees
5 Oct - 6 Oct
Villa Dei Pavoni - Luxury Villa on top of hills in Florence
A two-story building with a stone staircase leading to a wooden door. There is a small outdoor table and a potted plant on the porch.

18. 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 £387
includes taxes & fees
6 Oct - 7 Oct
Villa Il Signorino
A two-story building with a garden, a gazebo, and a statue.

19. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Gambassi Terme
The price is £3,665
includes taxes & fees
7 Oct - 8 Oct
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
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
"We loved everything about this hotel. They had world class service from morning to night. We had a wonderful introduction to the hotel and a personal escort to our room. The breakfast was lovely, with a nice selection of premium products, and a beautiful dining room with china. We highly recommend Hotel Bernini, it was the perfect hotel in a perfect location."
Denise 4-night trip
Posted 3 hours ago
Bernini Palace

Find out more about San Casciano in Val di Pesa

San Casciano in Val di Pesa Villas information

Number of reviews
326
Accommodation
1736 Villas
Lowest Price
£114
Highest Price
£11,073

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 £114 and £11,073 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.