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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for San Casciano in Val di Pesa villas

An open wooden door leading to a balcony with a round table and two chairs, overlooking a garden with trees and flowers.

1. Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~

Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~
Impruneta
10.0 out of 10, Exceptional, (4 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.
Florence‼️~Entire villa in the hills, sleeps 7, 4 bathrooms~
A stone building with a large arched entrance, potted plants, and outdoor seating.

2. 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 €1,024
includes taxes & fees
3 Nov - 4 Nov
Exclusive Estate | Personal Concierge & Heated Pool
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

3. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (152 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 €347
includes taxes & fees
1 Nov - 2 Nov
Luxury Villa in the Florentine hills
A villa with a swimming pool, surrounded by lush greenery and vineyards.

4. 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 €5,404
includes taxes & fees
2 Nov - 3 Nov
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
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 €135
includes taxes & fees
1 Nov - 2 Nov
Rooster House, Cooking Classes, and Opera
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

6. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is €14,160
includes taxes & fees
1 Nov - 2 Nov
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

7. 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 €1,460
includes taxes & fees
1 Dec - 2 Dec
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A courtyard with a building, potted plants, and a grassy area.

8. SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
Toscana
The price is €2,238
includes taxes & fees
2 Nov - 3 Nov
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
A garden with potted plants and a metal fence, overlooking a valley with mountains in the distance.

9. Golden Hour - Wedding in Florence

Golden Hour - Wedding in Florence
Toscana
The price is €3,097
includes taxes & fees
2 Nov - 3 Nov
Golden Hour - Wedding in Florence
A building with a large entrance, potted plants, and a statue in the foreground.

10. 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 €1,622
includes taxes & fees
2 Nov - 3 Nov
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A poolside area with lounge chairs and a pergola.

11. Bagno a Ripoli, Italy. Entire property: Villa

Bagno a Ripoli, Italy. Entire property: Villa
Toscana
The price is €784
includes taxes & fees
2 Nov - 3 Nov
Bagno a Ripoli, Italy. Entire property: Villa
An outdoor seating area with a sofa, chairs, and a table, surrounded by greenery and a stone wall.

12. Florence Apartments - Villa Fonte Morgana with Pool

Florence Apartments - 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.
Florence Apartments - Villa Fonte Morgana with Pool
A modern poolside area with a clear view of the landscape.

13. Aureva Tuscany, modern villa with private pool

Aureva Tuscany, modern villa with private pool
Montelupo F.no
The price is €590
includes taxes & fees
1 Nov - 2 Nov
Aureva Tuscany, modern villa with private pool
A covered balcony with a brick railing, a bench, and a view of lush greenery.

14. 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 €1,278
includes taxes & fees
1 Dec - 2 Dec
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

15. 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 €353
includes taxes & fees
14 Nov - 15 Nov
Villa Montecastello
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.

16. 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 €456
includes taxes & fees
1 Nov - 2 Nov
Villa Il Signorino
A hot tub with a wooden exterior, surrounded by lush greenery and a scenic view of hills.

17. Villa Dei Pavoni - Luxury Villa in the Hills of Florence

Villa Dei Pavoni - Luxury Villa in the Hills of 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.
Villa Dei Pavoni - Luxury Villa in the Hills of Florence
A large, historic building with a tower, multiple arches, and a courtyard with outdoor seating.

18. 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 €9,440
includes taxes & fees
1 Nov - 2 Nov
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
A pool area with a stone archway, lounge chairs, and a stone wall with greenery behind.

19. Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
Rignano sull'Arno
The price is €5,110
includes taxes & fees
1 Nov - 2 Nov
Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
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 Market Urban Hotel

The Market Urban Hotel

10/10 Excellent
"Nice breakfast, clean room."
Ee Tuan 5-night trip
Posted less than an hour ago
The Market Urban Hotel

Find out more about San Casciano in Val di Pesa

San Casciano in Val di Pesa Villas information

Number of reviews
325
Accommodation
1651 Villas
Lowest Price
€135
Highest Price
€14,160

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 €14,160 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 1651 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.