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 AED 3,433
AED 3,940 total
includes taxes & fees
1 Nov - 2 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 AED 817
AED 1,357 total
includes taxes & fees
1 Nov - 2 Nov
Luxury Villa in the Florentine hills
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

4. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is AED 53,242
AED 53,242 total
includes taxes & fees
29 Oct - 30 Oct
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
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 AED 450
AED 535 total
includes taxes & fees
27 Nov - 28 Nov
Rooster House, Cooking Classes, and Opera
A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

6. Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Montespertoli
10.0 out of 10, Exceptional, (12 reviews)
"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"
United States
Elise D.
The price is AED 6,744
AED 7,720 total
includes taxes & fees
2 Nov - 3 Nov
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
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
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

8. 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 AED 6,948
AED 7,937 total
includes taxes & fees
12 Nov - 13 Nov
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.

9. 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
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
Terrace/patio

10. Tenuta le Viste—a magnificent villa overlooking Florence

Tenuta le Viste—a magnificent villa overlooking Florence
scandicci
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful house"
France
STEPHANE B.
Tenuta le Viste—a magnificent villa overlooking Florence
A building with a large entrance, potted plants, and a statue in the foreground.

11. 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 AED 7,357
AED 7,365 total
includes taxes & fees
28 Nov - 29 Nov
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Pool

12. Villa Sunset, in the heart of Chianti area

Villa Sunset, in the heart of Chianti area
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 area
An outdoor seating area with a sofa, chairs, and a table, surrounded by greenery and a stone wall.

13. 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 stone patio with outdoor furniture, a stone wall, and a view of the countryside.

14. Golden Hour - Wedding in Florence

Golden Hour - Wedding in Florence
Toscana
The price is AED 11,239
AED 12,821 total
includes taxes & fees
25 Nov - 26 Nov
Golden Hour - Wedding in Florence
A poolside area with lounge chairs and a pergola.

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

Bagno a Ripoli, Italy. Entire property: Villa
Toscana
The price is AED 3,147
AED 3,494 total
includes taxes & fees
27 Nov - 28 Nov
Bagno a Ripoli, Italy. Entire property: Villa
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

16. 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 AED 670
AED 749 total
includes taxes & fees
29 Oct - 30 Oct
Villa Montecastello
A modern poolside area with a clear view of the landscape.

17. Aureva Tuscany, modern villa with private pool

Aureva Tuscany, modern villa with private pool
Montelupo F.no
Aureva Tuscany, modern villa with private pool
A covered balcony with a brick railing, a bench, and a view of lush greenery.

18. 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 AED 4,253
AED 4,751 total
includes taxes & fees
2 Nov - 3 Nov
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A large, historic building with a tower, multiple arches, and a courtyard with outdoor seating.

19. 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 AED 35,495
AED 35,495 total
includes taxes & fees
29 Oct - 30 Oct
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
A hot tub with a wooden exterior, surrounded by lush greenery and a scenic view of hills.

20. 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.
The price is AED 8,092
AED 9,241 total
includes taxes & fees
25 Nov - 26 Nov
Villa Dei Pavoni - Luxury Villa in the Hills of Florence
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

Villa Neroli - Place of Charme

Villa Neroli - Place of Charme

10/10 Excellent
"Great stay"
Bridgette 1-night trip
Posted 6 hours ago
Villa Neroli - Place of Charme

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 AED 535 and AED 53,242 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 1691 villas in San Casciano in Val di Pesa. No matter if you're traveling with the kids or organizing 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?
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