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

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Our top choices for San Casciano in Val di Pesa villas

1. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (117 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 3,597
AED 4,128 total
includes taxes & fees
4 Nov - 5 Nov
Exclusive Estate | Personal Concierge & Heated Pool

2. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is AED 58,215
AED 58,215 total
includes taxes & fees
4 Nov - 5 Nov
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

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 AED 22,201
AED 22,217 total
includes taxes & fees
4 Nov - 5 Nov
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

4. Rooster House, Cooking Classes, and Opera

Rooster House, Cooking Classes, and Opera
Tavarnelle Val di Pesa
The price is AED 451
AED 508 total
includes taxes & fees
27 Nov - 28 Nov
Rooster House, Cooking Classes, and Opera

5. 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 6,763
AED 7,743 total
includes taxes & fees
4 Nov - 5 Nov
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

6. 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 5,345
AED 5,817 total
includes taxes & fees
29 Nov - 30 Nov
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

7. 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 AED 8,223
AED 8,942 total
includes taxes & fees
4 Nov - 5 Nov
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

8. Golden Hour - Wedding in Florence

Golden Hour - Wedding in Florence
Toscana
The price is AED 11,306
AED 12,272 total
includes taxes & fees
5 Nov - 6 Nov
Golden Hour - Wedding in Florence

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

Bagno a Ripoli, Italy. Entire property: Villa
Toscana
The price is AED 2,849
AED 3,092 total
includes taxes & fees
4 Nov - 5 Nov
Bagno a Ripoli, Italy. Entire property: Villa

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 AED 6,660
AED 6,668 total
includes taxes & fees
5 Nov - 6 Nov
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

11. 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 38,810
AED 38,810 total
includes taxes & fees
4 Nov - 5 Nov
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

12. 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 6,512
AED 7,067 total
includes taxes & fees
4 Nov - 5 Nov
Villa Dei Pavoni - Luxury Villa in the Hills of Florence

13. 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 4,278
AED 4,779 total
includes taxes & fees
8 Nov - 9 Nov
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

14. 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

15. 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 AED 11,840
AED 20,454 total
includes taxes & fees
4 Nov - 5 Nov
Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

16. VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34

VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34
Pontassieve
10.0 out of 10, Exceptional, (2 reviews)
"This place is magical!!!!! The host was amazing and so communicative - readily available on the property and was able to answer questions as well as drive us to get food in town and to the train station! Ample space for guests and the property is beautiful. The pool area is great and comes with fun floats / fun activities for near the pool. The ambiance of the outdoor dining area is lovely and the check in/out process was easy. Couldn’t recommend this place more!!!"
United States
Lyndsey S.
The price is AED 13,584
AED 15,639 total
includes taxes & fees
4 Nov - 5 Nov
VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34

17. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
Siena
10.0 out of 10, Exceptional, (1 review)
"We celebrated our 20th Anniversary with 23 guests, all who stayed at the Property. The location and accommodations could not have been better and the staff and property manager were excellent. I would highly recommend staying here for any Tuscany adventures! Thank you so much to the owner and all involved!Ron and Wendy"
United States
Ron M.
The price is AED 29,108
AED 31,163 total
includes taxes & fees
4 Nov - 5 Nov
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

18. Country house with a heated pool near the town center

Country house with a heated pool near the town center
Careggi Rifredi
9.8 out of 10, Exceptional, (19 reviews)
"A truly unique and cozy place near Florence surrounded by nature yet only 15 minutes from the city centre. The house has a lot of charm and character. A special highlight is the small underground pool - perfect for relaxing after a day in Florence. Giacomo was very friendly responsive and a wonderful host throughout our stay."
United States
Jeannette B.
The price is AED 1,110
AED 1,727 total
includes taxes & fees
4 Nov - 5 Nov
Country house with a heated pool near the town center

19. La Limonaia di Villa Aurora - Sweet Dreams in Florence

La Limonaia di Villa Aurora - Sweet Dreams in Florence
Le Cure
The price is AED 11,795
AED 17,933 total
includes taxes & fees
4 Nov - 5 Nov
La Limonaia di Villa Aurora - Sweet Dreams in Florence

20. "A Casa di Franca Villa con piscina"

"A Casa di Franca Villa con piscina"
Gambassi Terme
10.0 out of 10, Exceptional, (1 review)
"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...
Spain
Anonymous traveler
The price is AED 4,262
AED 6,280 total
includes taxes & fees
15 Nov - 16 Nov
"A Casa di Franca Villa con piscina"
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

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 508 and AED 58,215 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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