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. Premorae - Tenuta corte dell'Angelo - heated pool and concierge service

Premorae - Tenuta corte dell'Angelo - heated pool and concierge service
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 4,535
AED 5,130 total
includes taxes & fees
18 Nov - 19 Nov
Premorae - Tenuta corte dell'Angelo - heated pool and concierge service

2. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is AED 57,330
AED 57,330 total
includes taxes & fees
15 Nov - 16 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 21,863
AED 21,879 total
includes taxes & fees
15 Nov - 16 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 445
AED 502 total
includes taxes & fees
16 Nov - 17 Nov
Rooster House, Cooking Classes, and Opera

5. 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 5,263
AED 5,684 total
includes taxes & fees
29 Nov - 30 Nov
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

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 5,061
AED 5,717 total
includes taxes & fees
9 Dec - 10 Dec
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

7. Golden Hour - Wedding in Florence

Golden Hour - Wedding in Florence
Toscana
The price is AED 11,134
AED 11,984 total
includes taxes & fees
16 Nov - 17 Nov
Golden Hour - Wedding in Florence

8. 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 6,559
AED 6,567 total
includes taxes & fees
16 Nov - 17 Nov
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

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

Bagno a Ripoli, Italy. Entire property: Villa
Toscana
The price is AED 2,806
AED 3,020 total
includes taxes & fees
16 Nov - 17 Nov
Bagno a Ripoli, Italy. Entire property: Villa

10. 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 38,220
AED 38,220 total
includes taxes & fees
15 Nov - 16 Nov
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

11. VILLA GRAND MEDICI - Eight Bedroom Villa, Sleeps 16

VILLA GRAND MEDICI - Eight Bedroom Villa, Sleeps 16
Firenze
The price is AED 8,599
AED 8,599 total
includes taxes & fees
15 Nov - 16 Nov
VILLA GRAND MEDICI - Eight Bedroom Villa, Sleeps 16

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

13. 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 6,413
AED 6,903 total
includes taxes & fees
16 Nov - 17 Nov
Villa Dei Pavoni - Luxury Villa in the Hills of Florence

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 AED 4,213
AED 4,706 total
includes taxes & fees
15 Nov - 16 Nov
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

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 11,660
AED 19,211 total
includes taxes & fees
15 Nov - 16 Nov
Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

16. Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence

Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence
Oltrarno
The price is AED 6,284
AED 6,332 total
includes taxes & fees
1 Dec - 2 Dec
Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence

17. 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 13,377
AED 15,401 total
includes taxes & fees
16 Nov - 17 Nov
VILLA FIESOLANA - Twelve Bedroom Villa, Sleeps 34

18. 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 1,287
AED 1,428 total
includes taxes & fees
28 Nov - 29 Nov
Villa Montecastello

19. 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 28,665
AED 30,689 total
includes taxes & fees
15 Nov - 16 Nov
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

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 4,197
AED 6,184 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 502 and AED 57,330 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?
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How can I find cheap villas in San Casciano in Val di Pesa?
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