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

San Casciano in Val di Pesa Vacation Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for San Casciano in Val di Pesa vacation rentals

Property entrance

1. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (102 reviews)
"This is an excellent property. Very historic, rustic and with great views across the Tuscan landscapes. Lorenzo and his mother were super duper hosts who took great care of us. The property dates back to 1380 and the rooms are decorated with choicest artifacts that adds greatly to the experience. The location is fantastic too with the local market and restaurants in easy walking reach. The breakfast service is fabulous with many choices and Lorenzo himself is great chef as well! Highly recommend...
United States
Nilesh
The price is AED 887
AED 993 total
includes taxes & fees
17 Aug - 18 Aug
Villa il Fedino
Outdoor dining

2. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (83 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is AED 443
AED 504 total
includes taxes & fees
7 Sep - 8 Sep
B&B La Fonte del Machiavelli
Exterior

3. B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (27 reviews)
"The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day"
Mexico
Raymundo
The price is AED 463
AED 527 total
includes taxes & fees
31 Aug - 1 Sep
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
Pool

4. Tenuta Branca - Podere Apartment with Pool and Terrace in Chianti

Tenuta Branca - Podere Apartment with Pool and Terrace in Chianti
San Casciano in Val di Pesa
The price is AED 931
AED 1,439 total
includes taxes & fees
30 Aug - 31 Aug
Tenuta Branca - Podere Apartment with Pool and Terrace in Chianti
Pool

5. Portion of Villa Il Conventino with Pool and Wi-Fi

Portion of Villa Il Conventino with Pool and Wi-Fi
San Casciano in Val di Pesa
The price is AED 11,148
AED 15,123 total
includes taxes & fees
8 Aug - 9 Aug
Portion of Villa Il Conventino with Pool and Wi-Fi
Pool

6. Apartment 'Mini in Chianti' with Shared Pool, Wi-Fi and Air Conditioning

Apartment 'Mini in Chianti' with Shared Pool, Wi-Fi and Air Conditioning
San Casciano in Val di Pesa
The price is AED 1,626
AED 1,901 total
includes taxes & fees
8 Aug - 9 Aug
Apartment 'Mini in Chianti' with Shared Pool, Wi-Fi and Air Conditioning
Outdoor dining

7. Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi

Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
Mercatale Val Di Pesa
The price is AED 5,853
AED 5,870 total
includes taxes & fees
23 Aug - 24 Aug
Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
Pool

8. Cottage in Chianti Barn with Shared Pool, Wi-Fi, and Air Conditioning

Cottage in Chianti Barn with Shared Pool, Wi-Fi, and Air Conditioning
San Casciano in Val di Pesa
The price is AED 3,902
AED 4,177 total
includes taxes & fees
13 Aug - 14 Aug
Cottage in Chianti Barn with Shared Pool, Wi-Fi, and Air Conditioning
Courtyard

9. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (168 reviews)
"Charming place, great welcoming"
United Kingdom
Stefano
The price is AED 392
AED 483 total
includes taxes & fees
11 Aug - 12 Aug
I Parigi Corbinelli
Deluxe Double Room (1° floor) | Egyptian cotton sheets, premium bedding, down comforters

10. Sette Angeli Rooms

Sette Angeli Rooms
Historic Centre of Florence
8.8 out of 10, Excellent, (677 reviews)
"Good clean rooms and very close to the city center as well as the train station"
United Kingdom
VISHAL
The price is AED 269
AED 346 total
includes taxes & fees
10 Aug - 11 Aug
Sette Angeli Rooms
Property amenity

11. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very Good, (94 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is AED 200
AED 233 total
includes taxes & fees
30 Aug - 31 Aug
hu Firenze Certosa camping in town
Exterior

12. La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !

La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !
Siena
10.0 out of 10, Exceptional, (66 reviews)
"Super helpful host"
Australia
Robyn D.
The price is AED 603
AED 904 total
includes taxes & fees
18 Aug - 19 Aug
La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !
Property grounds

13. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (97 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
The price is AED 250
AED 292 total
includes taxes & fees
11 Aug - 12 Aug
Domus il Palio B&B
Exterior

14. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (84 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is AED 623
AED 707 total
includes taxes & fees
6 Sep - 7 Sep
Antico Borgo il Cardino
Garden view

15. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (45 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is AED 383
AED 447 total
includes taxes & fees
7 Sep - 8 Sep
Villa San Filippo
Balcony

16. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (110 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is AED 396
AED 563 total
includes taxes & fees
21 Aug - 22 Aug
Palazzo al Torrione 2
View from room

17. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (116 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is AED 371
AED 417 total
includes taxes & fees
6 Sep - 7 Sep
Chianti Village Morrocco
Exterior

18. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"A very peaceful and relaxing B&B that I highly recommend, spacious rooms , clean and well maintained! Host were very pleasing and helpful… definitely recommend!!"
Canada
Sabatino
The price is AED 976
AED 1,107 total
includes taxes & fees
9 Aug - 10 Aug
Borgo Argenina
Restaurant

19. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (258 reviews)
"Delightful location, comfortable bed, excellent food."
Canada
Rupert
The price is AED 548
AED 616 total
includes taxes & fees
30 Aug - 31 Aug
Relais Villa Olmo
Free daily buffet breakfast

20. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
United States
Julia
The price is AED 1,130
AED 1,260 total
includes taxes & fees
8 Aug - 9 Aug
Terre di Baccio
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 Social Hub Florence Belfiore

The Social Hub Florence Belfiore

10/10 Excellent
"Clean, modern, lots of amenities. Very helpful staff. Highly recommend."
Meg 4-night trip
Posted 6 hours ago
The Social Hub Florence Belfiore

Frequently asked questions

Are there vacation rentals in San Casciano in Val di Pesa?

Yes, you can find vacation rentals near popular local attractions in San Casciano in Val di Pesa, or you can choose a more remote option if you want a relaxing place to stay. Visitors to San Casciano in Val di Pesa speak positively about the countryside and wineries in this destination. Make sure you have time to check out the spas and coffeehouses during your trip.

What's the top vacation rental in San Casciano in Val di Pesa?

Villa La Stella - Casa per Ferie: This vacation home rental near San Casciano in Val di Pesa is located near the airport and has a garden, a library, and air-conditioning to put you at ease in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in San Casciano in Val di Pesa?

Choose from 27 Expedia vacation rentals in San Casciano in Val di Pesa for a memorable vacation.

What can I see and do in San Casciano in Val di Pesa?

While exploring the area, visit family-friendly sights like Villa Medicea di Lilliano - Malenchini, or get outside and enjoy nature at Boboli Gardens. Cathedral of Santa Maria del Fiore and Piazza della Signoria are other popular places to visit in the area.

What are vacation rentals like in San Casciano in Val di Pesa?

Vacation rentals are private accommodations you can book for a short or long stay in San Casciano in Val di Pesa. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips or small group gatherings.