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
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 holiday 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 6.699.569 ₫
7.490.945 ₫ total
includes taxes & fees
20 Aug - 21 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 3.276.933 ₫
3.726.045 ₫ total
includes taxes & fees
1 Sept - 2 Sept
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 3.016.373 ₫
3.439.233 ₫ total
includes taxes & fees
19 Aug - 20 Aug
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
Courtyard

4. 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 2.534.652 ₫
3.151.784 ₫ total
includes taxes & fees
11 Aug - 12 Aug
I Parigi Corbinelli
Deluxe Double Room (1° floor) | Egyptian cotton sheets, premium bedding, down duvets

5. 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 2.098.954 ₫
2.672.516 ₫ total
includes taxes & fees
9 Aug - 10 Aug
Sette Angeli Rooms
Property amenity

6. 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 1.465.306 ₫
1.702.901 ₫ total
includes taxes & fees
30 Aug - 31 Aug
hu Firenze Certosa camping in town
Property grounds

7. 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 1.793.674 ₫
2.094.460 ₫ total
includes taxes & fees
20 Aug - 21 Aug
Domus il Palio B&B
Exterior

8. 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 4.704.986 ₫
5.327.259 ₫ total
includes taxes & fees
6 Sept - 7 Sept
Antico Borgo il Cardino
Garden view

9. 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 2.862.728 ₫
3.331.129 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Villa San Filippo
Balcony

10. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is 2.849.494 ₫
4.045.087 ₫ total
includes taxes & fees
7 Aug - 8 Aug
Palazzo al Torrione 2
View from room

11. 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 2.373.052 ₫
2.671.066 ₫ total
includes taxes & fees
9 Aug - 10 Aug
Chianti Village Morrocco
Exterior

12. 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 7.209.253 ₫
8.173.017 ₫ total
includes taxes & fees
9 Aug - 10 Aug
Borgo Argenina
Restaurant

13. 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 3.933.976 ₫
4.418.437 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Relais Villa Olmo
Free daily buffet breakfast

14. 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 8.270.289 ₫
9.218.737 ₫ total
includes taxes & fees
7 Aug - 8 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 Lavagnini

The Social Hub Florence Lavagnini

10/10 Excellent
"Beautiful hotel, great rooftop"
Daniel 2-night trip
Posted 3 hours ago
The Social Hub Florence Lavagnini

Frequently asked questions

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

Yes, there are holiday rentals close to the most popular sights in San Casciano in Val di Pesa, or you can select a more secluded option if you're looking for a relaxing 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 coffee shops during your trip.

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

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

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 holiday rentals like in San Casciano in Val di Pesa?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in San Casciano in Val di Pesa. Holiday rentals offer extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a small group gathering.