Panoramic view of beautiful rows of colored vineyards nella campagna toscana in the Chianti region near San Casciano in Val di Pesa. Autumn season in October. Italy.

Search Holiday Rentals in San Casciano in Val di Pesa

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
The price is 7.533.307 ₫
8.407.390 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Villa il Fedino

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 2.937.249 ₫
3.351.726 ₫ total
includes taxes & fees
5 Jul - 6 Jul
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

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 3.519.660 ₫
3.992.378 ₫ total
includes taxes & fees
23 Jun - 24 Jun
B&B La Fonte del Machiavelli

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (75 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 8.224.889 ₫
9.168.130 ₫ total
includes taxes & fees
24 Jun - 25 Jun
Terre di Baccio

San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
10.0 out of 10, Exceptional, (435 reviews)
"This place was so beautiful and in a great location. The staff went above and beyond to make sure our stay was perfect. We were very happy with our choice of accommodations for our first time in Italy and it would be our choice when we return."
United States
TIFFANY
The price is 4.578.028 ₫
5.398.239 ₫ total
includes taxes & fees
13 Jul - 14 Jul
San Giuliano Inn - Adults Only

Maison Ginori Guelfa

Maison Ginori Guelfa
Historic Centre of Florence
10.0 out of 10, Exceptional, (29 reviews)
"Clean room, amazing staff and service. Would highly recommend to anyone! "
United States
Neil
The price is 6.001.946 ₫
6.964.398 ₫ total
includes taxes & fees
3 Jul - 4 Jul
Maison Ginori Guelfa

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (23 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
The price is 8.030.039 ₫
9.074.548 ₫ total
includes taxes & fees
23 Jun - 24 Jun
Borgo Argenina

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location and beautiful room. Staff weren't that friendly but I think it would have been better if we spoke Italian."
Canada
Sophie
The price is 2.833.851 ₫
4.022.880 ₫ total
includes taxes & fees
25 Jun - 26 Jun
Palazzo al Torrione 2

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (246 reviews)
"Delightful location, comfortable bed, excellent food."
Canada
Rupert
The price is 3.393.693 ₫
3.823.626 ₫ total
includes taxes & fees
22 Jul - 23 Jul
Relais Villa Olmo

DomuS Miniato

DomuS Miniato
San Miniato
10.0 out of 10, Exceptional, (1 review)
"Kjempefint rom, nydelig utsikt og hyggelig vertsskap. Anbefales. "
Norway
Karen
The price is 2.809.668 ₫
3.151.011 ₫ total
includes taxes & fees
6 Jul - 7 Jul
DomuS Miniato

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (321 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
Hu Norcenni Girasole Village

Serristori Palace Residence

Serristori Palace Residence
Historic Centre of Florence
9.6 out of 10, Exceptional, (199 reviews)
"This is a must, away from hustle, great near nightlife, amazing rooms with views"
Canada
glenn
The price is 4.200.562 ₫
4.982.875 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Serristori Palace Residence

Corte Guelfa

Corte Guelfa
3.0 star property
Historic Centre of Florence
9.8 out of 10, Exceptional, (187 reviews)
"Great place to stay, close to everything you need!!!"
United States
Howard
The price is 3.780.963 ₫
4.521.316 ₫ total
includes taxes & fees
28 Jun - 29 Jun
Corte Guelfa

Numa Florence Palazzo Belfiore

Numa Florence Palazzo Belfiore
Historic Centre of Florence
9.6 out of 10, Exceptional, (396 reviews)
"Perfect location for sightseeing but also a bit of distance from all the crowds. Will definitely stay here again!"
Canada
Megan
The price is 6.641.386 ₫
7.667.782 ₫ total
includes taxes & fees
23 Jun - 24 Jun
Numa Florence Palazzo Belfiore
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.
Save an average of 15% on thousands of hotels when you're signed in

Top San Casciano in Val di Pesa Hotel Reviews

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 28 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. Uffizi Gallery and Piazza di Santa Maria Novella 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.