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.

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

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

Property entrance

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
4 Jul - 5 Jul
Villa il Fedino
Exterior

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 2.870.067 ₫
3.277.826 ₫ total
includes taxes & fees
4 Jul - 5 Jul
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
Outdoor dining

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
22 Jun - 23 Jun
B&B La Fonte del Machiavelli
Romantic Double Room, 1 Bedroom, Non Smoking | View from room

B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (64 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is 3.832.518 ₫
4.366.711 ₫ total
includes taxes & fees
22 Jun - 23 Jun
B&B Palazzo Tortoli
Shower, rainfall showerhead, hair dryer, bathrobes

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
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (33 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
The price is 4.514.550 ₫
4.966.005 ₫ total
includes taxes & fees
20 Jul - 21 Jul
Villa di Sotto
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (91 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 1.877.152 ₫
2.185.619 ₫ total
includes taxes & fees
23 Jun - 24 Jun
Domus il Palio B&B
Balcony

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
Exterior

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
Deluxe Room, Patio | Frette Italian sheets, premium bedding, minibar, in-room safe

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (35 reviews)
"Great place, difficult driving access but enjoyable"
United States
Sergio
The price is 4.406.092 ₫
4.937.266 ₫ total
includes taxes & fees
24 Jun - 25 Jun
Tenuta Sant'Ilario
Garden view

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (43 reviews)
"Good location between to San Gimignano and Florence, lose to the highway."
United States
ALEXANDER
The price is 1.947.957 ₫
2.323.881 ₫ total
includes taxes & fees
26 Jun - 27 Jun
Villa San Filippo
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (115 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is 2.091.233 ₫
2.360.732 ₫ total
includes taxes & fees
28 Jun - 29 Jun
Chianti Village Morrocco
Free daily buffet breakfast

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
Superior Double Room, 1 King Bed | Premium bedding, down duvets, in-room safe, desk

La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.0 out of 10, Wonderful, (264 reviews)
"Great location in Oltrarno; clean, comfortable and well-appointed room; helpful and responsive staff. Ask for restaurant recommendations, they won’t disappoint."
United States
Robert
The price is 3.822.914 ₫
4.627.839 ₫ total
includes taxes & fees
2 Jul - 3 Jul
La Torre Del Cestello
Exterior

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
The price is 2.527.980 ₫
2.871.342 ₫ total
includes taxes & fees
25 Jun - 26 Jun
Hu Norcenni Girasole Village
Terrace/patio

Numa Florence Palazzo San Niccolò

Numa Florence Palazzo San Niccolò
Historic Centre of Florence
9.4 out of 10, Exceptional, (195 reviews)
"Wonderful spacious, spotlessly clean apartment, beautiful peaceful garden, lovely staff"
United Kingdom
Rachel
The price is 4.692.880 ₫
5.524.425 ₫ total
includes taxes & fees
22 Jun - 23 Jun
Numa Florence Palazzo San Niccolò
Restaurant

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (245 reviews)
"Delightful location, comfortable bed, excellent food."
Canada
Rupert
The price is 4.060.576 ₫
4.557.198 ₫ total
includes taxes & fees
8 Jul - 9 Jul
Relais Villa Olmo
Suite | Egyptian cotton sheets, premium bedding, in-room safe, desk

Palazzo Mannaioni Suites

Palazzo Mannaioni Suites
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (1,128 reviews)
"The management waswarm and welcoming and helped assist us with restaurants, travel and sightseeing."
United States
Janet
The price is 4.347.089 ₫
5.204.432 ₫ total
includes taxes & fees
5 Jul - 6 Jul
Palazzo Mannaioni Suites
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.4 out of 10, Very good, (250 reviews)
"Nice inn on a working farm located deep in the hills of suburban Florence."
United States
Allan
The price is 2.532.784 ₫
3.208.696 ₫ total
includes taxes & fees
28 Jun - 29 Jun
Fattoria il Milione Agriturismo
Exterior

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
5 Jul - 6 Jul
DomuS Miniato
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 Hoxton Florence

The Hoxton Florence

10/10 Excellent
"Would absolutely stay again. Close enough to everything but also not in the action. Clean and well designed!"
Annica 3-night trip
Posted 9 hours ago
The Hoxton Florence

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.