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.

San Casciano in Val di Pesa Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for San Casciano in Val di Pesa vacation 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 ₩434,953
₩485,420 total
includes taxes & fees
Jul 4 - Jul 5
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 ₩188,432
₩214,247 total
includes taxes & fees
Jun 25 - Jun 26
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, (82 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is ₩203,216
₩230,509 total
includes taxes & fees
Jun 22 - Jun 23
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 ₩228,806
₩260,402 total
includes taxes & fees
Jun 23 - Jun 24
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 ₩346,537
₩402,106 total
includes taxes & fees
Jul 3 - Jul 4
Maison Ginori Guelfa
Indoor pool, seasonal outdoor pool, pool umbrellas, sun 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 ₩261,933
₩288,126 total
includes taxes & fees
Jul 5 - Jul 6
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 ₩108,382
₩126,192 total
includes taxes & fees
Jun 23 - Jun 24
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 ₩163,619
₩232,270 total
includes taxes & fees
Jul 1 - Jul 2
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 ₩547,931
₩616,668 total
includes taxes & fees
Jun 23 - Jun 24
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 ₩209,238
₩235,390 total
includes taxes & fees
Jun 22 - Jun 23
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 ₩112,470
₩134,175 total
includes taxes & fees
Jun 26 - Jun 27
Villa San Filippo
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (114 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is ₩120,743
₩136,303 total
includes taxes & fees
Jun 24 - Jun 25
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 ₩474,883
₩529,343 total
includes taxes & fees
Jun 24 - Jun 25
Terre di Baccio
Superior Double Room, 1 King Bed | Premium bedding, down comforters, 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 ₩220,725
₩267,200 total
includes taxes & fees
Jul 2 - Jul 3
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
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 ₩291,553
₩341,625 total
includes taxes & fees
Jul 13 - Jul 14
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 ₩200,285
₩225,542 total
includes taxes & fees
Jun 24 - Jun 25
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 ₩355,080
₩414,987 total
includes taxes & fees
Jun 30 - Jul 1
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 ₩158,580
₩198,840 total
includes taxes & fees
Jun 21 - Jun 22
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 ₩162,223
₩181,932 total
includes taxes & fees
Jul 5 - Jul 6
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top San Casciano in Val di Pesa Hotel Reviews

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

8/10 Good
"I liked the vibe of the hotel. I didn’t like how far it was from the city center. Also we used the pool one time and there were no pool towels even after asking for some and waiting 2 hours."
Raquel 4-night trip
Posted 2 hours ago
The Social Hub Florence Lavagnini

Find out more about San Casciano in Val di Pesa

Search for Vacation rentals in San Casciano in Val di Pesa on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in San Casciano in Val di Pesa using one of the methods below:

  • View our selection of featured Vacation rentals in San Casciano in Val di Pesa
  • Use the map to find apartments and other Vacation homes in the San Casciano in Val di Pesa neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in San Casciano in Val di Pesa while they last

Look no further and take a look at our great range of rental properties in San Casciano in Val di Pesa!

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 28 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. Pitti Palace and Uffizi Gallery 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.