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San Casciano in Val di Pesa Vacation Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

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

Exterior detail
Villa il Fedino

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is RM595
RM673 total
includes taxes & fees
9 Jan - 10 Jan 2026
Villa il Fedino
Terrace/patio
B&B La Fonte del Machiavelli

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)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is RM494
RM563 total
includes taxes & fees
29 Dec - 30 Dec
B&B La Fonte del Machiavelli
Food and drink
San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
10.0 out of 10, Exceptional, (406)
"Great inn. "
United States
Carol
San Giuliano Inn - Adults Only
In-room safe, cots/infant beds, bed sheets
Hu Firenze Camping In Town

Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1613)
"It was a grt place to stay"
United States
Sunitha
Hu Firenze Camping In Town
Balcony
Palazzo al Torrione 2

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (107)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is RM384
RM565 total
includes taxes & fees
19 Jan - 20 Jan 2026
Palazzo al Torrione 2
Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, pool loungers
Tenuta Sant'Ilario

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (33)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario
Breakfast, lunch, dinner served; Regional cuisine
La Locanda di Pietracupa

La Locanda di Pietracupa

La Locanda di Pietracupa
Barberino Tavarnelle
9.4 out of 10, Exceptional, (35)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa
Outdoor pool, pool umbrellas, pool loungers
Chianti Village Morrocco

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (108)
"Spacious room in large resort style complex, set up as fully self contained with kitchen and dining furniture. Peaceful location with lovely views. Very pleasant staff and exceptional breakfast. "
France
Richard
Chianti Village Morrocco
Terrace/patio
Palazzo Alfieri Residenza d’epoca

Palazzo Alfieri Residenza d’epoca

Palazzo Alfieri Residenza d’epoca
Historic Centre of Florence
9.2 out of 10, Wonderful, (727)
"This was such a lovely hotel! It was in a great location with an incredible view. The staff was great and the breakfast was absolutely fantastic! I would highly recommend this hotel "
United States
Christine
The price is RM713
RM851 total
includes taxes & fees
9 Jan - 10 Jan 2026
Palazzo Alfieri Residenza d’epoca
Premium bedding, down duvets, in-room safe, blackout curtains
Terre di Baccio

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (71)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is RM2,300
RM2,549 total
includes taxes & fees
31 Dec - 1 Jan 2026
Terre di Baccio
Terrace/patio
Il Rivalta - Place of Charme

Il Rivalta - Place of Charme

Il Rivalta - Place of Charme
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (446)
"A really nice place to stay and close to everything you need. Would definitely go back and stay. "
United States
Tejwant
The price is RM840
RM991 total
includes taxes & fees
10 Jan - 11 Jan 2026
Il Rivalta - Place of Charme
Premium bedding, down duvets, in-room safe, desk
La Torre Del Cestello

La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.0 out of 10, Wonderful, (230)
"Great location and great rooms"
United States
David
The price is RM407
RM514 total
includes taxes & fees
11 Jan - 12 Jan 2026
La Torre Del Cestello
City view from property
Soggiorno Battistero

Soggiorno Battistero

Soggiorno Battistero
Historic Centre of Florence
8.8 out of 10, Excellent, (383)
"We were worried about the noise of the busy tourist spot, but the windows were fantastic and was able to sleep soundly. Great location, highly recommend."
Canada
Jason
The price is RM542
RM663 total
includes taxes & fees
7 Jan - 8 Jan 2026
Soggiorno Battistero
Lounge
Corte Guelfa

Corte Guelfa

Corte Guelfa
3.0 star property
Historic Centre of Florence
9.8 out of 10, Exceptional, (161)
"Great location, attentive staff, clean rooms"
United States
Dennis
Corte Guelfa
Terrace/patio
Numa Palazzo San Niccolò

Numa Palazzo San Niccolò

Numa Palazzo San Niccolò
Historic Centre of Florence
9.4 out of 10, Exceptional, (175)
"Clean, amenities, breakfast! "
United States
Laury
The price is RM372
RM466 total
includes taxes & fees
7 Jan - 8 Jan 2026
Numa Palazzo San Niccolò
Terrace/patio
Serristori Palace Residence

Serristori Palace Residence

Serristori Palace Residence
Historic Centre of Florence
9.6 out of 10, Exceptional, (171)
"Perfect stay. Apartment was immaculate as were all the public areas of the building. Helpful friendly staff and ideally placed to explore Florence’s "
United Kingdom
Michele
Serristori Palace Residence
Exterior
Numa Florence Palazzo Belfiore

Numa Florence Palazzo Belfiore

Numa Florence Palazzo Belfiore
Historic Centre of Florence
9.6 out of 10, Exceptional, (372)
"Great property, plenty of space for my family. The location is great, we were able to walk everywhere including the train station. "
United States
Loren
The price is RM723
RM852 total
includes taxes & fees
11 Jan - 12 Jan 2026
Numa Florence Palazzo Belfiore
Reception
Relais Piazza Signoria

Relais Piazza Signoria

Relais Piazza Signoria
Historic Centre of Florence
9.6 out of 10, Exceptional, (801)
"The location was perfect! The room was spacious and comfortable. It was a fantastic stay!"
United States
Kenzie
The price is RM548
RM660 total
includes taxes & fees
20 Jan - 21 Jan 2026
Relais Piazza Signoria
Egyptian cotton sheets, premium bedding, down duvets
Sette Angeli Rooms

Sette Angeli Rooms

Sette Angeli Rooms
Historic Centre of Florence
8.8 out of 10, Excellent, (636)
"I loved this place and the stuff was very kind <3 "
United Kingdom
romina
The price is RM357
RM450 total
includes taxes & fees
18 Jan - 19 Jan 2026
Sette Angeli Rooms
Premium bedding, down duvets, iron/ironing board, cots/infant beds
Palazzo Branchi

Palazzo Branchi

Palazzo Branchi
Historic Centre of Florence
9.0 out of 10, Wonderful, (287)
"WHAT A GREAT STAY. The location is perfect if you want to stay in the heart of Florence. Easy to reach all of the main attractions. The room was so pretty and spacious. Our host was very helpful, greeted us at the door, and had with great tips! Will stay here again. "
United States
Jeannette
The price is RM468
RM572 total
includes taxes & fees
7 Jan - 8 Jan 2026
Palazzo Branchi
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

Grand Hotel Cavour

Grand Hotel Cavour

10/10 Excellent
"This is a great location, and the property is super nice. I will definitely stay here again."
Juan 1-night trip
Posted 18 hours ago
Grand Hotel Cavour

Find out more about San Casciano in Val di Pesa

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

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

What are some of the best holiday rentals that San Casciano in Val di Pesa has to offer?

Villa La Stella - Casa per Ferie: This holiday home rental outside of 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 holiday rental also comes with free parking to give you added peace of mind.

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

Choose from 18 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. Monastary of Sorelle Clarisse and Antinori nel Chianti Classico are other places to visit while you're in town.

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.