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San Casciano in Val di Pesa Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for San Casciano in Val di Pesa vacation 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 NT$4,617
NT$5,227 total
includes taxes & fees
Jan 9 - 2026/1/10
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 NT$4,314
NT$4,894 total
includes taxes & fees
Dec 30 - Dec 31
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
Chalet | In-room safe, cribs/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 NT$2,977
NT$4,385 total
includes taxes & fees
Jan 19 - 2026/1/20
Palazzo al Torrione 2
Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, sun 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, sun 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 NT$5,304
NT$6,352 total
includes taxes & fees
Jan 11 - 2026/1/12
Palazzo Alfieri Residenza d’epoca
Apartment, 2 Bedrooms | Premium bedding, down comforters, in-room safe, blackout drapes
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 NT$17,850
NT$19,783 total
includes taxes & fees
Dec 31 - 2026/1/1
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 NT$6,265
NT$7,410 total
includes taxes & fees
Jan 11 - 2026/1/12
Il Rivalta - Place of Charme
Classic Suite, 1 King Bed | Premium bedding, down comforters, 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, (231)
"Great location and great rooms"
United States
David
The price is NT$2,997
NT$3,815 total
includes taxes & fees
Jan 7 - 2026/1/8
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 NT$4,320
NT$5,270 total
includes taxes & fees
Jan 6 - 2026/1/7
Soggiorno Battistero
Lounge
Corte Guelfa

Corte Guelfa

Corte Guelfa
3.0 star property
Historic Centre of Florence
9.8 out of 10, Exceptional, (162)
"Great surrounding and vibe. Helpful staff."
Singapore
Soon Tiong
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 NT$2,927
NT$3,663 total
includes taxes & fees
Jan 7 - 2026/1/8
Numa Palazzo San Niccolò
Deluxe Penthouse, 3 Bedrooms, 2 Bathrooms | 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, (373)
"Very spacious and clean stay with premium proximity to the city"
United States
Raehmojhzn
The price is NT$5,610
NT$6,615 total
includes taxes & fees
Jan 11 - 2026/1/12
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 NT$4,251
NT$5,120 total
includes taxes & fees
Jan 28 - 2026/1/29
Relais Piazza Signoria
Deluxe Double Room (1° floor) | Egyptian cotton sheets, premium bedding, down comforters
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 NT$2,668
NT$3,379 total
includes taxes & fees
Jan 29 - 2026/1/30
Sette Angeli Rooms
Deluxe Suite, 2 Bedrooms | Premium bedding, down comforters, iron/ironing board, cribs/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 NT$3,633
NT$4,440 total
includes taxes & fees
Jan 7 - 2026/1/8
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 2 days 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! You can easily find your home rentals, villas, holiday apartments in San Casciano in Val di Pesa using one of the methods below:

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

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.