A vineyard with rows of grapevines on rolling hills, a small house, and a mountain range in the background.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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

An arched entrance with a lantern above, flanked by two potted plants.

1. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (105 reviews)
"Tha parking was easy on the property. It was within walking distance to the villages with shops, restaurants and cafes. The best part was the staff. The owners were incredibly helpful, friendly and made you feel like family. Breakfast outside was lovely overlooking the hills of Tuscany. We met many people and had lovely conversations with other travelers during breakfast. A gem in Tuscany."
United States
Lori
The price is 6.386.777 ₫
7.143.669 ₫ total
includes taxes & fees
6 Oct - 7 Oct
Villa il Fedino
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

2. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (87 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is 3.051.633 ₫
3.474.578 ₫ total
includes taxes & fees
28 Oct - 29 Oct
B&B La Fonte del Machiavelli
Exterior

3. 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, (28 reviews)
"Me and my girlfriend really did enjoy this property. Both host were very friendly and welcoming to us. We both did enjoy the feel at Home environment. We would definitely come back here on a future trip. Big shout out to the host for the wonderful cook meals. Great to know a bit about them as well."
United States
Erick
The price is 2.917.337 ₫
3.327.197 ₫ total
includes taxes & fees
13 Oct - 14 Oct
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
A modern bedroom with a large bed, a desk with chairs, and a bathroom visible through an open door.

4. Palazzo Mannaioni Suites

Palazzo Mannaioni Suites
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (1,181 reviews)
"Great location"
United States
Diana
The price is 6.234.512 ₫
7.270.113 ₫ total
includes taxes & fees
9 Oct - 10 Oct
Palazzo Mannaioni Suites
A terrace with outdoor seating, a view of the city, and a clock tower in the background.

5. Il Rivalta - Place of Charme

Il Rivalta - Place of Charme
4.0 star property
Historic Centre of Florence
9.4 out of 10, Exceptional, (627 reviews)
"Il Rivata was above and beyond my expectations. It was an incredible value in a wonderful location"
United States
Brian
The price is 8.188.262 ₫
9.419.326 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Il Rivalta - Place of Charme
A balcony with a table, wine glasses, and a bottle, overlooking a historic building with a clock tower and another tower.

6. Relais Piazza Signoria

Relais Piazza Signoria
Historic Centre of Florence
9.6 out of 10, Exceptional, (877 reviews)
"great staff. Very accessible and close to very good restaurants and gelaterias."
Canada
Melika
The price is 5.978.096 ₫
6.929.253 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Relais Piazza Signoria
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

7. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (170 reviews)
"Beautiful setting, stunning views, incredible pool and gardens and so easy to jump on the bus into the city."
United Kingdom
Jacqui
The price is 2.758.248 ₫
3.387.420 ₫ total
includes taxes & fees
6 Oct - 7 Oct
I Parigi Corbinelli
A wooden door with a sign, a large potted plant, and a view of a historic building.

8. La Casa del Garbo - Luxury Rooms & Suite

La Casa del Garbo - Luxury Rooms & Suite
Historic Centre of Florence
9.6 out of 10, Exceptional, (308 reviews)
"It was a wonderful place to stay. I would highly recommend it to anyone."
United States
Salvatore
The price is 4.043.168 ₫
5.684.199 ₫ total
includes taxes & fees
27 Oct - 28 Oct
La Casa del Garbo - Luxury Rooms & Suite
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

9. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (268 reviews)
"Very friendly and clean."
United States
Mohamed
The price is 3.627.841 ₫
4.078.962 ₫ total
includes taxes & fees
21 Oct - 22 Oct
Relais Villa Olmo
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

10. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (80 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is 7.131.184 ₫
7.962.085 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Terre di Baccio
A terrace with a table set for dining, overlooking a cityscape with historic buildings and a prominent dome.

11. Palazzo Graziani

Palazzo Graziani
Historic Centre of Florence
9.2 out of 10, Wonderful, (692 reviews)
"Would stay here every time. Best rooftop in the city as well."
United States
Matthew
The price is 5.410.379 ₫
6.363.655 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Palazzo Graziani
An outdoor dining area with a table set for two, surrounded by chairs, a potted plant, and a view of a building with a staircase.

12. Serristori Palace Residence

Serristori Palace Residence
Historic Centre of Florence
9.6 out of 10, Exceptional, (236 reviews)
"Great location and great property!"
Canada
Imamah
The price is 5.817.945 ₫
6.753.086 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Serristori Palace Residence
A courtyard with outdoor seating, a building with shutters, and lush greenery.

13. Numa Florence Palazzo San Niccolò

Numa Florence Palazzo San Niccolò
Historic Centre of Florence
9.4 out of 10, Exceptional, (210 reviews)
"Very nice place, backing onto the mountain and quiet. Clean and spacious. Comfortable beds. Only complaint which is not a great one is that it was too digital - the front door & room key were down for most of a day (creating an hassle because of the lack of onsite staff) and the wifi was down for 2 days, leading to inconvenience. Otherwise good place in a good location."
Canada
Dante
The price is 5.607.247 ₫
6.521.319 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Numa Florence Palazzo San Niccolò
A crowded square with a historic building featuring intricate architectural details.

14. Soggiorno Battistero

Soggiorno Battistero
Historic Centre of Florence
8.8 out of 10, Excellent, (431 reviews)
"The most central location you can stay in Florence! Good breakfast included. Staff gave us great recommendation for restaurants. They also let us store our bags after our check out time. Definitely recommend."
United States
Eugen
The price is 6.807.349 ₫
7.900.322 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Soggiorno Battistero
A terrace with outdoor seating, a view of the city, and a clock tower in the background.

15. Palazzo Alfieri Residenza d’epoca

Palazzo Alfieri Residenza d’epoca
Historic Centre of Florence
9.2 out of 10, Wonderful, (840 reviews)
"Beautiful rooms and great location"
Canada
Taylor
The price is 7.953.195 ₫
9.160.752 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Palazzo Alfieri Residenza d’epoca
A table with breakfast items and a view of rolling hills.

16. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."
United States
Winonah
The price is 1.888.069 ₫
2.135.767 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Chianti Village Morrocco
A hallway with a white door at the end, flanked by two large windows with black frames and wall-mounted lamps.

17. Nove Guest House

Nove Guest House
Historic Centre of Florence
10.0 out of 10, Exceptional, (92 reviews)
"Fulvio was so welcoming and helpful with showing us things to do in Florence! The room was very clean, spacious, and in walking distance to anything you would want to see in town. Definitely recommend!!"
United States
Foster
The price is 6.213.164 ₫
7.187.828 ₫ total
includes taxes & fees
9 Oct - 10 Oct
Nove Guest House
A balcony with a glass table, white curtains, and a bottle of champagne.

18. Dimora Bandinelli Firenze

Dimora Bandinelli Firenze
Oltrarno
9.8 out of 10, Exceptional, (189 reviews)
"We had a wonderful experience with hotel owners. Great hospitality, beautiful room, perfect location. Breakfast included, good selection of breakfast options. Highly recommend this place if you’re visiting Florence"
United States
Marat
Dimora Bandinelli Firenze
A building with a large wooden door and a number '25' sign.

19. Residenza D'Epoca Sant Anna

Residenza D'Epoca Sant Anna
Historic Centre of Florence
7.8 out of 10, Good, (291 reviews)
"This was a good spot to pick. Walking distance from the train station. Walking distance to all the big sites and the river. The staff was very friendly and helpful."
Canada
Zaki
The price is 4.748.800 ₫
5.637.121 ₫ total
includes taxes & fees
6 Oct - 7 Oct
Residenza D'Epoca Sant Anna
A hotel entrance with a checkered floor, potted plants, and a sign reading "CORTE GUELFA".

20. Corte Guelfa

Corte Guelfa
3.0 star property
Historic Centre of Florence
9.6 out of 10, Exceptional, (219 reviews)
"It was a pleasantly surprised how clean, well maintained the property and room was. Staff were so friendly and helpful. We should have stayed longer here!"
Italy
Kevin
The price is 5.766.686 ₫
6.696.701 ₫ total
includes taxes & fees
23 Oct - 24 Oct
Corte Guelfa
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

Palazzo Montebello

Palazzo Montebello

10/10 Excellent
"."
James 2-night trip
Posted 2 hours ago
Palazzo Montebello

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 25 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. Piazza di Santa Maria Novella and Piazza del Duomo 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.