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
25 Sep - 27 Sep
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 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, (104 reviews)
"This is an excellent property. Very historic, rustic and with great views across the Tuscan landscapes. Lorenzo and his mother were super duper hosts who took great care of us. The property dates back to 1380 and the rooms are decorated with choicest artifacts that adds greatly to the experience. The location is fantastic too with the local market and restaurants in easy walking reach. The breakfast service is fabulous with many choices and Lorenzo himself is great chef as well! Highly recommend...
United States
Nilesh
The price is ฿8,282
฿9,263 total
includes taxes & fees
3 Oct - 4 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, (84 reviews)
"Very pretty B&B! The rooms are super cozy and feels welcoming! The scenery around is just amazing! The pool was very refreshing and the host very nice! The trail to reach the B&B is narrow make sure you have a small car ;)"
Canada
Alexia
The price is ฿3,965
฿4,514 total
includes taxes & fees
5 Oct - 6 Oct
B&B La Fonte del Machiavelli

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, (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 ฿3,783
฿4,314 total
includes taxes & fees
24 Sept - 25 Sept
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
A desk with a computer monitor displaying a cityscape, a lamp, a vase with flowers, glasses, a wine bottle, and books.

4. San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
9.8 out of 10, Exceptional, (446 reviews)
"Clean, friendly staff. Great location. "
United States
Jeannette
The price is ฿7,196
฿8,375 total
includes taxes & fees
13 Sept - 14 Sept
San Giuliano Inn - Adults Only
A modern bedroom with a wooden ceiling, a large bed, bedside tables with lamps, a desk with a chair, and a mirror on the wall.

5. Sette Angeli Rooms

Sette Angeli Rooms
Historic Centre of Florence
8.8 out of 10, Excellent, (687 reviews)
"Good clean rooms and very close to the city center as well as the train station"
United Kingdom
VISHAL
The price is ฿6,695
฿7,824 total
includes taxes & fees
13 Sept - 14 Sept
Sette Angeli Rooms
A modern kitchen with a wooden countertop, a laptop, and a wine bottle.

6. Maison Ginori Guelfa

Maison Ginori Guelfa
Historic Centre of Florence
10.0 out of 10, Exceptional, (38 reviews)
"This was an incredible stay. The host was a phenomenal communicator and the property is as beautiful as pictured. If you want to be downtown in the heart of Florence, this is the perfect place to be and it is also far enough from the standard noise. I had peaceful nights and peaceful days, if I chose a late morning. It was literally near everything and I walked to every place I wanted to see. It was safe and easy to get to. I would absolutely stay at this property again and couldn’t have asked...
United States
Joyce
The price is ฿8,037
฿9,300 total
includes taxes & fees
24 Sept - 25 Sept
Maison Ginori Guelfa
A garden with a stone pathway, wooden benches, and various potted plants.

7. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (85 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is ฿5,170
฿5,878 total
includes taxes & fees
11 Oct - 12 Oct
Antico Borgo il Cardino
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

8. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (49 reviews)
"New facilities, its great, nice, friendly"
United Kingdom
tomaz
The price is ฿4,752
฿5,380 total
includes taxes & fees
5 Oct - 6 Oct
Guild Living Siena Senior Resort & Residence
A table with two wine glasses, a bottle, and a book.

9. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (97 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 ฿2,263
฿2,642 total
includes taxes & fees
7 Oct - 8 Oct
Domus il Palio B&B
A stone building with a garden in front.

10. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (27 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is ฿7,896
฿8,992 total
includes taxes & fees
16 Sept - 17 Sept
Borgo Argenina
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

11. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (89 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is ฿1,722
฿2,008 total
includes taxes & fees
13 Sept - 14 Sept
Camping Boschetto Di Piemma
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

12. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (39 reviews)
"Great spot"
Canada
Philippe
The price is ฿5,296
฿5,825 total
includes taxes & fees
21 Sept - 22 Sept
Villa di Sotto
A table with breakfast items and a view of rolling hills.

13. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (117 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is ฿2,643
฿2,984 total
includes taxes & fees
9 Oct - 10 Oct
Chianti Village Morrocco
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

14. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is ฿10,016
฿11,171 total
includes taxes & fees
25 Sept - 26 Sept
Terre di Baccio
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

15. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (264 reviews)
"Delightful location, comfortable bed, excellent food."
Canada
Rupert
The price is ฿6,119
฿6,846 total
includes taxes & fees
5 Oct - 6 Oct
Relais Villa Olmo
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 Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

8/10 Good
"Very conveniently located, room was a little smaller than expected but overall great experience!"
Brandon 3-night trip
Posted 8 hours ago
The Social Hub Florence Lavagnini

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 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 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. Monastery 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.