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

San Casciano in Val di Pesa Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 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 HK$1,931
HK$2,159 total
includes taxes & fees
13 Oct - 14 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 HK$915
HK$1,042 total
includes taxes & fees
6 Oct - 7 Oct
B&B La Fonte del Machiavelli
In-room dining

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 HK$873
HK$995 total
includes taxes & fees
19 Oct - 20 Oct
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
A garden with various plants and flowers, a pathway, and a swing set.

4. Apartment House with garden Tuscany Chianti , Florence 15km.

Apartment House with garden Tuscany Chianti , Florence 15km.
Toscana
9.8 out of 10, Exceptional, (75 reviews)
"Great property, well equipped, nice views, well maintained, very friendly and helpful host. We did really enjoy our stay :-)"
Germany
Robert M.
The price is HK$1,237
HK$1,528 total
includes taxes & fees
6 Oct - 7 Oct
Apartment House with garden Tuscany Chianti , Florence 15km.
Pool

5. Apartment 'Mini in Chianti' with Shared Pool, Wi-Fi and Air Conditioning

Apartment 'Mini in Chianti' with Shared Pool, Wi-Fi and Air Conditioning
San Casciano in Val di Pesa
The price is HK$3,975
HK$4,548 total
includes taxes & fees
6 Oct - 7 Oct
Apartment 'Mini in Chianti' with Shared Pool, Wi-Fi and Air Conditioning
An outdoor patio with a round table, chairs, a sofa, and a potted plant.

6. Molino In Chianti - Villa with Private Pool

Molino In Chianti - Villa with Private Pool
Mercatale Val Di Pesa
The price is HK$12,214
HK$12,250 total
includes taxes & fees
7 Oct - 8 Oct
Molino In Chianti - Villa with Private Pool
Pool

7. Portion of Villa Il Conventino with Pool and Wi-Fi

Portion of Villa Il Conventino with Pool and Wi-Fi
San Casciano in Val di Pesa
The price is HK$16,092
HK$24,389 total
includes taxes & fees
6 Oct - 7 Oct
Portion of Villa Il Conventino with Pool and Wi-Fi
Pool

8. Cottage in Chianti Barn with Shared Pool, Wi-Fi, and Air Conditioning

Cottage in Chianti Barn with Shared Pool, Wi-Fi, and Air Conditioning
San Casciano in Val di Pesa
The price is HK$4,362
HK$4,936 total
includes taxes & fees
15 Oct - 16 Oct
Cottage in Chianti Barn with Shared Pool, Wi-Fi, and Air Conditioning
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 HK$1,023
HK$1,152 total
includes taxes & fees
2 Nov - 3 Nov
Relais Villa Olmo
A water park with a pool, slides, and a wooden deck area.

10. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very good, (108 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is HK$379
HK$444 total
includes taxes & fees
6 Oct - 7 Oct
hu Firenze Certosa camping in town
A terrace with outdoor seating, a view of the city, and a clock tower in the background.

11. Palazzo Alfieri Residenza d’epoca

Palazzo Alfieri Residenza d’epoca
Historic Centre of Florence
9.2 out of 10, Wonderful, (842 reviews)
"Beautiful rooms and great location"
Canada
Taylor
The price is HK$2,031
HK$2,358 total
includes taxes & fees
5 Nov - 6 Nov
Palazzo Alfieri Residenza d’epoca
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

12. 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 HK$598
HK$764 total
includes taxes & fees
1 Nov - 2 Nov
I Parigi Corbinelli
A conference room with a stone wall, a wooden ceiling, and a table with chairs.

13. Palazzo Mannaioni Suites

Palazzo Mannaioni Suites
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (1,185 reviews)
"Great location"
United States
Diana
The price is HK$932
HK$1,149 total
includes taxes & fees
3 Nov - 4 Nov
Palazzo Mannaioni Suites
A glass-top table with a sofa, a candle, a pitcher, and two glasses of drink.

14. Tornabuoni Suites Collection

Tornabuoni Suites Collection
Historic Centre of Florence
9.6 out of 10, Exceptional, (336 reviews)
"Great location, very clean room, and friendly, helpful staff. We had a very comfortable stay and would happily stay here again."
United States
HYEUNJOO
The price is HK$1,170
HK$1,569 total
includes taxes & fees
3 Nov - 4 Nov
Tornabuoni Suites Collection
A balcony with a table, wine glasses, and a bottle, overlooking a historic building with a clock tower and another tower.

15. Relais Piazza Signoria

Relais Piazza Signoria
Historic Centre of Florence
9.6 out of 10, Exceptional, (881 reviews)
"The people were all extremely nice and helpful, location was amazing, exactly what we were after having never been to Florence !!"
United States
David
The price is HK$1,023
HK$1,232 total
includes taxes & fees
1 Nov - 2 Nov
Relais Piazza Signoria
Room

16. La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.2 out of 10, Wonderful, (338 reviews)
"Great location easy to park car with car service they offer"
United States
Joanna
The price is HK$867
HK$1,078 total
includes taxes & fees
4 Nov - 5 Nov
La Torre Del Cestello
A modern bedroom with a wooden ceiling, a bed with a white headboard, a beige sofa, and a glass-enclosed shower area with marble walls.

17. Residenza La Musa Amarcord

Residenza La Musa Amarcord
Historic Centre of Florence
9.8 out of 10, Exceptional, (178 reviews)
"Very good place. Walkable distance to every where. Clean and large room. Very comfortable."
United States
Yujia
The price is HK$984
HK$1,188 total
includes taxes & fees
5 Nov - 6 Nov
Residenza La Musa Amarcord
Reception

18. Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione
Historic Centre of Florence
9.8 out of 10, Exceptional, (131 reviews)
"Book this for our honeymoon and will definitely come back"
Canada
Kerby
The price is HK$1,534
HK$1,793 total
includes taxes & fees
1 Nov - 2 Nov
Teatro Luxury Apartments Firenze - Starhotels Collezione
A terrace with a table set for dining, overlooking a cityscape with historic buildings and a prominent dome.

19. Palazzo Graziani

Palazzo Graziani
Historic Centre of Florence
9.2 out of 10, Wonderful, (695 reviews)
"Would stay here every time. Best rooftop in the city as well."
United States
Matthew
The price is HK$1,097
HK$1,330 total
includes taxes & fees
5 Nov - 6 Nov
Palazzo Graziani
A wooden door with a sign, a large potted plant, and a view of a historic building.

20. La Casa del Garbo - Luxury Rooms & Suite

La Casa del Garbo - Luxury Rooms & Suite
Historic Centre of Florence
9.6 out of 10, Exceptional, (309 reviews)
"It was a wonderful place to stay. I would highly recommend it to anyone."
United States
Salvatore
The price is HK$772
HK$1,220 total
includes taxes & fees
1 Nov - 2 Nov
La Casa del Garbo - Luxury Rooms & Suite
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
"Staff was friendly and accommodating! Rooms were very clean and SPACIOUS! Would definitely return!"
Suzette 1-night trip
Posted 1 hour 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 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. 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.