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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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 5.756.235 ₫
6.447.772 ₫ total
includes taxes & fees
21 Oct - 22 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, (90 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is 3.003.226 ₫
3.419.462 ₫ total
includes taxes & fees
13 Oct - 14 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 2.496.629 ₫
2.862.205 ₫ total
includes taxes & fees
26 Oct - 27 Oct
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

4. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.4 out of 10, Exceptional, (270 reviews)
"Very friendly and clean."
United States
Mohamed
The price is 3.516.468 ₫
3.955.050 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Relais Villa Olmo - Place of Charme
A water park with a pool, slides, and a wooden deck area.

5. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (117 reviews)
"Friendly staff!"
United States
larisa
The price is 1.244.758 ₫
1.456.169 ₫ total
includes taxes & fees
13 Oct - 14 Oct
hu Firenze Certosa camping in town
A modern bathroom with a freestanding bathtub, a vanity with a large sink, and a mirror.

6. Palazzo Alfieri Residenza d’epoca - Place of Charme

Palazzo Alfieri Residenza d’epoca - Place of Charme
Historic Centre of Florence
9.2 out of 10, Wonderful, (854 reviews)
"Beautiful rooms and great location"
Canada
Taylor
The price is 6.609.521 ₫
7.676.172 ₫ total
includes taxes & fees
12 Nov - 13 Nov
Palazzo Alfieri Residenza d’epoca - Place of Charme
Reception

7. Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione
Historic Centre of Florence
9.8 out of 10, Exceptional, (139 reviews)
"Book this for our honeymoon and will definitely come back"
Canada
Kerby
The price is 4.478.495 ₫
5.274.087 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Teatro Luxury Apartments Firenze - Starhotels Collezione
A table set with croissants, coffee cups, and a vase with flowers on a balcony overlooking a cityscape.

8. Antica Torre di Via Tornabuoni 1

Antica Torre di Via Tornabuoni 1
Historic Centre of Florence
9.8 out of 10, Exceptional, (612 reviews)
"My mom and I stayed there for a couple of nights and we loved it. Our room was spacious and very clean, welcoming gifts were a nice touch. The location was perfect, close to everything. Highly recommend this hotel!"
United States
NAZLI
The price is 8.379.896 ₫
9.565.627 ₫ total
includes taxes & fees
4 Nov - 5 Nov
Antica Torre di Via Tornabuoni 1
A glass-top table with a sofa, a candle, a pitcher, and two glasses of drink.

9. Tornabuoni Suites Collection

Tornabuoni Suites Collection
Historic Centre of Florence
9.6 out of 10, Exceptional, (337 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 3.838.101 ₫
5.149.224 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Tornabuoni Suites Collection
Room

10. La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.0 out of 10, Wonderful, (345 reviews)
"Great location easy to park car with car service they offer"
United States
Joanna
The price is 2.291.534 ₫
2.926.387 ₫ total
includes taxes & fees
9 Nov - 10 Nov
La Torre Del Cestello
A historic building with ornate iron gates, potted plants, and a visible staircase leading to an upper floor.

11. Signoria Collection

Signoria Collection
Historic Centre of Florence
9.8 out of 10, Exceptional, (17 reviews)
"Room was always clean. Location is amazing."
Canada
Doug
The price is 4.481.234 ₫
5.277.100 ₫ total
includes taxes & fees
4 Nov - 5 Nov
Signoria Collection
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 1.963.161 ₫
2.507.219 ₫ total
includes taxes & fees
1 Nov - 2 Nov
I Parigi Corbinelli
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

13. 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 7.018.065 ₫
7.835.785 ₫ total
includes taxes & fees
16 Oct - 17 Oct
Terre di Baccio
A wooden door with a sign, a large potted plant, and a view of a historic building.

14. La Casa del Garbo - Luxury Rooms & Suite

La Casa del Garbo - Luxury Rooms & Suite
Historic Centre of Florence
9.6 out of 10, Exceptional, (313 reviews)
"Great spot at an even better centrally located location. Staff were great. We really enjoyed our stay."
Canada
Thomas
The price is 2.428.758 ₫
3.888.731 ₫ total
includes taxes & fees
10 Nov - 11 Nov
La Casa del Garbo - Luxury Rooms & Suite
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, (885 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 3.201.118 ₫
3.868.972 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Relais Piazza Signoria
A terrace with outdoor seating, a view of the city, and a clock tower in the background.

16. Il Rivalta - Place of Charme

Il Rivalta - Place of Charme
4.0 star property
Historic Centre of Florence
9.4 out of 10, Exceptional, (638 reviews)
"Lovely hotel, great location."
United Kingdom
Robert
The price is 6.970.526 ₫
8.073.277 ₫ total
includes taxes & fees
6 Nov - 7 Nov
Il Rivalta - Place of Charme
A terrace with a table set for dining, overlooking a cityscape with historic buildings and a prominent dome.

17. Palazzo Graziani

Palazzo Graziani
Historic Centre of Florence
9.2 out of 10, Wonderful, (700 reviews)
"Would stay here every time. Best rooftop in the city as well."
United States
Matthew
The price is 3.489.726 ₫
4.244.397 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Palazzo Graziani
A modern house with glass walls and a patio area.

18. Marignolle Relais and Charme

Marignolle Relais and Charme
Florence
9.2 out of 10, Wonderful, (93 reviews)
"The Marignolle Relais & Charme is absolutely gorgeous. The rooms are beautifully decorated and everything is so clean. The grounds are well maintained and the pool area is stunning. We loved our two day stay and heartily recommend it. Stay here you’ll love it!!!"
Canada
Honey
The price is 4.657.532 ₫
5.471.027 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Marignolle Relais and Charme
A hallway with a mirror, a vase, and a painting on the wall.

19. Residenza Della Signoria

Residenza Della Signoria
Historic Centre of Florence
9.6 out of 10, Exceptional, (355 reviews)
"This was in a great location!!! We loved staying here! Comfy bed and pillows plus huge bath towels."
United States
Kevin
The price is 3.325.463 ₫
4.005.752 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Residenza Della Signoria
A table with breakfast items and a view of rolling hills.

20. 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 2.227.050 ₫
2.507.712 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Chianti Village Morrocco
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

Plus Florence - Hostel

Plus Florence - Hostel

10/10 Excellent
"Facilities are very nice. Easy access to everything. Staff is friendly and helpful. Would stay here again anytime!"
Noah 4-night trip
Posted 2 hours ago
Plus Florence - Hostel

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.