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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 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 6.204.545 ₫
6.943.397 ₫ total
includes taxes & fees
23 Oct - 24 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, (85 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is 3.067.561 ₫
3.492.714 ₫ total
includes taxes & fees
4 Oct - 5 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, (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 2.857.918 ₫
3.262.107 ₫ total
includes taxes & fees
8 Oct - 9 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

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (266 reviews)
"Very friendly and clean."
United States
Mohamed
The price is 4.322.832 ₫
4.843.913 ₫ total
includes taxes & fees
11 Oct - 12 Oct
Relais Villa Olmo
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
8.4 out of 10, Very good, (107 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is 1.271.423 ₫
1.487.364 ₫ total
includes taxes & fees
7 Oct - 8 Oct
hu Firenze Certosa camping in town
A swimming pool with lounge chairs and a flag.

6. Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.2 out of 10, Very good, (263 reviews)
"Great location easy access to Firenze"
Canada
Donnie
The price is 2.305.515 ₫
2.950.456 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Fattoria il Milione Agriturismo
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

7. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"Amazing property. Air conditioning works. Dinner and breakfast is first class. Free parking"
United States
SYDNEY
The price is 8.233.979 ₫
9.175.774 ₫ total
includes taxes & fees
25 Sept - 26 Sept
Terre di Baccio
A modern bedroom with a large bed, a desk with chairs, and a bathroom visible through an open door.

8. Palazzo Mannaioni Suites

Palazzo Mannaioni Suites
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (1,175 reviews)
"Great location"
United States
Diana
The price is 6.923.566 ₫
8.030.283 ₫ total
includes taxes & fees
9 Oct - 10 Oct
Palazzo Mannaioni Suites

9. La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.2 out of 10, Wonderful, (324 reviews)
"Clean room friendly staff definitely be back"
United States
IVAN
The price is 5.630.589 ₫
6.608.038 ₫ total
includes taxes & fees
18 Oct - 19 Oct
La Torre Del Cestello
A terrace with outdoor seating, a view of the city, and a clock tower in the background.

10. Il Rivalta - Place of Charme

Il Rivalta - Place of Charme
4.0 star property
Historic Centre of Florence
9.4 out of 10, Exceptional, (626 reviews)
"Il Rivata was above and beyond my expectations. It was an incredible value in a wonderful location"
United States
Brian
The price is 9.282.284 ₫
10.624.902 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Il Rivalta - Place of Charme
A hotel room with a bed, a bedside table, a heater, a mirror, and a bathroom with a sink.

11. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,738 reviews)
"Love this place, came back twice. Literally had all you need . The shuttle downtown is amazing, exploring with families can be chaotic this helped. The pool gets a bit crowded during peak season but still worth a visit."
United States
Ama
The price is 1.574.089 ₫
1.938.752 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Hu Firenze Camping In Town
A room with a dining table, a vase of flowers, a lamp, and a view of a historic building through a window.

12. Mamo Florence - Le Farine Della Signoria Apartments

Mamo Florence - Le Farine Della Signoria Apartments
Historic Centre of Florence
8.6 out of 10, Excellent, (10 reviews)
"Amazing property with excellent views. "
United States
Karl
The price is 4.015.895 ₫
6.696.628 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Mamo Florence - Le Farine Della Signoria Apartments
A dining area with a table set for two, featuring a view of greenery through a window.

13. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (38 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is 4.473.526 ₫
5.039.275 ₫ total
includes taxes & fees
26 Sept - 27 Sept
La Locanda di Pietracupa
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, (306 reviews)
"Location was incredible. Staff was incredibly helpful and accommodating. We ended up missing check in due to a late train and they were very kind to set up late check in for us last minute. Rooms were so cute and spacious. Had read some reviews about the noise from the plaza being loud, but we couldn't hear a thing. Will be staying here again when visiting Florence."
United States
Kristin
The price is 4.169.275 ₫
5.829.371 ₫ total
includes taxes & fees
21 Oct - 22 Oct
La Casa del Garbo - Luxury Rooms & Suite
A terrace with a table set for breakfast, a chair, and a large umbrella.

15. Villa La Stella - Casa per Ferie

Villa La Stella - Casa per Ferie
Le Cure
8.6 out of 10, Excellent, (254 reviews)
"It’s was great"
United States
Rocio
The price is 3.612.779 ₫
4.210.851 ₫ total
includes taxes & fees
11 Oct - 12 Oct
Villa La Stella - Casa per Ferie
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

c-hotels Ambasciatori

c-hotels Ambasciatori

10/10 Excellent
"Hotel was nice, the AC was ok could't turn it down. it was warm in the room! But other than that it was nice."
Rula 4-night trip
Posted less than an hour ago
c-hotels Ambasciatori

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 24 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.