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

Search Holiday Rentals in San Casciano in Val di Pesa

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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, (108 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is 4.123.111 ₫
4.651.017 ₫ total
includes taxes & fees
23 Nov - 24 Nov
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, (93 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is 2.987.506 ₫
3.401.564 ₫ total
includes taxes & fees
2 Nov - 3 Nov
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, (29 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 2.640.798 ₫
3.020.185 ₫ total
includes taxes & fees
5 Nov - 6 Nov
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
A stone building with a patio area featuring a table and chairs under a large umbrella.

4. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (274 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is 2.408.091 ₫
2.735.596 ₫ total
includes taxes & fees
29 Nov - 30 Nov
Relais Villa Olmo - Place of Charme
A tented room with a bed, curtains, and a view of an outdoor deck.

5. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (122 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
The price is 1.238.243 ₫
1.448.547 ₫ total
includes taxes & fees
1 Nov - 2 Nov
hu Firenze Certosa camping in town
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

6. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (173 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 1.952.885 ₫
2.494.095 ₫ total
includes taxes & fees
4 Nov - 5 Nov
I Parigi Corbinelli
A modern house with glass walls and a patio area.

7. Marignolle Relais and Charme

Marignolle Relais and Charme
Florence
9.2 out of 10, Wonderful, (94 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 3.596.118 ₫
4.302.515 ₫ total
includes taxes & fees
29 Nov - 30 Nov
Marignolle Relais and Charme
A historic building with ornate iron gates, potted plants, and a visible staircase leading to an upper floor.

8. Signoria Collection

Signoria Collection
Historic Centre of Florence
9.8 out of 10, Exceptional, (18 reviews)
"Room was always clean. Location is amazing."
Canada
Doug
The price is 3.735.954 ₫
4.455.471 ₫ total
includes taxes & fees
24 Nov - 25 Nov
Signoria Collection
A terrace with outdoor seating, a view of the city, and a clock tower in the background.

9. 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, (862 reviews)
"The staff are amazing & the location is great"
United Kingdom
Helen Jane
The price is 4.405.008 ₫
5.250.091 ₫ total
includes taxes & fees
23 Nov - 24 Nov
Palazzo Alfieri Residenza d’epoca - Place of Charme
A stone building with a wooden door, a grill outside, and a stone wall.

10. Teranga in Chianti - Parking & Garden 3 BR

Teranga in Chianti - Parking & Garden 3 BR
Tavarnelle Val di Pesa
The price is 2.620.619 ₫
10.204.690 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Teranga in Chianti - Parking & Garden 3 BR
A building with multiple windows, a balcony with balustrade, and storefronts with awnings.

11. Anchor Santa Croce

Anchor Santa Croce
Historic Centre of Florence
9.8 out of 10, Exceptional, (9 reviews)
"Amazing place to stay. Clean, close to main touristic attractions in Florence."
Canada
Adina
The price is 2.759.417 ₫
3.381.281 ₫ total
includes taxes & fees
5 Nov - 6 Nov
Anchor Santa Croce
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.

12. Residenza La Musa Amarcord

Residenza La Musa Amarcord
Historic Centre of Florence
10.0 out of 10, Exceptional, (181 reviews)
"Great location away from the crowds. Quiet. Elegant hotel with a friendly and pleasant staff."
United States
Samuel
The price is 2.645.546 ₫
3.256.886 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Residenza La Musa Amarcord
A balcony with wicker furniture, overlooking a historic square with a prominent tower and a clock.

13. Relais Piazza Signoria

Relais Piazza Signoria
Historic Centre of Florence
9.4 out of 10, Exceptional, (890 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 2.834.190 ₫
3.464.394 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Relais Piazza Signoria
A balcony with a glass table, white curtains, and a bottle of champagne.

14. Dimora Bandinelli Firenze

Dimora Bandinelli Firenze
Oltrarno
9.8 out of 10, Exceptional, (190 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
The price is 2.341.457 ₫
2.921.525 ₫ total
includes taxes & fees
3 Nov - 4 Nov
Dimora Bandinelli Firenze
A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

15. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 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 6.981.329 ₫
7.794.769 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Terre di Baccio
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top San Casciano in Val di Pesa Hotel Reviews

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

10/10 Excellent
"The property was amazing!!"
Tara 2-night trip
Posted 4 hours ago
The Social Hub Florence Lavagnini

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.