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 Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for San Casciano in Val di Pesa vacation 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 ￥34,822
￥39,013 total
includes taxes & fees
Oct 28 - Oct 29
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, (88 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is ￥18,343
￥20,885 total
includes taxes & fees
Oct 11 - Oct 12
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 ￥15,047
￥17,260 total
includes taxes & fees
Oct 22 - Oct 23
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.
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 ￥80,132
￥91,703 total
includes taxes & fees
Oct 9 - Oct 10
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 ￥246,259
￥246,971 total
includes taxes & fees
Oct 9 - Oct 10
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 ￥324,437
￥491,711 total
includes taxes & fees
Oct 9 - Oct 10
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 ￥87,951
￥99,522 total
includes taxes & fees
Oct 15 - Oct 16
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, (269 reviews)
"Very friendly and clean."
United States
Mohamed
The price is ￥21,657
￥24,356 total
includes taxes & fees
Oct 21 - Oct 22
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
8.6 out of 10, Excellent, (115 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is ￥6,994
￥8,224 total
includes taxes & fees
Oct 11 - Oct 12
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, (850 reviews)
"Beautiful rooms and great location"
Canada
Taylor
The price is ￥41,297
￥47,919 total
includes taxes & fees
Nov 5 - Nov 6
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 ￥11,990
￥15,313 total
includes taxes & fees
Nov 1 - Nov 2
I Parigi Corbinelli
A modern bedroom with a large bed, a desk with chairs, and a bathroom visible through an open door.

13. Palazzo Mannaioni Suites

Palazzo Mannaioni Suites
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (1,187 reviews)
"Great location"
United States
Diana
The price is ￥18,801
￥23,174 total
includes taxes & fees
Nov 2 - Nov 3
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, (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 ￥23,585
￥31,641 total
includes taxes & fees
Nov 5 - Nov 6
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, (883 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 ￥21,876
￥26,201 total
includes taxes & fees
Nov 8 - Nov 9
Relais Piazza Signoria
Room

16. La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.2 out of 10, Wonderful, (341 reviews)
"Great location easy to park car with car service they offer"
United States
Joanna
The price is ￥19,405
￥23,823 total
includes taxes & fees
Nov 8 - Nov 9
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 ￥25,375
￥30,050 total
includes taxes & fees
Nov 3 - Nov 4
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, (136 reviews)
"Book this for our honeymoon and will definitely come back"
Canada
Kerby
The price is ￥25,318
￥29,987 total
includes taxes & fees
Nov 8 - Nov 9
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, (698 reviews)
"Would stay here every time. Best rooftop in the city as well."
United States
Matthew
The price is ￥21,585
￥26,236 total
includes taxes & fees
Nov 3 - Nov 4
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, (311 reviews)
"It was a wonderful place to stay. I would highly recommend it to anyone."
United States
Salvatore
The price is ￥16,646
￥25,789 total
includes taxes & fees
Nov 1 - Nov 2
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

Hotel La Fortezza

Hotel La Fortezza

10/10 Excellent
"We only stayed here one night before traveling to a wedding about an hour away, but the stay was wonderful. The room with clean and well kept and the staff was friendly, knowledgeable, and extremely helpful! It is a bit of a walk from some of the city’s attractions, but there is a tram stop just a 2 minute walk away and the area is lovely and very walkable. Have already recommended to friends who need a place to stay on their return travel home."
Colleen 1-night trip
Posted 6 hours ago
Hotel La Fortezza

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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Frequently asked questions

Are there vacation rentals in San Casciano in Val di Pesa?

Yes, you can find vacation rentals near popular local attractions in San Casciano in Val di Pesa, or you can choose a more remote option if you want a relaxing place to 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 coffeehouses during your trip.

What's the top vacation rental in San Casciano in Val di Pesa?

Villa La Stella - Casa per Ferie: This vacation home near 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 vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in San Casciano in Val di Pesa?

Choose from 25 Expedia vacation rentals in San Casciano in Val di Pesa for a memorable vacation.

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 vacation rentals like in San Casciano in Val di Pesa?

Vacation rentals are private accommodations you can book for a short or long stay in San Casciano in Val di Pesa. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips or small group gatherings.