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

Holiday Homes in San Casciano in Val di Pesa

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for San Casciano in Val di Pesa holiday homes

Outdoor dining

1. House with views of the Chianti

House with views of the Chianti
impruneta
10.0 out of 10, 4, (4 reviews)
"My wife and I stayed here for our honeymoon and have already talked about returning here for an anniversary. This house was clean, charming and located in a beautiful area. The views from the property are stunning."
United States
Chase B.
The price is NZ$459
includes taxes & fees
17 Sept - 18 Sept
House with views of the Chianti
Outdoor dining

2. Wonderful Tuscan farmhouse with large spaces and panoramic views

Wonderful Tuscan farmhouse with large spaces and panoramic views
impruneta
9.6 out of 10, 27, (27 reviews)
"Lovely area. Charming house. "
United States
Christine F.
The price is NZ$499
includes taxes & fees
28 Sept - 29 Sept
Wonderful Tuscan farmhouse with large spaces and panoramic views
Interior

3. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Tavarnelle Val di Pesa
10.0 out of 10, 12, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is NZ$336
includes taxes & fees
15 Sept - 16 Sept
Chianti Craft House Badia a Passignano
Interior

4. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
Montespertoli
10.0 out of 10, 1, (1 review)
"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"
United States
Susan A.
The price is NZ$826
includes taxes & fees
14 Oct - 15 Oct
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
Pool

5. Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
The price is NZ$291
includes taxes & fees
15 Sept - 16 Sept
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Outdoor dining

6. Villa La Stella - Casa per Ferie

Villa La Stella - Casa per Ferie
Le Cure
8.6 out of 10, 253, (253 reviews)
"It’s was great"
United States
Rocio
The price is NZ$257
includes taxes & fees
11 Oct - 12 Oct
Villa La Stella - Casa per Ferie
Exterior detail

7. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, 24, (24 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
The price is NZ$319
includes taxes & fees
15 Sept - 16 Sept
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Smart TV

8. House with separate entrance at the gates of Florence and Chianti

House with separate entrance at the gates of Florence and Chianti
Impruneta
The price is NZ$385
includes taxes & fees
4 Oct - 5 Oct
House with separate entrance at the gates of Florence and Chianti
Dining

9. Leonardo Apartment

Leonardo Apartment
San Gersolé-torre Rosse
The price is NZ$722
includes taxes & fees
29 Sept - 30 Sept
Leonardo Apartment
Outdoor dining

10. GuestHost - Comfortable 30sqm loft that can accommodate up to 3 people. Located on the ground floor of a characteristic building surrounded by Piazzale Galileo greenery, the room is the ideal solution to visit Florence while staying away from the histori

GuestHost - Comfortable 30sqm loft that can accommodate up to 3 people. Located on the ground floor of a characteristic building surrounded by Piazzale Galileo greenery, the room is the ideal solution to visit Florence while staying away from the histori
Oltrarno
10.0 out of 10, 1, (1 review)
"We loved everything about this place. So much so that we almost want to keep it a secret: The location is great (in the hillside above Florence), the space is amazing with high-quality furniture and materials, and the hosts are super friendly and accommodating. The whole place and guest experience are designed with great care and attention to detail. We felt right at home and would return in a heartbeat. If there was one point of critique: I wish the listing had made clear the additional cost...
Germany
Nils F.
The price is NZ$418
includes taxes & fees
25 Sept - 26 Sept
GuestHost - Comfortable 30sqm loft that can accommodate up to 3 people. Located on the ground floor of a characteristic building surrounded by Piazzale Galileo greenery, the room is the ideal solution to visit Florence while staying away from the histori
Interior

11. Your nest in the Tuscany countryside

Your nest in the Tuscany countryside
Certaldo - Firenze
The price is NZ$461
includes taxes & fees
16 Sept - 17 Sept
Your nest in the Tuscany countryside
1 bedroom, in-room safe, desk, iron/ironing board

12. The Wishing Well - The Wishing Well

The Wishing Well - The Wishing Well
Firenze
9.2 out of 10, 5, (5 reviews)
"House was very clean and close enough to the city without the noise or traffic. Host is lovely and responds promptly. Definitely would book again."
Canada
Grace M.
The price is NZ$485
includes taxes & fees
16 Sept - 17 Sept
The Wishing Well - The Wishing Well
Outdoor dining

13. Giotto Apartment with garden

Giotto Apartment with garden
San Gersolé-torre Rosse
10.0 out of 10, 3, (3 reviews)
"The apartment was as pictured – very clean, very comfortable, very bright. The entire grounds were beautiful. Hosts were great and helpful. We wish we stayed longer – and plan on doing so in the future."
United States
Todd G.
The price is NZ$871
includes taxes & fees
14 Oct - 15 Oct
Giotto Apartment with garden
Outdoor dining

14. Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi

Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Certaldo
10.0 out of 10, 1, (1 review)
"Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm."
Germany
Anonymous traveller
The price is NZ$721
includes taxes & fees
28 Sept - 29 Sept
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Dining

15. Brunelleschi Apartment

Brunelleschi Apartment
Impruneta
Brunelleschi Apartment
Property grounds

16. Botticelli Apartment with garden

Botticelli Apartment with garden
San Gersolé-torre Rosse
The price is NZ$979
includes taxes & fees
30 Sept - 1 Oct
Botticelli Apartment with garden
Outdoor dining

17. Citille House

Citille House
San Martino Alla Palma
10.0 out of 10, 1, (1 review)
"An absolutely beautiful, quintessential Tuscan house set in the Chianti hillside. Well appointed house with an extremely attentive host and lovely neighbours. Everything you need and more, including secure onsite, private parking for "
United Kingdom
Anne W.
The price is NZ$621
includes taxes & fees
7 Oct - 8 Oct
Citille House
Terrace/patio

18. Santa Rosa Stables. Modern house in old barn, 5 minutes from historic center

Santa Rosa Stables. Modern house in old barn, 5 minutes from historic center
Oltrarno
10.0 out of 10, 1, (1 review)
"Absolutely beautiful property. AC was efficient in the bedrooms. 2 bathrooms was amazing for 3 of us. Location is quiet and just a short hike outside the busy area. Busses ran frequently enough to make it seem close to everything."
United States
morgan
The price is NZ$563
includes taxes & fees
16 Sept - 17 Sept
Santa Rosa Stables. Modern house in old barn, 5 minutes from historic center
Dining

19. Donatello Apartment

Donatello Apartment
San Gersolé-torre Rosse
Donatello Apartment
Superior Room, City View

20. Bed and Dreams

Bed and Dreams
Florence
7.2 out of 10, 7, (7 reviews)
"AMAZING "
United States
Malfred
The price is NZ$202
includes taxes & fees
1 Oct - 2 Oct
Bed and Dreams
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

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

10/10 Excellent
"This was a good location close to the train station and city center with a short walk. The amenities or the washer and dryer, you can only use one machine at a time which slows the process down. Additionally the pool is only open from 9am - 6 pm and it would be more helpful to have a wider range of hours. The staff was extremely helpful and kind."
Loren 3-night trip
Posted 2 hours ago
The Social Hub Florence Lavagnini

Find out more about San Casciano in Val di Pesa

San Casciano in Val di Pesa Holiday Homes information

Number of reviews
272
Accommodation
1848 Holiday Homes
Lowest Price
NZ$202
Highest Price
NZ$597