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Search results; Over 1,000 homes in San Casciano in Val di Pesa

Guest favourite
Home in San Casciano V.Pesa (FI)
Ambrogetta by Interhome.
4 bedrooms, 3 private bathrooms
3–10 Oct, Business host
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4.85 out of 5 average rating, 34 reviews
Top guest favourite
Home in Barberino Tavarnelle
Peaceful Tuscan Home with Breathtaking Views
Individual host
3–8 Nov
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Holiday home in San Casciano In Val di Pesa
Mucciana 3
Individual host
19–24 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Villa in San Casciano In Val di Pesa
Archipettoli - Exclusive villa 360 view AC WIFI
Individual host
19–26 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
Individual host
2–7 Oct
5.0 out of 5 average rating, 30 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Apartment in Noce
Historic 17th-century villa in Chianti, Tuscany
Business host
11–16 Nov
5.0 out of 5 average rating, 222 reviews
Superhost
Villa in San Casciano In Val di Pesa
Villa Casavecchia 26+ people
Individual host
14–19 Nov
Superhost
Farm stay in San Casciano In Val di Pesa
Tuscan Vacation Home
Individual host
1–6 Oct
Top guest favourite
Flat in Rignano sull'Arno
VIRGO apartment
Business host
20–25 Sept
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Villa in Barberino Tavarnelle
Chianti Holidays, Il Poggetto by Alfina
Individual host
20–25 Sept
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Greve in Chianti
Villa with swimming pool in the heart of Chianti | Florence
Individual host
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Barn in Pontassieve
Your little slice of paradise near Florence
Individual host
15–20 Nov
5.0 out of 5 average rating, 22 reviews
Superhost
Rooms in Montespertoli
i Casciani - Depéndance
Business host
15–20 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
Individual host
31 Oct – 7 Nov
5.0 out of 5 average rating, 19 reviews
Flat in Certaldo
La Casa di Mario: Apt near Siena and Florence
Business host
12–17 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
Business host
7–12 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Farm stay in Certaldo
Farmhouse exclusive use Chianti area infinity pool
Business host
18–23 Oct
5.0 out of 5 average rating, 30 reviews