filters

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
,
4.85 out of 5 average rating, 34 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, 11 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
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
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 6 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, 221 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
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
Superhost
Villa in San Casciano In Val di Pesa
Villa Casavecchia 26+ people
Individual host
14–19 Nov
Top guest favourite
Farm stay in Barberino Val d'Elsa
Apartment in a farmhouse in Chianti
Business host
7–12 Oct
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Bagno A Ripoli
Casa Spiano
Business host
24–29 Sept
5.0 out of 5 average rating, 8 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
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
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
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
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
27 Oct – 1 Nov
4.99 out of 5 average rating, 114 reviews
Superhost
Farm stay in San Casciano In Val di Pesa
Tuscan Vacation Home
Individual host
1–6 Oct