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

Top guest favourite
Home in San Casciano In Val di Pesa
The Chianti Classico Sunset
1 bedroom, 1 bed, 1 private bathroom
2–7 Oct, Individual host
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4.98 out of 5 average rating, 242 reviews
Superhost
Villa in San Casciano In Val di Pesa
Villa Casavecchia 26+ people
Individual host
14–19 Nov
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, 10 reviews
Top guest favourite
Villa in Impruneta
Private Estate - Personal Concierge & heated pool
Individual host
4–9 Oct
4.99 out of 5 average rating, 145 reviews
Top guest favourite
Holiday home in San Casciano In Val di Pesa
Mucciana 3
Individual host
6–11 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Barberino Tavarnelle
Relaxing Tuscan Country Home with Beautiful Views
Individual host
3–8 Nov
5.0 out of 5 average rating, 87 reviews
Top guest favourite
Home in San Casciano In Val di Pesa
Authentic Tuscan home: history, wine and relax
Individual host
20–25 Sept
5.0 out of 5 average rating, 44 reviews
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
29 Nov – 4 Dec
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
Business host
20–25 Oct
5.0 out of 5 average rating, 141 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
Featured hotel
Room in Florence
Classic room
Business host
1–6 Nov
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
Guest favourite
Villa in Le Quattro Strade
Villa Quattro Strade in Chianti
Individual host
7–12 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Barberino Tavarnelle
Le Casette Altana Farm
Business host
7–12 Oct
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
6–11 Sept
4.99 out of 5 average rating, 113 reviews
Guest favourite
Home in San Casciano In Val di Pesa
“ Giorgio” Tuscan barn
Individual host
24–29 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Villa in Montespertoli
Villa Moneta, a Slice of Tuscan Paradise
Individual host
7–12 Sept
5.0 out of 5 average rating, 12 reviews