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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, 243 reviews
Superhost
Villa in San Casciano In Val di Pesa
Villa Casavecchia 26+ people
Individual host
14–19 Nov
Top guest favourite
Villa in Impruneta
Exclusive Estate: Concierge service & heated pool
Individual host
4–9 Oct
4.99 out of 5 average rating, 145 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
Guest favourite
Flat in San Casciano In Val di Pesa
Chianti Prestige Apartment • Terrazza & Relax
Individual host
7–12 Sept
5.0 out of 5 average rating, 10 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, 87 reviews
Top guest favourite
Home in San Casciano In Val di Pesa
Authentic Tuscan home: history, wine and relax
Individual host
20–25 Oct
5.0 out of 5 average rating, 44 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
Guest favourite
Flat in Montespertoli
La Casa di Madina – Flo Apartments
Business host
8–13 Sept
5.0 out of 5 average rating, 10 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
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
Top guest favourite
Holiday home in San Casciano In Val di Pesa
Mucciana 3
Individual host
10–15 Sept
5.0 out of 5 average rating, 12 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
Top guest favourite
Room in San Casciano In Val di Pesa
Independent loft in the heart of Chianti
Individual host
4–9 Oct
5.0 out of 5 average rating, 64 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, 3 reviews
Top guest favourite
Flat in Barberino Tavarnelle
Le Casette Altana Farm
Business host
7–12 Oct
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
21–26 Nov
5.0 out of 5 average rating, 54 reviews
Flat in San Casciano In Val di Pesa
Cottage in Chianti
Business host
13–18 Sept
5.0 out of 5 average rating, 4 reviews