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

Top guest favourite
Flat in San Casciano In Val di Pesa
Timeless Beauty in Chianti | 20 min da Firenze AC
2 bedrooms, 5 beds, 1 private bathroom
27 Sept – 2 Oct, Individual host
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4.89 out of 5 average rating, 199 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, 11 reviews
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
Flat in San Casciano In Val di Pesa
Chianti Prestige Apartment • Terrazza & Relax
Individual host
10–15 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, 89 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, 55 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
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
Flat in Montespertoli
La Casa di Madina – Flo Apartments
Business host
26 Sept – 1 Oct
5.0 out of 5 average rating, 10 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 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 Le Quattro Strade
Villa Quattro Strade in Chianti
Individual host
7–12 Oct
5.0 out of 5 average rating, 5 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
Guest favourite
Villa in Montespertoli
Villa Moneta, a Slice of Tuscan Paradise
Individual host
10–15 Sept
5.0 out of 5 average rating, 12 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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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