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

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Top guest favourite
Villa in San Casciano In Val di Pesa
Il Vichiaccio: Florence Villa with Jacuzzi
4 bedrooms, 7 beds, 3 private bathrooms
7–12 Sept, Business host
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4.95 out of 5 average rating, 202 reviews
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Superhost
Villa in San Casciano In Val di Pesa
Villa Casavecchia 26+ people
Individual host
14–19 Nov
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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
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Top guest favourite
Holiday home in San Casciano In Val di Pesa
Mucciana 3
Individual host
4–9 Sept
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Home in San Casciano In Val di Pesa
Authentic Tuscan home: history, wine and relax
Individual host
2–7 Sept
5.0 out of 5 average rating, 44 reviews
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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
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
19–24 Oct
5.0 out of 5 average rating, 53 reviews
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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
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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, 86 reviews
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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
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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
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Flat in San Casciano In Val di Pesa
Podere Papèra - Capriolo flatbread
Business host
25–30 Sept
5.0 out of 5 average rating, 3 reviews
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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
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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
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Guest favourite
Flat in Barberino Tavarnelle
Le Casette Altana Farm
Business host
7–12 Oct
5.0 out of 5 average rating, 10 reviews
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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
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Flat in San Casciano In Val di Pesa
Cottage in Chianti
Business host
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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Home in Poggibonsi
Le Casacce Farmhouse
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 4 reviews