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

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Guest favourite
Home in San Casciano V.Pesa (FI)
Ambrogetta by Interhome.
4 bedrooms, 3 private bathrooms
3–10 Oct, Business host
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4.85 out of 5 average rating, 34 reviews
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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, 13 reviews
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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
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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
Peaceful Tuscan Home with Breathtaking Views
Individual host
20–25 Nov
5.0 out of 5 average rating, 90 reviews
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Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 6 reviews
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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
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
16–21 Sept
New place to stay
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Superhost
Villa in San Casciano In Val di Pesa
Villa Casavecchia 26+ people
Individual host
18–23 Oct
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Top guest favourite
Flat in Rignano sull'Arno
VIRGO apartment
Business host
24–29 Sept
5.0 out of 5 average rating, 27 reviews
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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
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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, 222 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, 8 reviews
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Guest favourite
Home in Bagno A Ripoli
Casa Spiano
Business host
24–29 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Villa in Barberino Tavarnelle
Valluccia 51
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 50 reviews
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Superhost
Rooms in Montespertoli
i Casciani - Depéndance
Business host
15–20 Oct
5.0 out of 5 average rating, 3 reviews
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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
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Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
Individual host
17–24 Oct
5.0 out of 5 average rating, 19 reviews
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Superhost
Home in Figline e Incisa Valdarno
Villa among our vineyards on the outskirts of Chianti
Business host
16–21 Sept
New place to stay