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

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Top guest favourite
Home in San Casciano In Val di Pesa
The Chianti Classico Sunset
1 bedroom, 1 bed, 1 private bathroom
1–6 Mar, Individual host
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4.98 out of 5 average rating, 243 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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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
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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Guest favourite
Flat in San Casciano In Val di Pesa
Chianti Prestige Apartment • Terrazza & Relax
Individual host
27 Sept – 2 Oct
5.0 out of 5 average rating, 10 reviews
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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
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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
Flat in Montespertoli
La Casa di Madina – Flo Apartments
Business host
26 Sept – 1 Oct
5.0 out of 5 average rating, 10 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
20–25 Oct
5.0 out of 5 average rating, 45 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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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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Top 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, 7 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
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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Superhost
Farm stay in San Casciano In Val di Pesa
Tuscan Vacation Home
Individual host
1–6 Oct
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Flat in San Casciano In Val di Pesa
Cottage in Chianti
Business host
16–21 Sept
5.0 out of 5 average rating, 4 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, 65 reviews
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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