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Search results; Over 1,000 homes in Castelfranco di Sopra

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Superhost
Apartment in Castelfranco di Sopra
House between Firenze, Arezzo, chianti e Siena
1 bedroom, 1 bed, 1 shared bathroom
22–27 Oct, Business host
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4.84 out of 5 average rating, 300 reviews
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Top guest favourite
Flat in Loro Ciuffenna
Farmhouse apartment
Business host
4–9 Oct
5.0 out of 5 average rating, 16 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
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
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Guest favourite
Home in Moncioni
Private Tuscan hilltop farmhouse with pool
Individual host
19–24 Sept
4.9 out of 5 average rating, 30 reviews
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Top guest favourite
Farm stay in Greve in Chianti
Old hayloft on the Chianti hills
Business host
12–17 Feb
4.99 out of 5 average rating, 481 reviews
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Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
Business host
16–21 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
Individual host
7–12 Nov
5.0 out of 5 average rating, 34 reviews
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Villa in Montevarchi
Designer Villa with Private Garden & Jacuzzi
Business host
30 Sept – 5 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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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 Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
Business host
3–8 Oct
5.0 out of 5 average rating, 33 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
Villa in Gaiole in Chianti
Galendino
Business host
10–17 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
27 Oct – 1 Nov
4.99 out of 5 average rating, 114 reviews
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Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
Business host
29 Sept – 4 Oct
5.0 out of 5 average rating, 30 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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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
Villa in Modine
Tuscan Villa with Private Jacuzzi & River
Business host
30 Oct – 4 Nov
5.0 out of 5 average rating, 51 reviews