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

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Guest favourite
Farm stay in Castelfranco di sopra
Romantic apartment in the Tuscan village
1 bedroom, 1 bed, 1.5 private bathrooms
25–30 Oct, Business host
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4.89 out of 5 average rating, 339 reviews
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Top guest favourite
Home in Florence
Villa Agnese · Pool · Duomo View · Parking
Individual host
24–29 Oct
5.0 out of 5 average rating, 16 reviews
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Guest favourite
Home in Moncioni
Private Tuscan hilltop farmhouse with pool
Individual host
3–8 Sept
4.9 out of 5 average rating, 30 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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Guest favourite
Home in Bagno A Ripoli
Historic Stone Villa | Pool | 15min Florence
Individual host
4–9 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Villa in Vicchio
Apartment in Villa with park and private spa
Individual host
1–6 Sept
5.0 out of 5 average rating, 55 reviews
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Top guest favourite
Flat in Pelago
Tuscan vineyard home. Near Florence
Individual host
10–17 Oct
5.0 out of 5 average rating, 72 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, 15 reviews
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Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
Individual host
29 Oct – 3 Nov
4.98 out of 5 average rating, 82 reviews
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Superhost
Apartment in Loro Ciuffenna
Ginestra superior flat in VILLA with POOL
Business host
3–8 Sept
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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, 14 reviews
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Villa in Montevarchi
Designer Villa with Private Garden & Jacuzzi
Business host
2–7 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Terranuova Bracciolini
Villa Piandarca - Tuscany - WIFI - private pool
Individual host
12–17 Sept
4.98 out of 5 average rating, 57 reviews
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Top guest favourite
Farm stay in Stia
Tuscany Magic @ Montermoli
Business host
12–19 Sept
5.0 out of 5 average rating, 27 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 Modine
Tuscan Villa with Private Jacuzzi & River
Business host
30 Oct – 4 Nov
5.0 out of 5 average rating, 51 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, 3 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, 49 reviews
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Top guest favourite
Farm stay in Greve in Chianti
Old hayloft on the Chianti hills
Business host
8–13 Nov
4.99 out of 5 average rating, 478 reviews