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

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Guest favourite
Apartment in Castelfranco Piandiscò
From Beppa B&B
1 bedroom, 1 bed, 1 private bathroom
1–6 Jan, Individual host
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4.85 out of 5 average rating, 54 reviews
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Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
Business host
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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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
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
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Guest favourite
Home in Moncioni
Private Tuscan hilltop farmhouse with pool
Individual host
1–6 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
5–10 Sept
New place to stay
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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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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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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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Superhost
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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Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
Individual host
12–17 Oct
4.98 out of 5 average rating, 82 reviews
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Superhost
Holiday home in Rosennano
HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL
Business host
22–27 Sept
4.99 out of 5 average rating, 76 reviews
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Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
Individual host
1–6 Sept
4.98 out of 5 average rating, 60 reviews
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Top guest favourite
Villa in Gaiole in Chianti
Galendino
Business host
19–26 Sept
5.0 out of 5 average rating, 10 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, 56 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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Guest favourite
Farm stay in Loro Ciuffenna
Exclusive villa with pool and breathtaking view
Business host
7–12 Sept
5.0 out of 5 average rating, 6 reviews
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Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
Business host
24–29 Oct
5.0 out of 5 average rating, 15 reviews