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

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Guest favourite
Boutique hotel in Castelfranco Piandiscò
All the Tuscany you're looking for
1 bedroom, 1 bed, 1 private bathroom
22–27 Oct
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4.93 out of 5 average rating, 150 reviews
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Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
4 bedrooms, 6 beds, 4 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
5–10 Sept
New place to stay
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Guest favourite
Flat in Loro Ciuffenna
Farmhouse apartment
2 bedrooms, 2 beds, 1 bathroom
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
1 bedroom, 1 double bed, 1 bathroom
8–13 Nov
4.99 out of 5 average rating, 477 reviews
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Top guest favourite
Flat in Pelago
Tuscan vineyard home. Near Florence
3 bedrooms, 3 beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 72 reviews
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Top guest favourite
Home in Florence
Villa Agnese · Pool · Duomo View · Parking
6 bedrooms, 6 beds, 4.5 bathrooms
24–29 Oct
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Villa in Noce
Historic villa with private pool in Tuscany
2 bedrooms, 4 beds, 2 bathrooms
11–16 Nov
5.0 out of 5 average rating, 35 reviews
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Top guest favourite
Villa in Modine
Tuscan Villa with Private Jacuzzi & River
6 bedrooms, 7 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 51 reviews
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Superhost
Home in Galenda
Casa Pernice · Chianti villa with private pool
3 bedrooms, 3 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
2 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 34 reviews
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Top guest favourite
Home in Pontassieve
La Quercia House in the countryside
3 bedrooms, 6 beds, 2 bathrooms
9–14 Oct
5.0 out of 5 average rating, 66 reviews
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Top guest favourite
Flat in Poppi
Country chill in the heart of a medieval village
3 bedrooms, 4 beds, 1 bathroom
6–11 Sept
4.97 out of 5 average rating, 32 reviews
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Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 140 reviews
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Villa in Montevarchi
Designer Villa with Private Garden & Jacuzzi
3 bedrooms, 3 king beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Superhost
Apartment in Loro Ciuffenna
Ginestra superior flat in VILLA with POOL
2 bedrooms, 3 beds, 2 bathrooms
3–8 Sept
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Top guest favourite
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Flat in Rignano sull'Arno
Gemini Apartment
1 bedroom, 1 double bed, 1 bathroom
29 Sept – 4 Oct
4.94 out of 5 average rating, 18 reviews
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Superhost
Holiday home in Rosennano
HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL
2 bedrooms, 6 beds, 3 bathrooms
22–27 Sept
4.99 out of 5 average rating, 76 reviews