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

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
Superhost
Home in Figline e Incisa Valdarno
Villa among our vineyards on the outskirts of Chianti
Business host
14–19 Sept
New place to stay
Top guest favourite
Farm stay in Stia
Tuscany Magic @ Montermoli
Business host
19–26 Sept
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Loro Ciuffenna
Farmhouse apartment
Business host
4–9 Oct
5.0 out of 5 average rating, 16 reviews
Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
Business host
14–19 Sept
5.0 out of 5 average rating, 4 reviews
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
Guest favourite
Home in Bagno A Ripoli
Historic Stone Villa | Pool | 15min Florence
Individual host
1–6 Oct
5.0 out of 5 average rating, 12 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
Top guest favourite
Home in Florence
Villa Agnese · Pool · Duomo View · Parking
Individual host
24–29 Oct
5.0 out of 5 average rating, 19 reviews
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
Villa in Montevarchi
Designer Villa with Private Garden & Jacuzzi
Business host
30 Sept – 5 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Terranuova Bracciolini
Villa Piandarca - Tuscany - WIFI - private pool
Individual host
25–30 Sept
4.98 out of 5 average rating, 59 reviews
Guest favourite
Home in Bagno A Ripoli
Casa Spiano
Business host
24–29 Sept
5.0 out of 5 average rating, 9 reviews
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
Top guest favourite
Holiday home in Rosennano
HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL
Business host
22–27 Sept
4.99 out of 5 average rating, 78 reviews
Top guest favourite
Home in Farneta
Podere Bocci residence in Casentino - Entire Villa
Business host
3–8 Oct
5.0 out of 5 average rating, 49 reviews
Superhost
Apartment in Loro Ciuffenna
Ginestra superior flat in VILLA with POOL
Business host
14–19 Sept
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