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

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, 343 reviews
Top guest favourite
Flat in Loro Ciuffenna
Farmhouse apartment
Business host
4–9 Oct
5.0 out of 5 average rating, 16 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
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
Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
Business host
14–19 Sept
5.0 out of 5 average rating, 4 reviews
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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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 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
Villa in Gaiole in Chianti
Montemarcoli
Individual host
7–12 Nov
5.0 out of 5 average rating, 34 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 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
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
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
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
Villa in Impruneta
Exclusive Estate: Concierge service & heated pool
Individual host
4–9 Oct
4.99 out of 5 average rating, 145 reviews
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
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