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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, 339 reviews
Guest favourite
Home in Moncioni
Private Tuscan hilltop farmhouse with pool
Individual host
5–10 Sept
4.9 out of 5 average rating, 30 reviews
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, 84 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
Business host
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Loro Ciuffenna
Farmhouse apartment
Business host
4–9 Oct
5.0 out of 5 average rating, 15 reviews
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, 17 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 Pergine Valdarno
La Vignaccia (Farmhouse) - villa w/private pool
Business host
26 Sept – 3 Oct
4.96 out of 5 average rating, 101 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, 76 reviews
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
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
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
Top guest favourite
Villa in Noce
Villa in Tuscany with a private panoramic swimming pool
Business host
11–16 Nov
5.0 out of 5 average rating, 35 reviews
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, 479 reviews
Superhost
Apartment in Loro Ciuffenna
Ginestra superior flat in VILLA with POOL
Business host
3–8 Sept
Top guest favourite
Home in Farneta
Podere Bocci residence in Casentino - Entire Villa
Business host
5–10 Sept
5.0 out of 5 average rating, 48 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