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

Top guest favourite
Home in Castelfranco Piandiscò
Casa Macchia /Florence charming villa private Pool
6 bedrooms, 9 beds, 3 private bathrooms
3–10 Jul, Individual host
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4.96 out of 5 average rating, 101 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
11–16 Sept
5.0 out of 5 average rating, 4 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
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, 11 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, 59 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, 77 reviews
Guest favourite
Home in Bagno A Ripoli
Casa Spiano
Business host
24–29 Sept
5.0 out of 5 average rating, 8 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 Galenda
Casa Pernice · Chianti villa with private pool
Business host
7–12 Oct
5.0 out of 5 average rating, 15 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
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
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
Villa in Barberino Tavarnelle
Valluccia 51
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 49 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
Home in Farneta
Podere Bocci residence in Casentino - Entire Villa
Business host
3–8 Oct
5.0 out of 5 average rating, 49 reviews
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