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Search results; Over 1,000 homes in Gaiole in Chianti

Guest favourite
Villa in Gaiole in Chianti
Casa Faraona, villa with private pool
3 bedrooms, 4 beds, 3 private bathrooms
1–6 Oct
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5.0 out of 5 average rating, 31 reviews
Top guest favourite
Villa in Gaiole in Chianti
Sestuccia
4 bedrooms, 4 king beds, 4 bathrooms
17–24 Oct
4.99 out of 5 average rating, 74 reviews
Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
5 bedrooms, 1 bed, 5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Farm stay in Gaiole in Chianti
La Pieve - the house next to the church
2 bedrooms, 3 beds, 1 bathroom
13–18 Nov
4.97 out of 5 average rating, 116 reviews
Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
2 bedrooms, 3 beds, 2 bathrooms
7–12 Nov
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Villa in Gaiole in Chianti
Sestuccina
2 bedrooms, 2 king beds, 2 bathrooms
31 Oct – 7 Nov
4.93 out of 5 average rating, 46 reviews
Guest favourite
Villa in Gaiole in Chianti
Riecine Capanna 4
2 bedrooms, 2 double beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 9 reviews
Guest favourite
Villa in Gaiole in Chianti
Villa Il Masseto
4 bedrooms, 3 double beds, 3 bathrooms
10–15 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Villa in Gaiole in Chianti
Galendino
2 bedrooms, 2 beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 10 reviews
Guest favourite
Villa in Gaiole in Chianti
La Fornace di Tremoleto-Villa with Private Pool
3 bedrooms, 3 double beds, 2 bathrooms
8–13 Oct
4.92 out of 5 average rating, 13 reviews
Home in Gaiole in Chianti
Borgo di Gaiole - Stylish Home in Chianti
3 bedrooms, 6 single beds, 2 bathrooms
19–24 Oct
Guest favourite
Home in Moncioni
Private Tuscan hilltop farmhouse with pool
5 bedrooms, 7 beds, 4 bathrooms
19–24 Sept
4.9 out of 5 average rating, 30 reviews
Top guest favourite
Villa in Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
5 bedrooms, 5 double beds, 5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Villa in Cavriglia
Villa Poggio in Mandria in Chianti
5 bedrooms, 8 beds, 5.5 bathrooms
7–12 Oct
4.99 out of 5 average rating, 162 reviews
Superhost
Home in Gaiole in Chianti
Villa Melina - new life for the barn
1 bedroom, 1 bed, 1 bathroom
10–15 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Ambra
Chianti Villa in Tuscany near Siena and Arezzo
5 bedrooms, 6 beds, 4 bathrooms
22–27 Sept
4.99 out of 5 average rating, 149 reviews
Guest favourite
Home in Gaiole in Chianti
Exclusive private villa with private pool
6 bedrooms, 9 beds, 6 bathrooms
18–23 Oct
5.0 out of 5 average rating, 8 reviews
Flat in Gaiole in Chianti
Podere L'Aquila- Agapanto
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay