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

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Top guest favourite
Villa in Gaiole in Chianti
Sestuccina
2 bedrooms, 2 beds, 2 shared bathrooms
31 Oct – 7 Nov, Individual host
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4.93 out of 5 average rating, 46 reviews
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Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
Individual host
26 Sept – 3 Oct
5.0 out of 5 average rating, 34 reviews
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Top guest favourite
Villa in Gaiole in Chianti
Galendino
Business host
19–26 Sept
5.0 out of 5 average rating, 9 reviews
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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, 29 reviews
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Home in Gaiole in Chianti
Borgo di Gaiole – Stylish Home in Chianti
Individual host
1–6 Sept
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Guest favourite
Home in Moncioni
Private Tuscan hilltop farmhouse with pool
Individual host
1–6 Sept
4.9 out of 5 average rating, 30 reviews
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Luxe
Home in Gaiole in Chianti
La Tuscia – Tuscan Estate, Boutique Villa
Business host
16–21 Oct
5.0 out of 5 average rating, 22 reviews
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Guest favourite
Villa in Gaiole in Chianti
Casa Faraona, villa with private pool
Business host
1–6 Oct
5.0 out of 5 average rating, 31 reviews
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Guest favourite
Home in Gaiole in Chianti
Exclusive private villa with private pool
Business host
29 Sept – 4 Oct
5.0 out of 5 average rating, 8 reviews
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Flat in Gaiole in Chianti
Podere L'Aquila- Agapanto
Business host
21–26 Sept
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
1–6 Sept
New place to stay
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Superhost
Room in Gaiole in Chianti
Argentina. Welcome to our little village, L...
Business host
14–19 Oct
4.95 out of 5 average rating, 20 reviews
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Flat in Gaiole in Chianti
Mill in Chianti - Rosa
Individual host
18–23 Sept
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Superhost
Home in Gaiole in Chianti
Villa Melina - new life for the barn
Business host
16–21 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
6–11 Sept
4.99 out of 5 average rating, 112 reviews
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Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
Individual host
12–17 Oct
4.98 out of 5 average rating, 82 reviews
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Superhost
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
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Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
Business host
26–31 Oct
4.99 out of 5 average rating, 68 reviews
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Guest favourite
Home in Greve in Chianti
Original Tuscan Experience in the Heart of Chianti
Business host
14–19 Dec
5.0 out of 5 average rating, 23 reviews