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

Guest favourite
Farm stay in Gaiole in Chianti
Il Nido - a romantic hearth
1 bedroom, 1 bed, 1 private bathroom
11–16 Nov, Business host
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4.94 out of 5 average rating, 260 reviews
Top guest favourite
Villa in Gaiole in Chianti
Sestuccia
Individual host
25 Sept – 2 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
Business host
29 Sept – 4 Oct
5.0 out of 5 average rating, 30 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 Gaiole in Chianti
Galendino
Business host
10–17 Oct
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Villa in Gaiole in Chianti
Sestuccina
Individual host
31 Oct – 7 Nov
4.93 out of 5 average rating, 46 reviews
Guest favourite
Villa in Gaiole in Chianti
Riecine Capanna 4
Business host
1–6 Nov
5.0 out of 5 average rating, 9 reviews
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
Guest favourite
Villa in Gaiole in Chianti
Villa Il Masseto
Business host
10–15 Oct
5.0 out of 5 average rating, 6 reviews
Home in Gaiole in Chianti
Borgo di Gaiole – Stylish Home in Chianti
Individual host
19–24 Oct
Guest favourite
Home in Radda in Chianti
Villa le Scope 5*
Individual host
27 Sept – 2 Oct
4.98 out of 5 average rating, 50 reviews
Guest favourite
Home in Gaiole in Chianti
Exclusive private villa with private pool
Business host
18–23 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Farm stay in Gaiole in Chianti
Le Rondini - where it all began
Business host
1–6 Nov
4.84 out of 5 average rating, 109 reviews
Luxe
Home in Gaiole in Chianti
La Tuscia – Tuscan Estate, Boutique Villa
Business host
25–30 Oct
5.0 out of 5 average rating, 22 reviews
Flat in Gaiole in Chianti
Podere L'Aquila- Agapanto
Business host
21–26 Sept
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
Home in Gaiole in Chianti
San Piero Terre, villa in the Chianti region.
Individual host
20–25 Sept
4.67 out of 5 average rating, 18 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 Cavriglia
Villa Poggio in Mandria in Chianti
Business host
7–12 Oct
4.99 out of 5 average rating, 162 reviews