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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
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
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
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
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
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
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
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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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