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

Descriptions are based on details hosts provide
Superhost
Cottage in Gaiole in Chianti
Old Chianti chapel-style cottage
2 bedrooms, 2 beds, 1 private bathroom
21–28 Aug
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4.84 out of 5 average rating, 131 reviews
Guest favourite
Flat in Cavriglia
Ancient borgo with a panoramic pool
5.0 out of 5 average rating, 15 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Aug
Top guest favourite
Villa in Gaiole in Chianti
Wine estate villa in Chianti Classico
5.0 out of 5 average rating, 25 reviews, 5 bedrooms, 5 beds, 5 bathrooms
28 Jul – 2 Aug
Luxe
Villa in Gaiole in Chianti
Hilltop villa with 360-degree Chianti views
5.0 out of 5 average rating, 6 reviews, 7 bedrooms, 11 beds, 7.5 bathrooms
4–9 Sept
Guest favourite
Villa in Gaiole in Chianti
Casa Faraona, villa with private pool
5.0 out of 5 average rating, 30 reviews, 3 bedrooms, 4 beds, 3 bathrooms
29 Aug – 3 Sept
Guest favourite
Villa in Gaiole in Chianti
La Fornace di Tremoleto-Villa with Private Pool
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Aug
Superhost
Holiday home in Montegonzi
Vino apartment 70 m2 view swimming pool
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 4 beds, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Farm stay in Gaiole in Chianti
Medieval hamlet amid Chianti Classico vineyards
4.84 out of 5 average rating, 109 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Top guest favourite
Villa in Gaiole in Chianti
Pool, spa, and vineyard in Chianti
4.99 out of 5 average rating, 69 reviews, 4 bedrooms, 4 beds, 4 bathrooms
24–31 Oct
Top guest favourite
Home in Montebenichi
Tuscan hillside views and a private pool
5.0 out of 5 average rating, 73 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
4–9 Sept
Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
5.0 out of 5 average rating, 33 reviews, 2 bedrooms, 3 beds, 2 bathrooms
7–14 Nov
Villa in Montevarchi
Designer Villa with Private Garden & Jacuzzi
3 bedrooms, 3 beds, 2 bathrooms
18–23 Jul
Guest favourite
Home in Gaiole in Chianti
Montelucci Chianti Agrivilla
5.0 out of 5 average rating, 7 reviews, 7 bedrooms, 11 beds, 6 bathrooms
18–23 Oct
Guest favourite
Villa in Gaiole in Chianti
Stone villa with town views and hot tub
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 3 bathrooms
26–31 Jul
Guest favourite
Home in Radda in Chianti
Villa le Scope 5*
4.98 out of 5 average rating, 45 reviews, 3 bedrooms, 4 beds, 3 bathrooms
28 Jul – 2 Aug
Top guest favourite
Flat in Quercegrossa
Renovated farmhouse on a Chianti winery
4.97 out of 5 average rating, 72 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
18–23 Oct
Top guest favourite
Cottage in Greve in Chianti
Very cosy cottage with beautiful views
5.0 out of 5 average rating, 50 reviews, 3 bedrooms, 4 beds, 3 bathrooms
4–10 Oct
Superhost
Flat in Cavriglia
Malva - Superior Stay in the Tuscan Hills
2 bedrooms, 3 beds, 1 bathroom
16–21 Sept
Top guest favourite
Home in Greve in Chianti
16th-century estate among Chianti vineyards
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 2 beds, 2 bathrooms
4–9 Aug