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

Top guest favourite
Farm stay in Gaiole in Chianti
La Pieve - the house next to the church
2 bedrooms, 3 beds, 1 private bathroom
4–9 Nov
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4.96 out of 5 average rating, 110 reviews
Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
5.0 out of 5 average rating, 25 reviews, 5 bedrooms, 5 beds, 5 bathrooms
28 Jul – 2 Aug
Top guest favourite
Villa in Gaiole in Chianti
Casa Faraona, villa with private pool
5.0 out of 5 average rating, 29 reviews, 3 bedrooms, 4 beds, 3 bathrooms
29 Aug – 3 Sept
Top guest favourite
Villa in Gaiole in Chianti
Sestuccia
4.99 out of 5 average rating, 69 reviews, 4 bedrooms, 4 beds, 4 bathrooms
24–31 Oct
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
Luxe
Villa in Gaiole in Chianti
Le Pratola
5.0 out of 5 average rating, 6 reviews, 7 bedrooms, 11 beds, 7.5 bathrooms
18–25 Jul
Top guest favourite
Home in Montebenichi
[Little Escape] 4 Beds + Private Panoramic Pool
5.0 out of 5 average rating, 72 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Aug
Villa in Montevarchi
Designer Villa with Private Garden & Jacuzzi
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Flat in Cavriglia
Apartment Comfort | Quiet Escape in Tuscany
5.0 out of 5 average rating, 12 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Superhost
Flat in Bossi
Villino Ersilia Music, the charm of Chianti
2 bedrooms, 3 beds, 2 bathrooms
7–12 Jul
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
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
4.97 out of 5 average rating, 72 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Oct
Superhost
Home in Moncioni
Tuscany hilltop farmhouse with pool and treehouse
4.88 out of 5 average rating, 26 reviews, 5 bedrooms, 7 beds, 4 bathrooms
13–18 Aug
Guest favourite
Farm stay in Gaiole in Chianti
Le Miccine Villa in Tuscany for 6 w/ Pool
4.92 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
4.98 out of 5 average rating, 64 reviews, 5 bedrooms, 5 beds, 5 bathrooms
26–31 Oct
Superhost
Apartment in Gaiole in Chianti
Casa Livio, a garden with a view
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 2 bathrooms
9–14 Jul
Top guest favourite
Flat in San Gusmè
Beautiful medieval village!!!
4.99 out of 5 average rating, 460 reviews, 2 bedrooms, 2 beds, 2 bathrooms
26–31 Oct
Flat in Cavriglia
Malva - Superior Stay in the Tuscan Hills
2 bedrooms, 3 beds, 1 bathroom
27 Aug – 1 Sept
Top guest favourite
Villa in Cavriglia
Villa Poggio in Mandria in Chianti
4.99 out of 5 average rating, 156 reviews, 5 bedrooms, 8 beds, 5.5 bathrooms
29 Aug – 3 Sept