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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, 111 reviews
Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
5 bedrooms, 5 beds
28 Jul – 2 Aug
5.0 out of 5 average rating, 25 reviews
Guest favourite
Villa in Gaiole in Chianti
Casa Faraona, villa with private pool
3 bedrooms, 4 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Villa in Gaiole in Chianti
Sestuccia
4 bedrooms, 4 king beds
24–31 Oct
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
2 bedrooms, 3 beds
7–14 Nov
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
5 bedrooms, 5 king beds
26–31 Oct
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Flat in Cavriglia
Apartment Comfort | Quiet Escape in Tuscany
1 bedroom, 1 bed
24–29 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Montebenichi
[Little Escape] 4 Beds + Private Panoramic Pool
2 bedrooms, 2 double beds
20–25 Aug
5.0 out of 5 average rating, 72 reviews
Villa in Montevarchi
Designer Villa with Private Garden & Jacuzzi
3 bedrooms, 3 king beds
5–10 Jul
New place to stay
Top guest favourite
Flat in San Gusmè
Beautiful medieval village!!!
2 bedrooms, 2 double beds
26–31 Oct
4.99 out of 5 average rating, 460 reviews
Top guest favourite
Farm stay in Gaiole in Chianti
Le Rondini - where it all began
2 bedrooms, 3 beds
23–28 Aug
4.84 out of 5 average rating, 109 reviews
Holiday home in Montegonzi
Vino apartment 70 m2 view swimming pool
1 bedroom, 4 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Farm stay in Gaiole in Chianti
Le Miccine Villa in Tuscany for 6 w/ Pool
3 bedrooms, 4 beds
23–28 Aug
4.92 out of 5 average rating, 12 reviews
Guest favourite
Villa in Gaiole in Chianti
Villa Il Masseto
3 bedrooms, 3 double beds
6–11 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms, 3 beds
16–21 Oct
4.97 out of 5 average rating, 72 reviews
Luxe
Villa in Gaiole in Chianti
Le Pratola
7 bedrooms, 11 beds
18–25 Jul
5.0 out of 5 average rating, 6 reviews
Superhost
Apartment in Gaiole in Chianti
Casa Livio, a garden with a view
2 bedrooms, 2 beds
9–14 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Cavriglia
Villa Poggio in Mandria in Chianti
5 bedrooms, 8 beds
29 Aug – 3 Sept
4.99 out of 5 average rating, 156 reviews
Flat in Cavriglia
Malva - Superior Stay in the Tuscan Hills
2 bedrooms, 3 beds
13–18 Sept