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

Guest favourite
Home in Gaiole in Chianti
Charming estate with views. A/C in the bedrooms
2 bedrooms, 2 beds, 1 private bathroom
18–23 Sept
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4.86 out of 5 average rating, 290 reviews
Guest favourite
Villa in Gaiole in Chianti
Villa Il Masseto
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 3 bathrooms
6–11 Jul
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
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
3–8 Jul
Flat in Gaiole in Chianti
Podere L'Aquila- Agapanto
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
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
6–11 Jul
Top guest favourite
Flat in Radda in Chianti
Heart of Chianti - a warm flat in Radda
4.92 out of 5 average rating, 123 reviews, 1 bedroom, 1 bed, 1 bathroom
6–11 Jul
Superhost
Home in Gaiole in Chianti
Villa Melina - new life for the barn
1 bedroom, 1 bed, 1 bathroom
11–16 Aug
Top guest favourite
Farm stay in Radda in Chianti
1500 Stone House in Chianti Heart private lake B
4.97 out of 5 average rating, 101 reviews, 2 bedrooms, 3 beds, 1 bathroom
4–9 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
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
Luxe
Home in Gaiole in Chianti
La Tuscia – Tuscan Estate, Boutique Villa
5.0 out of 5 average rating, 22 reviews, 4 bedrooms, 4 beds, 5 bathrooms
15–20 Aug
Top guest favourite
Farm stay in Greve in Chianti
Typical Tuscan country house
4.99 out of 5 average rating, 427 reviews, 2 bedrooms, 2 beds, 2 bathrooms
22–27 Nov
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
4.94 out of 5 average rating, 52 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Jul
Guest favourite
Farm stay in Radda in Chianti
1500 Stone house a corner of paradise in Chianti
4.91 out of 5 average rating, 68 reviews, 2 bedrooms, 3 beds, 2 bathrooms
4–9 Jul
Top guest favourite
Farm stay in Gaiole in Chianti
Le Rondini - where it all began
4.84 out of 5 average rating, 109 reviews, 2 bedrooms, 3 beds, 1 bathroom
11–16 Aug
Top guest favourite
Villa in Gaiole in Chianti
Sestuccina
4.93 out of 5 average rating, 43 reviews, 2 bedrooms, 2 beds, 2 bathrooms
31 Oct – 7 Nov
Top guest favourite
Apartment in Siena
Luxury Penthouse with a View of Piazza del Campo
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 3 beds, 4 bathrooms
21–26 Jul