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

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Guest favourite
Farm stay in Radda in Chianti
Stone house in Chianti peace and nature with lake
2 bedrooms, 4 beds, 2 private bathrooms
21–26 Sept, Business host
,
4.93 out of 5 average rating, 60 reviews
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Flat in Radda in Chianti
Cottage
Individual host
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Villa in Radda in Chianti
The Horn
Business host
19–26 Sept
4.93 out of 5 average rating, 14 reviews
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Top guest favourite
Villa in Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
Business host
3–8 Oct
5.0 out of 5 average rating, 33 reviews
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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
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Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
Business host
26–31 Oct
4.99 out of 5 average rating, 69 reviews
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Guest favourite
Holiday home in Radda in Chianti
Pineta on La Spugna - oasis of peace & relaxation
Individual host
16–21 Sept
5.0 out of 5 average rating, 5 reviews
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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
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Top guest favourite
Villa in Gaiole in Chianti
Galendino
Business host
10–17 Oct
5.0 out of 5 average rating, 10 reviews
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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
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Superhost
Flat in Radda in Chianti
attic on the rooftops of Chianti
Individual host
4–9 Oct
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Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
Business host
16–21 Oct
4.98 out of 5 average rating, 47 reviews
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Top guest favourite
Flat in Greve in Chianti
BorgoHome, apartment in downtown Greve in Chianti
Individual host
12–17 Oct
4.94 out of 5 average rating, 54 reviews
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Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
Individual host
29 Sept – 4 Oct
5.0 out of 5 average rating, 3 reviews
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Home in Castellina in Chianti
Cignanbianco - Sunrise and Sunset by Interhome
Business host
15–22 Oct
4.75 out of 5 average rating, 4 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
16–21 Sept
New place to stay
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Top guest favourite
Apartment in Figline e Incisa Valdarno
[Beatrice's Dream] Luxury & Design Penthouse 5*
Individual host
9–14 Oct
4.98 out of 5 average rating, 89 reviews
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Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
Individual host
27 Oct – 1 Nov
4.95 out of 5 average rating, 57 reviews
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Top guest favourite
Home in Lecchi
"La Casa di Maria Luce"® with panoramic terrace
Individual host
24–29 Sept
4.96 out of 5 average rating, 245 reviews