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

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
Flat in Radda in Chianti
Cottage
Individual host
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 reviews
Guest favourite
Villa in Radda in Chianti
The Horn
Business host
19–26 Sept
4.93 out of 5 average rating, 14 reviews
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
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
Guest favourite
Holiday home in Radda in Chianti
Pineta on La Spugna - oasis of peace & relaxation
Individual host
15–20 Sept
5.0 out of 5 average rating, 5 reviews
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
Top guest favourite
Villa in Gaiole in Chianti
Galendino
Business host
10–17 Oct
5.0 out of 5 average rating, 10 reviews
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
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
Superhost
Flat in Radda in Chianti
attic on the rooftops of Chianti
Individual host
4–9 Oct
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
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
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
Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
Individual host
29 Sept – 4 Oct
5.0 out of 5 average rating, 3 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
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
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