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

Guest favourite
Apartment in Radda in Chianti
💜 "Gaia" at Podere Le Fontanelle
1 bedroom, 2 beds, 1 private bathroom
20–25 Sept, Individual host
,
4.83 out of 5 average rating, 121 reviews
Guest favourite
Villa in Radda in Chianti
The Horn
Business host
19–26 Sept
4.93 out of 5 average rating, 14 reviews
Flat in Radda in Chianti
Cottage
Individual host
23–28 Sept
5.0 out of 5 average rating, 4 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
Holiday home in Radda in Chianti
Pineta on La Spugna - oasis of peace & relaxation
Individual host
12–17 Sept
5.0 out of 5 average rating, 5 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 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
Home in Galenda
Casa Pernice · Chianti villa with private pool
Business host
7–12 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Villa in Gaiole in Chianti
Galendino
Business host
10–17 Oct
5.0 out of 5 average rating, 10 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
Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
Individual host
29 Oct – 3 Nov
4.98 out of 5 average rating, 86 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Figline e Incisa Valdarno
[Fattoria degli Innocenti] Tuscany's Historic Gem
Business host
5–10 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
Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
Individual host
14–19 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Lecchi
"La Casa di Maria Luce"® with panoramic terrace
Individual host
16–21 Sept
4.96 out of 5 average rating, 244 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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Cottage in Villa A Sesta
CASA MARIA
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 20 reviews