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

Guest favourite
Home in Radda in Chianti
Villa le Scope 5*
3 bedrooms, 4 beds, 3 bathrooms
27 Sept – 2 Oct
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4.98 out of 5 average rating, 50 reviews
Guest favourite
Villa in Radda in Chianti
The Horn
5 bedrooms, 4 double beds, 3 bathrooms
19–26 Sept
4.93 out of 5 average rating, 14 reviews
Flat in Radda in Chianti
Cottage
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Villa in Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
5 bedrooms, 5 double beds, 5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
3 bedrooms, 4 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
5 bedrooms, 5 king beds, 5 bathrooms
26–31 Oct
4.99 out of 5 average rating, 69 reviews
Guest favourite
Home in Gaiole in Chianti
Exclusive private villa with private pool
6 bedrooms, 9 beds, 6 bathrooms
18–23 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Villa in Gaiole in Chianti
Galendino
2 bedrooms, 2 beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 10 reviews
Guest favourite
Holiday home in Radda in Chianti
Pineta on La Spugna - oasis of peace & relaxation
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
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, 2.5 bathrooms
29 Oct – 3 Nov
4.98 out of 5 average rating, 87 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay
Guest favourite
Flat in Figline e Incisa Valdarno
[Fattoria degli Innocenti] Tuscany's Historic Gem
2 bedrooms, 3 beds, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 30 reviews
Superhost
Flat in Radda in Chianti
attic on the rooftops of Chianti
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Top guest favourite
Apartment in Panzano in Chianti
Apt. Panzanello-Panzano in Chianti
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.96 out of 5 average rating, 281 reviews
Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds, 2 bathrooms
16–21 Oct
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
5 bedrooms, 1 bed, 5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 30 reviews
Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
6 bedrooms, 8 beds, 5 bathrooms
14–19 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cottage in Villa A Sesta
CASA MARIA
2 bedrooms, 3 beds, 3 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 20 reviews
Home in Castellina in Chianti
Cignanbianco - Sunrise and Sunset by Interhome
5 bedrooms, 3 single beds, 3 bathrooms
15–22 Oct
4.75 out of 5 average rating, 4 reviews