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

Top guest favourite
Flat in Radda in Chianti
La Casina
1 bedroom, 2 beds, 1 private bathroom
8–13 Oct, Individual host
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4.93 out of 5 average rating, 118 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
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
Montemarcoli
Individual host
7–12 Nov
5.0 out of 5 average rating, 34 reviews
Flat in Radda in Chianti
Cottage
Individual host
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 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
Home in Lecchi
"La Casa di Maria Luce"® with panoramic terrace
Individual host
16–21 Sept
4.96 out of 5 average rating, 245 reviews
Home in Gaiole in Chianti
Borgo di Gaiole – Stylish Home in Chianti
Individual host
19–24 Oct
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
Guest favourite
Villa in Gaiole in Chianti
Corte del Chianti Dependance
Business host
15–20 Apr
5.0 out of 5 average rating, 6 reviews
Superhost
Apartment in Gaiole in Chianti
Casa Livio, a garden with a view
Business host
9–14 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
Business host
25–30 Oct
4.97 out of 5 average rating, 33 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Guest favourite
Villa in Castelnuovo dei Sabbioni
Villa Valdarno Chianti - Private Pool
Business host
26 Jun – 1 Jul
4.92 out of 5 average rating, 36 reviews
Guest favourite
Apartment in Greve in Chianti
Relax in a Chianti Classico winery
Business host
21–26 Sept
4.95 out of 5 average rating, 19 reviews
Guest favourite
Holiday home in Radda in Chianti
Pineta on La Spugna - oasis of peace & relaxation
Individual host
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Home in Tregole
Romantic villa in the Chianti Classico
Business host
12–17 Oct