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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
Villa with pool in Chianti - Castellare Petroso
Business host
3–8 Oct
5.0 out of 5 average rating, 33 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 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
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 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
Guest favourite
Home in Moncioni
Private Tuscan hilltop farmhouse with pool
Individual host
19–24 Sept
4.9 out of 5 average rating, 30 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Superhost
Home in Figline e Incisa Valdarno
Villa among our vineyards on the outskirts of Chianti
Business host
14–19 Sept
New place to stay
Top guest favourite
Home in Terranuova Bracciolini
Villa Piandarca - Tuscany - WIFI - private pool
Individual host
25–30 Sept
4.98 out of 5 average rating, 59 reviews
Home in Gaiole in Chianti
Borgo di Gaiole – Stylish Home in Chianti
Individual host
19–24 Oct
Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
Individual host
2–7 Oct
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Florence
Villa Agnese · Pool · Duomo View · Parking
Individual host
24–29 Oct
5.0 out of 5 average rating, 19 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
Top guest favourite
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
Business host
27 Oct – 1 Nov
5.0 out of 5 average rating, 15 reviews
Flat in Radda in Chianti
Cottage
Individual host
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 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
Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
Individual host
18–23 Sept
4.98 out of 5 average rating, 60 reviews