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

Luxe
Villa in Radda in Chianti
Villa Montemaggio
3 bedrooms, 3 beds, 3 bathrooms
16–21 Sept, Business host
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4.91 out of 5 average rating, 33 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
19–26 Sept
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
Montemarcoli
Individual host
7–12 Nov
5.0 out of 5 average rating, 34 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
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
Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
7–12 Sept
4.99 out of 5 average rating, 114 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
6–11 Sept
New place to stay
Flat in Radda in Chianti
Cottage
Individual host
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
Business host
18–23 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Rignano sull'Arno
VIRGO apartment
Business host
20–25 Sept
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Terranuova Bracciolini
Villa Piandarca - Tuscany - WIFI - private pool
Individual host
12–17 Sept
4.98 out of 5 average rating, 58 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, 17 reviews
Top guest favourite
Farm stay in Monte San Savino
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
Business host
30 Oct – 4 Nov
4.99 out of 5 average rating, 114 reviews
Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
Business host
7–12 Sept
5.0 out of 5 average rating, 3 reviews
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