filters

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
,
4.91 out of 5 average rating, 34 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
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
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
Villa in Gaiole in Chianti
Montemarcoli
Individual host
7–12 Nov
5.0 out of 5 average rating, 34 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
13–18 Sept
New place to stay
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 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
Home in Terranuova Bracciolini
Villa Piandarca - Tuscany - WIFI - private pool
Individual host
13–18 Sept
4.98 out of 5 average rating, 59 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
Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
27 Oct – 1 Nov
4.99 out of 5 average rating, 114 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
Home in Gaiole in Chianti
Borgo di Gaiole – Stylish Home in Chianti
Individual host
19–24 Oct
Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
Business host
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Apartment in Gaiole in Chianti
Casa BD, Vacation house with a view & travel guide
Business host
16–21 Sept
4.91 out of 5 average rating, 11 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, 18 reviews