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

Top guest favourite
Farm stay in Radda in Chianti
1500 Stone House in Chianti Heart private lake B
2 bedrooms, 3 beds, 1 private bathroom
23–28 Sept, Business host
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4.97 out of 5 average rating, 104 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
Flat in Radda in Chianti
Cottage
Individual host
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
Superhost
Home in Figline e Incisa Valdarno
Villa among our vineyards on the outskirts of Chianti
Business host
8–13 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
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
Villa in Greve in Chianti
Villa Le Pozzere
Business host
15–21 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Barberino Tavarnelle
Valluccia 51
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 49 reviews
Home in Gaiole in Chianti
Borgo di Gaiole – Stylish Home in Chianti
Individual host
19–24 Oct
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 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 San Filippo a Ponzano
Infinity pool in Chianti 1
Business host
20–25 Oct
5.0 out of 5 average rating, 141 reviews
Home in Castellina in Chianti
3 bedroom stone house on olive grove
Individual host
23–28 Sept
5.0 out of 5 average rating, 3 reviews
Villa in Montevarchi
Designer Villa with Private Garden & Jacuzzi
Business host
30 Sept – 5 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Holiday home in Rosennano
HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL
Business host
22–27 Sept
4.99 out of 5 average rating, 77 reviews