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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
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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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 Radda in Chianti
Tuscan character, contemporary style and comfort
Business host
26–31 Oct
4.99 out of 5 average rating, 69 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 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
Home in Figline e Incisa Valdarno
Villa among our vineyards on the outskirts of Chianti
Business host
8–13 Sept
New place to stay
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
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
Villa in Montevarchi
Designer Villa with Private Garden & Jacuzzi
Business host
30 Sept – 5 Oct
5.0 out of 5 average rating, 3 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
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
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