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

Guest favourite
Villa in Radda in Chianti
Fienile al Corno
3 bedrooms, 2 beds, 2 private bathrooms
23–28 Sept
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4.85 out of 5 average rating, 13 reviews
Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
5 bedrooms, 5 king beds, 5 bathrooms
26–31 Oct
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Villa in Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
5 bedrooms, 5 double beds, 5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Villa in Gaiole in Chianti
Galendino
2 bedrooms, 2 king beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
5 bedrooms, 1 bed, 5 bathrooms
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
3 bedrooms, 4 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 15 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay
Superhost
Home in Figline e Incisa Valdarno
Villa among our vineyards on the outskirts of Chianti
4 bedrooms, 6 beds, 4 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
2 bedrooms, 3 beds, 2 bathrooms
7–12 Nov
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
2 bedrooms, 3 beds, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Moncioni
Private Tuscan hilltop farmhouse with pool
5 bedrooms, 7 beds, 4 bathrooms
19–24 Sept
4.9 out of 5 average rating, 30 reviews
Flat in Radda in Chianti
Cottage
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
3 bedrooms, 5 beds, 2 bathrooms
21–26 Nov
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
2 bedrooms, 3 beds, 2 bathrooms
2–7 Oct
5.0 out of 5 average rating, 30 reviews
Luxe
Villa in Gaiole in Chianti
Le Pratola
7 bedrooms, 11 beds, 7.5 bathrooms
17–24 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Room in Gaiole in Chianti
Argentina. Welcome to our small village, L...
2 beds, 1 bathroom
26–31 Oct
4.95 out of 5 average rating, 22 reviews
Superhost
Flat in Bossi
Villino Ersilia Music, the charm of Chianti
2 bedrooms, 3 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
6 bedrooms, 7 beds, 6.5 bathrooms
18–23 Sept
4.98 out of 5 average rating, 60 reviews