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Search results; Over 1,000 homes in Cavriglia

Guest favourite
Tiny home in Cavriglia
Chalet at the gates of Chianti
2 bedrooms, 2 beds, 1 private bathroom
20–25 Jul
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4.91 out of 5 average rating, 67 reviews
Superhost
Home in Figline e Incisa Valdarno
Villa among our vineyards on the outskirts of Chianti
4 bedrooms, 6 beds, 4 bathrooms
13–18 Sept
New place to stay
Guest favourite
Villa in Castelnuovo dei Sabbioni
Villa Valdarno Chianti - Private Pool
8 bedrooms, 12 beds, 7.5 bathrooms
26 Jun – 1 Jul
4.92 out of 5 average rating, 36 reviews
Top guest favourite
Home in Terranuova Bracciolini
Villa Piandarca - Tuscany - WIFI - private pool
3 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
4.98 out of 5 average rating, 59 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
Guest favourite
Home in Gaiole in Chianti
Exclusive private villa with private pool
6 bedrooms, 9 beds, 6 bathrooms
18–23 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Farm stay in Cavriglia
La Ginestra – Former Tuscan barn on 2 levels
1 bedroom, 1 double bed, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 8 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
Flat in San Gusmè
Beautiful medieval village!!!
2 bedrooms, 3 beds, 2 bathrooms
30 Oct – 4 Nov
4.99 out of 5 average rating, 471 reviews
Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
4 bedrooms, 6 beds, 4 bathrooms
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 141 reviews
Superhost
Flat in Cavriglia
Basilico - Semplicità e relax in Toscana
1 bedroom, 3 beds, 1 bathroom
4–9 Oct
Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
3 bedrooms, 3 double beds, 3.5 bathrooms
27 Oct – 1 Nov
4.99 out of 5 average rating, 114 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
Top guest favourite
Flat in Rignano sull'Arno
VIRGO apartment
2 bedrooms, 2 double beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 26 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 Modine
Tuscan Villa with Private Jacuzzi & River
6 bedrooms, 7 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 51 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
Flat in Loro Ciuffenna
Farmhouse apartment
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 16 reviews