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Search results; Over 1,000 homes in Monti

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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
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Home in Gaiole in Chianti
Villa Melina - new life for the barn
1 bedroom, 1 bed, 1 bathroom
10–15 Nov
5.0 out of 5 average rating, 3 reviews
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Superhost
Villa in Gaiole in Chianti
Le Granchiaie
4 bedrooms, 4 double beds, 5 bathrooms
17–24 Oct
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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, 474 reviews
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Room in Gaiole in Chianti
Argentina. Welcome to our small village, La .
2 beds, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 48 reviews
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Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms, 3 beds, 2.5 bathrooms
29 Oct – 3 Nov
4.98 out of 5 average rating, 87 reviews
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Cottage in Villa A Sesta
CASA MARIA
2 bedrooms, 3 beds, 3 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 47 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Farm stay in Greve in Chianti
Ancient Tuscan farmhouse in the Chianti hills
2 bedrooms, 2 double beds, 1 bathroom
23–28 Nov
4.99 out of 5 average rating, 284 reviews
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Flat in Siena
Relax a few steps from the Campo
2 bedrooms, 2 beds, 2 bathrooms
17–22 Oct
5.0 out of 5 average rating, 84 reviews
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Top guest favourite
Flat in Siena
San Francesco Penthouse
3 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 88 reviews
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Top guest favourite
Home in Troghi
Historic residence 30 minutes from Florence
2 bedrooms, 5 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 90 reviews
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Top guest favourite
Flat in Monteriggioni
Osea Agritourism, Alba apartment
2 bedrooms, 4 beds, 1 bathroom
8–13 Oct
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Farm stay in Monte San Savino
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
6 bedrooms, 7 beds, 7 bathrooms
30 Oct – 4 Nov
4.99 out of 5 average rating, 116 reviews
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Guest favourite
Flat in San Gusmè
La Dimora del Luca
1 bedroom, 2 beds, 1 bathroom
22–27 Oct
4.98 out of 5 average rating, 171 reviews
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Farm stay in Siena
Typical Tuscan Country House WITH A/C
1 bedroom, 1 double bed, 2 bathrooms
12–17 Oct
4.98 out of 5 average rating, 294 reviews
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Home in Santa Margherita-La Suvera
Apartment Immersed in Chianti
1 bedroom, 2 beds, 1 bathroom
22–27 Sept
5.0 out of 5 average rating, 19 reviews