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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, 473 reviews
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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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Top guest favourite
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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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
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
7–12 Oct
New place to stay
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Top guest favourite
Room in Gaiole in Chianti
Argenina. benvenuti nel nostro piccolo borgo, La .
1 double bed, 1 bathroom
18–23 Mar
4.97 out of 5 average rating, 35 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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Home in Siena
Siena Centre Luxury Design TownHouse -Parking Near
2 bedrooms, 2 double beds, 3 bathrooms
12–17 Oct
5.0 out of 5 average rating, 20 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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Top guest favourite
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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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
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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
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Top guest favourite
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
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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