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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
1–6 Oct
5.0 out of 5 average rating, 31 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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Top guest favourite
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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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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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
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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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Guest favourite
Home in Bagno A Ripoli
Historic Stone Villa | Pool | 15min Florence
7 bedrooms, 8 beds, 7 bathrooms
1–6 Oct
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Holiday home in Siena
New! Luxury Apartment in Historic Centre of Siena
3 bedrooms, 4 beds, 2 bathrooms
23–28 Oct
4.95 out of 5 average rating, 19 reviews
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Home in Fonterutoli
Private house overlooking Siena
6 bedrooms, 10 beds, 6 bathrooms
2–7 Nov
5.0 out of 5 average rating, 3 reviews
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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
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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, 88 reviews
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Superhost
Flat in Siena
Tiziana: Charming Stay on Winery Estate
3 bedrooms, 4 beds, 3 bathrooms
1–6 Oct
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Top guest favourite
Cottage in Villa A Sesta
CASA MARIA
2 bedrooms, 3 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 20 reviews
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Superhost
Flat in Bossi
Villino Ersilia Music, the charm of Chianti
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 4 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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Guest favourite
Villa in Gaiole in Chianti
Casa Faraona, villa with private pool
3 bedrooms, 4 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 32 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, 285 reviews