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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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Superhost
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
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
Villa in Impruneta
Exclusive Estate: Concierge service & heated pool
6 bedrooms, 6 beds, 7 bathrooms
4–9 Oct
4.99 out of 5 average rating, 146 reviews
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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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Top guest favourite
Apartment in Siena
Luxury Penthouse with a View of Piazza del Campo
3 bedrooms, 3 beds, 4 bathrooms
27 Oct – 1 Nov
5.0 out of 5 average rating, 23 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
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
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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Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
6 bedrooms, 7 beds, 6.5 bathrooms
20–25 Oct
4.98 out of 5 average rating, 61 reviews
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Top guest favourite
Villa in Bucine
Villa Petrea - Holidays and Weddings
8 bedrooms, 14 beds, 8 bathrooms
24–31 Oct
4.94 out of 5 average rating, 90 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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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, 115 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 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
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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Luxe
Home in Gaiole in Chianti
La Tuscia – Tuscan Estate, Boutique Villa
4 bedrooms, 4 king beds, 5 bathrooms
24–29 Oct
5.0 out of 5 average rating, 22 reviews