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Search results; Over 1,000 homes in Montebenichi

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Superhost
Home in Montebenichi
The Montebenichi Dovecote
4 bedrooms, 4 beds, 2 private bathrooms
22–27 Oct
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4.71 out of 5 average rating, 35 reviews
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Guest favourite
Holiday home in Montebenichi
Agriturismo I Moraioli, Cantina apartment
1 bedroom, 1 bed, 1 bathroom
13–18 Nov
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Home in Montebenichi
[Little Escape] 4 Beds + Private Panoramic Pool
2 bedrooms, 2 double beds, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 74 reviews
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Superhost
Holiday home in Rosennano
HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL
2 bedrooms, 6 beds, 3 bathrooms
22–27 Sept
4.99 out of 5 average rating, 76 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, 469 reviews
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Guest favourite
Home in Montebenichi
Casa Gorizia Townhouse - Authentic Tuscany
1 bedroom, 2 beds, 1 bathroom
24–29 Sept
4.94 out of 5 average rating, 31 reviews
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Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
4 bedrooms, 6 beds, 4 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Farm stay in Gaiole in Chianti
Le Rondini - where it all began
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.84 out of 5 average rating, 109 reviews
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Home in Ambra
Villa in traumhafter Lage
3 bedrooms, 5 beds, 2 bathrooms
1–8 Sept
5.0 out of 5 average rating, 5 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
12–17 Oct
4.98 out of 5 average rating, 82 reviews
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Top guest favourite
Villa in Ambra
Chianti Villa in Tuscany near Siena and Arezzo
5 bedrooms, 6 beds, 4 bathrooms
22–27 Sept
4.99 out of 5 average rating, 148 reviews
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Top guest favourite
Farm stay in Greve in Chianti
Farmhouse in Chianti with Swimming Pool
2 bedrooms, 2 double beds, 2 bathrooms
29 Oct – 3 Nov
4.99 out of 5 average rating, 510 reviews
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Superhost
Home in Gaiole in Chianti
Villa Melina - new life for the barn
1 bedroom, 1 bed, 1 bathroom
16–21 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Farm stay in Greve in Chianti
Farmhouse with pool in Chianti
2 bedrooms, 2 double beds, 2 bathrooms
17–22 Nov
4.98 out of 5 average rating, 443 reviews
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Top guest favourite
Flat in Siena
Terrace on the walls of Siena - Casa Laura
2 bedrooms, 2 beds, 2 bathrooms
30 Nov – 5 Dec
5.0 out of 5 average rating, 104 reviews
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Home in Montebenichi
Tuscan Dreamtime
1 bedroom, 1 bed, 2 bathrooms
25 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
5–10 Sept
New place to stay
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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, 3 reviews
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Top guest favourite
Flat in San Gusmè
La Dimora del Luca
1 bedroom, 2 beds, 1 bathroom
6–11 Nov
4.98 out of 5 average rating, 169 reviews