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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, 29 reviews
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Superhost
Room in Gaiole in Chianti
Argentina. Welcome to our small village, L...
2 beds, 1 bathroom
14–19 Oct
4.95 out of 5 average rating, 20 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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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
Villa in Linari
Entire villa with private pool, stunning view!
6 bedrooms, 7 beds, 6.5 bathrooms
1–6 Sept
4.98 out of 5 average rating, 60 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
6–11 Sept
4.99 out of 5 average rating, 112 reviews
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Superhost
Home in Galenda
Casa Pernice · Chianti villa with private pool
3 bedrooms, 3 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 14 reviews
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Guest favourite
Home in Moncioni
Private Tuscan hilltop farmhouse with pool
5 bedrooms, 7 beds, 4 bathrooms
1–6 Sept
4.9 out of 5 average rating, 30 reviews
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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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Superhost
Apartment in Siena
Luxury Penthouse with a View of Piazza del Campo
3 bedrooms, 3 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Home in Terranuova Bracciolini
Villa Piandarca - Tuscany - WIFI - private pool
3 bedrooms, 5 beds, 3 bathrooms
12–17 Sept
4.98 out of 5 average rating, 56 reviews
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Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
3 bedrooms, 3 king beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 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
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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 Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
5 bedrooms, 5 double beds, 5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 33 reviews
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Superhost
Apartment in Gaiole in Chianti
Casa Livio, a garden with a view
2 bedrooms, 2 beds, 2 bathrooms
4–9 Sept
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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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
5–10 Sept
New place to stay