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Search results; Over 1,000 homes in Monteriggioni

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Top guest favourite
Home in Monteriggioni
Poggiolo
2 bedrooms, 2 beds, 2 private bathrooms
8–13 Sept
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5.0 out of 5 average rating, 32 reviews
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Room in Monteriggioni
Rooms and Wine Monteriggioni, La prima
1 bed, 1 bathroom
1–6 Nov
4.87 out of 5 average rating, 15 reviews
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Home in Monteriggioni
Beautiful Villa with private swimming pool
2 bedrooms, 3 beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 18 reviews
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Home in Monteriggioni
The Barn Detached house surrounded by greenery
1 bedroom, 2 beds, 1 bathroom
3–8 Sept
5.0 out of 5 average rating, 12 reviews
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Villa in Monteriggioni
Tenuta Uzielli an elegant countryside villa
7 bedrooms, 7 beds, 8 bathrooms
1–6 May
5.0 out of 5 average rating, 20 reviews
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Flat in Monteriggioni
Osea Agritourism, Alba apartment
2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 49 reviews
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Barn in Monteriggioni
Charming Barn with Pool - Chianti Area
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 64 reviews
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Apartment in Colle di Val d'Elsa
Florence & Siena • Terrace • Private Parking • A/C
2 bedrooms, 3 beds, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 27 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay
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Flat in Poggibonsi
Laura Chianti Holidays
2 bedrooms, 5 beds, 2 bathrooms
9–14 Nov
4.98 out of 5 average rating, 338 reviews
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Apartment in Monteriggioni
Loggiato di Lorena - Along the Via Francigena
2 bedrooms, 2 double beds, 1.5 bathrooms
4–9 Sept
4.95 out of 5 average rating, 19 reviews
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Flat in Poggibonsi
App. Poggiarello
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.96 out of 5 average rating, 57 reviews
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Flat in Pievescola
TuscanView 360: 3 bedr, 2 baths, free parking
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.96 out of 5 average rating, 148 reviews
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Guest favourite
Apartment in Castellina Scalo
Da nonna Cri, apartment in Chianti
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.89 out of 5 average rating, 18 reviews
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Home in Colle di Val d'Elsa
Casa per la Costa – Colle di Val d'Elsa
1 bedroom, 2 beds, 1.5 bathrooms
1–6 Nov
4.96 out of 5 average rating, 289 reviews
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Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 31 reviews
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Superhost
Flat in Ampugnano
Villa Fausta Apartment
1 bedroom, 2 beds, 1.5 bathrooms
1–6 Sept
New place to stay
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Flat in Siena
[NEW!] Renovated, just a stone's throw from the center!
2 bedrooms, 4 beds, 2 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 19 reviews
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Home in Monteriggioni
Petraglia Farm by Interhome
9 bedrooms, 10 beds, 5 bathrooms
14–19 Sept