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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
1–6 Nov
4.87 out of 5 average rating, 15 reviews
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Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
2 bedrooms, 3 beds
10–17 Oct
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
1 bedroom, 2 beds
3–8 Sept
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Villa in Monteriggioni
Tenuta Uzielli an elegant countryside villa
7 bedrooms, 7 beds
7–12 Sept
5.0 out of 5 average rating, 20 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds
5–10 Sept
New place to stay
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Top guest favourite
Barn in Monteriggioni
Charming Barn with Pool - Chianti Area
2 bedrooms, 3 beds
20–25 Sept
4.98 out of 5 average rating, 64 reviews
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Flat in Monteriggioni
Osea Agritourism, Alba apartment
2 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 49 reviews
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Guest favourite
Flat in Staggia
The Optimist's House
1 bedroom, 1 bed
9–14 Oct
4.9 out of 5 average rating, 70 reviews
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Top guest favourite
Apartment in Colle di Val d'Elsa
Florence & Siena • Terrace • Private Parking • A/C
2 bedrooms, 3 beds
19–24 Oct
5.0 out of 5 average rating, 27 reviews
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Top guest favourite
Apartment in Monteriggioni
Loggiato di Lorena - Along the Via Francigena
2 bedrooms, 2 double beds
4–9 Sept
4.95 out of 5 average rating, 19 reviews
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Top guest favourite
Flat in Siena
Charm and Comfort
3 bedrooms, 3 beds
2–7 Sept
5.0 out of 5 average rating, 43 reviews
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Guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
4 bedrooms, 4 beds
6–11 Sept
5.0 out of 5 average rating, 9 reviews
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Guest favourite
Apartment in Castellina Scalo
Da nonna Cri, apartment in Chianti
1 bedroom, 2 beds
6–11 Sept
4.89 out of 5 average rating, 18 reviews
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Flat in Pievescola
TuscanView 360: 3 bedr, 2 baths, free parking
3 bedrooms, 4 beds
1–6 Sept
4.96 out of 5 average rating, 148 reviews
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Top guest favourite
Flat in Poggibonsi
App. Poggiarello
2 bedrooms, 3 beds
7–12 Sept
4.96 out of 5 average rating, 57 reviews
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Superhost
Flat in Ampugnano
Villa Fausta Apartment
1 bedroom, 2 beds
1–6 Sept
New place to stay
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Top guest favourite
Apartment in Noce
Historic 17th-century farmhouse in Chianti, Tuscany
1 bedroom, 2 beds
25–30 Oct
5.0 out of 5 average rating, 218 reviews
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Home in Castel San Gimignano
Elegant private cottage Volterra–San Gimignano
1 bedroom, 2 beds
10–15 Nov
5.0 out of 5 average rating, 3 reviews