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Search results; Over 1,000 homes in Monteriggioni

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Guest favourite
Cottage in Monteriggioni
Countryside, 10 min from Siena
Studio, 2 beds, 1 private bathroom
1–6 Sept, Individual host
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4.84 out of 5 average rating, 287 reviews
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Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
Individual host
10–17 Oct
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Room in Monteriggioni
Rooms and Wine Monteriggioni, La prima
Business host
1–6 Nov
4.87 out of 5 average rating, 15 reviews
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Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
Individual host
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
Business host
7–12 Sept
5.0 out of 5 average rating, 20 reviews
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Guest favourite
Flat in Staggia
The Optimist's House
Individual host
9–14 Oct
4.9 out of 5 average rating, 70 reviews
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Guest favourite
Flat in Staggia
Cozy Apt near Siena, Chianti WiFi A/C Free Parking
Individual host
6–11 Sept
4.96 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Siena
the chestnut house
Individual host
5–10 Oct
4.97 out of 5 average rating, 37 reviews
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Top guest favourite
Flat in Monteriggioni
Osea Agritourism, Alba apartment
Business host
13–18 Sept
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Flat in Gavignano
Poggio Massiccioli
Individual host
30 Oct – 4 Nov
4.92 out of 5 average rating, 385 reviews
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Top guest favourite
Apartment in Colle di Val d'Elsa
Florence & Siena • Terrace • Private Parking • A/C
Individual host
19–24 Oct
5.0 out of 5 average rating, 27 reviews
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Home in Monteriggioni
Petraglia Farm by Interhome
Business host
14–19 Sept
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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Guest favourite
Apartment in Castellina Scalo
Da nonna Cri, apartment in Chianti
Individual host
6–11 Sept
4.89 out of 5 average rating, 18 reviews
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Guest favourite
Dome in Volterra
Green Dome @ The Land Before Time Retreats
Business host
11–16 Sept
4.95 out of 5 average rating, 160 reviews
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Apartment in Vivaia
Nature & relax in the Chianti countrysite
Individual host
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Flat in Colle di Val d'Elsa
Colle Hub - On the outskirts of the village
Individual host
10–15 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Poggiolo
Country House Podere l 'Assunta
Business host
2–7 Oct
5.0 out of 5 average rating, 88 reviews
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Top guest favourite
Home in Colle di Val d'Elsa
Casa per la Costa – Colle di Val d'Elsa
Individual host
1–6 Nov
4.96 out of 5 average rating, 288 reviews