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Search results; Over 1,000 homes in Monteriggioni

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Guest favourite
Villa in Monteriggioni
Villa of the 2 Olive Trees (Abbadia Isola)
6 bedrooms, 12 beds, 4 private bathrooms
7–12 Oct, Individual host
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4.97 out of 5 average rating, 174 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, 18 reviews
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Home in Monteriggioni
Under the Walls of Monteriggioni
Individual host
4–9 Oct
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Guest favourite
Room in Monteriggioni
Rooms and Wine Monteriggioni, Il chianti
Business host
3–8 Nov
5.0 out of 5 average rating, 42 reviews
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Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
Individual host
16–21 Oct
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Villa in Monteriggioni
Tenuta Uzielli an elegant countryside villa
Business host
1–6 May
5.0 out of 5 average rating, 20 reviews
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Home in Pievescola
La Casa di Gio - Tuscany in full view
Individual host
1–6 Oct
New place to stay
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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, 389 reviews
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Guest favourite
Home in Monteriggioni
Next to castle of Villa-Siena. heart Francigena
Individual host
10–15 Oct
4.84 out of 5 average rating, 158 reviews
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Top guest favourite
Flat in Monteriggioni
Osea Agritourism, Alba apartment
Business host
8–13 Oct
5.0 out of 5 average rating, 49 reviews
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Home in Monteriggioni
Petraglia Farm by Interhome
Business host
9–14 Oct
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Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
Business host
26–31 Oct
4.98 out of 5 average rating, 47 reviews
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Guest favourite
Dome in Volterra
Green Dome @ The Land Before Time Retreats
Business host
1–6 Oct
4.95 out of 5 average rating, 185 reviews
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Top guest favourite
Home in Poggiolo
Country House Podere l 'Assunta
Business host
27 Oct – 1 Nov
5.0 out of 5 average rating, 91 reviews
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Top guest favourite
Flat in Siena
Terrace on the walls of Siena - Casa Laura
Individual host
2–7 Jan
5.0 out of 5 average rating, 110 reviews
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Top guest favourite
Holiday home in San Gimignano
Margherita Tuscan home apartment
Business host
22–27 Nov
4.93 out of 5 average rating, 299 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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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
7–12 Oct
5.0 out of 5 average rating, 3 reviews
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Home in Castellina in Chianti
Cignanbianco - Sunrise and Sunset by Interhome
Business host
15–22 Oct
4.75 out of 5 average rating, 4 reviews