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Search results; Over 1,000 homes in Monteriggioni

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Guest favourite
Home in Monteriggioni
Romantic panoramic farmhouse near Siena
1 bedroom, 1 bed, 1 private bathroom
21–26 Oct
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4.92 out of 5 average rating, 38 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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Room in Monteriggioni
Rooms and Wine Monteriggioni, Il chianti
1 double bed, 1 bathroom
3–8 Nov
5.0 out of 5 average rating, 42 reviews
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Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 33 reviews
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Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
1 bedroom, 2 beds, 1 bathroom
16–21 Oct
5.0 out of 5 average rating, 15 reviews
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Home in Monteriggioni
Below the Monteriggioni Walls
2 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
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Flat in Gavignano
Poggio Massiccioli
2 bedrooms, 2 queen beds, 1 bathroom
30 Oct – 4 Nov
4.92 out of 5 average rating, 389 reviews
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Apartment in Monteriggioni
Loggiato di Lorena - Along the Via Francigena
2 bedrooms, 2 double beds, 1.5 bathrooms
20–25 Sept
4.95 out of 5 average rating, 19 reviews
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Guest favourite
Home in Monteriggioni
Next to castle of Villa-Siena. heart Francigena
4 bedrooms, 8 beds, 2 bathrooms
20–25 Sept
4.83 out of 5 average rating, 157 reviews
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Farm stay in Poggibonsi
I Melograni del Chianti - Focolare Apartment
2 bedrooms, 3 beds, 2 bathrooms
27 Oct – 1 Nov
4.98 out of 5 average rating, 51 reviews
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Top guest favourite
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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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
16–21 Sept
New place to stay
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Flat in San Gimignano
Herons Superior Apartment - Splendid view!
2 bedrooms, 2 double beds, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 93 reviews
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Apartment in Noce
Historic 17th-century villa in Chianti, Tuscany
1 bedroom, 2 beds, 1 bathroom
11–16 Nov
5.0 out of 5 average rating, 222 reviews
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Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds, 2 bathrooms
16–21 Oct
4.98 out of 5 average rating, 47 reviews
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Home in Siena
the chestnut house
1 bedroom, 3 beds, 1 bathroom
5–10 Oct
4.97 out of 5 average rating, 39 reviews
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Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
2 bedrooms, 3 beds, 2 bathrooms
10–15 Oct
4.99 out of 5 average rating, 85 reviews
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Home in San Filippo a Ponzano
Infinity pool in Chianti 1
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 141 reviews
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Top guest favourite
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, 291 reviews