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Search results; Over 1,000 homes in Monteriggioni

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Superhost
Home in Monteriggioni
Cottage La Vita for 6 with private pool in Siena
2 bedrooms, 4 beds, 2 private bathrooms
7–12 Sept, Individual host
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4.68 out of 5 average rating, 44 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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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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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
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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Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
1–6 Sept
5.0 out of 5 average rating, 4 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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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
5–10 Sept
New place to stay
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Top guest favourite
Home in Colle di Val d'Elsa
The House in the Alley – Colle di Val d'Elsa
Individual host
5–10 Nov
4.99 out of 5 average rating, 133 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
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
7–12 Sept
4.98 out of 5 average rating, 215 reviews
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Top guest favourite
Apartment in Noce
Historic 17th-century farmhouse in Chianti, Tuscany
Business host
25–30 Oct
5.0 out of 5 average rating, 218 reviews
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Top guest favourite
Barn in Castellina in Chianti
Cipressini 2 - pool and amazing views
Individual host
17–22 Nov
5.0 out of 5 average rating, 65 reviews
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Superhost
Room in Monteriggioni
B&B Il Poderino, Oil Mill Room
Business host
21–26 Oct
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Top guest favourite
Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
Business host
24–29 Oct
4.99 out of 5 average rating, 82 reviews
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Top guest favourite
Apartment in Monteriggioni
Loggiato di Lorena - Along the Via Francigena
Business host
4–9 Sept
4.95 out of 5 average rating, 19 reviews
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Superhost
Home in Barberino Tavarnelle
Exclusive Villa with Swimming Pool in the Chianti Classico Area
Business host
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
Business host
20–25 Oct
5.0 out of 5 average rating, 140 reviews
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Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
Business host
7–12 Oct
5.0 out of 5 average rating, 14 reviews