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Search results; Over 1,000 homes in Monteriggioni

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Superhost
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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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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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
1–6 Sept
New place to stay
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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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Guest favourite
Dome in Volterra
Green Dome @ The Land Before Time Retreats
Business host
2–7 Sept
4.95 out of 5 average rating, 160 reviews
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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
Flat in Poggibonsi
OLIVE TREE APARTMENT - CHIANTI
Individual host
1–6 Apr
4.97 out of 5 average rating, 279 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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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
Farm stay in Poggibonsi
I Melograni del Chianti - Apt. Mangiatoia 2BR
Business host
23–28 Oct
4.95 out of 5 average rating, 21 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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Superhost
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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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
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
Business host
24–29 Oct
5.0 out of 5 average rating, 15 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