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Search results; Over 1,000 homes in Monteriggioni

Top guest favourite
Flat in Monteriggioni
Spacious Apartament
3 bedrooms, 3 beds, 2 private bathrooms
19–24 Oct, Individual host
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4.96 out of 5 average rating, 441 reviews
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
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
Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
Individual host
16–21 Oct
5.0 out of 5 average rating, 12 reviews
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
Top guest favourite
Barn in Monteriggioni
Charming Barn with Pool - Chianti Area
Individual host
20–25 Sept
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Flat in Gavignano
Poggio Massiccioli
Individual host
30 Oct – 4 Nov
4.92 out of 5 average rating, 386 reviews
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
Business host
25–30 Oct
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Flat in Monteriggioni
Osea Agritourism, Alba apartment
Business host
13–18 Sept
5.0 out of 5 average rating, 49 reviews
Home in Monteriggioni
Petraglia Farm by Interhome
Business host
14–19 Sept
Top guest favourite
Flat in San Gimignano
Herons Superior Apartment - Splendid view!
Business host
19–24 Sept
4.99 out of 5 average rating, 92 reviews
Top guest favourite
Home in Siena
Relay moderno a Siena
Individual host
18–23 Oct
4.98 out of 5 average rating, 124 reviews
Top guest favourite
Apartment in Colle di Val d'Elsa
Florence & Siena • Terrace • Private Parking • A/C
Individual host
27 Oct – 1 Nov
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
Individual host
29 Oct – 3 Nov
4.98 out of 5 average rating, 85 reviews
Guest favourite
Apartment in Castellina Scalo
Da nonna Cri, apartment in Chianti
Individual host
9–14 Sept
4.89 out of 5 average rating, 18 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Staggia
The Optimist's House
Individual host
9–14 Oct
4.9 out of 5 average rating, 70 reviews
Top guest favourite
Apartment in Monteriggioni
Loggiato di Lorena - Along the Via Francigena
Business host
20–25 Sept
4.95 out of 5 average rating, 19 reviews