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Search results; Over 1,000 homes in Monteriggioni

Guest favourite
Home in Monteriggioni
Siena Countryside Colle Ciupi
3 bedrooms, 7 beds, 4 private bathrooms
21–26 Sept, Individual host
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4.9 out of 5 average rating, 217 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, 14 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
Home in Monteriggioni
Under the Walls of Monteriggioni
Individual host
13–18 Sept
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
8–13 Oct
5.0 out of 5 average rating, 49 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
Business host
16–21 Oct
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Home in Colle di Val d'Elsa
Casa per la Costa – Colle di Val d'Elsa
Individual host
1–6 Nov
4.96 out of 5 average rating, 290 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 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
Home in Monteriggioni
Petraglia Farm by Interhome
Business host
15–20 Sept
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Holiday home in San Gimignano
Margherita Tuscan home apartment
Business host
22–27 Nov
4.93 out of 5 average rating, 298 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, 87 reviews
Guest favourite
Apartment in Castellina Scalo
Da nonna Cri, apartment in Chianti
Individual host
20–25 Sept
4.89 out of 5 average rating, 18 reviews
Top guest favourite
Home in Castellina in Chianti
Capanna di Sotto by Interhome.
Business host
30 Sept – 5 Oct
5.0 out of 5 average rating, 9 reviews