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Search results; Over 1,000 homes in Monteriggioni

Guest favourite
Villa in Monteriggioni
Villa of the 2 Olive Trees (Abbadia Isola)
6 bedrooms, 12 beds, 4 private bathrooms
7–12 Oct, Individual host
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4.97 out of 5 average rating, 174 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
Home in Monteriggioni
The Barn Detached house surrounded by greenery
Individual host
16–21 Oct
5.0 out of 5 average rating, 12 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
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
Flat in Monteriggioni
Osea Agritourism, Alba apartment
Business host
13–18 Sept
5.0 out of 5 average rating, 49 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 Poggibonsi
Laura Chianti Holidays
Individual host
9–14 Nov
4.98 out of 5 average rating, 338 reviews
Top guest favourite
Flat in Staggia
Cozy Apt near Siena, Chianti WiFi A/C Free Parking
Individual host
28 Sept – 3 Oct
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Apartment in Monteriggioni
Loggiato di Lorena - Along the Via Francigena
Business host
7–12 Sept
4.95 out of 5 average rating, 19 reviews
Guest favourite
Flat in Staggia
The Optimist's House
Individual host
9–14 Oct
4.9 out of 5 average rating, 70 reviews
Home in Monteriggioni
Petraglia Farm by Interhome
Business host
14–19 Sept
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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, 84 reviews
Guest favourite
Farm stay in Siena
"Annarosa" Apartment on Chianti hills
Business host
8–13 Mar
4.87 out of 5 average rating, 55 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, 289 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
Flat in Castellina in Chianti
Edera
Business host
28 Oct – 2 Nov
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
Business host
10–15 Oct
4.98 out of 5 average rating, 47 reviews