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Search results; Over 1,000 homes in Monteriggioni

Top guest favourite
Cottage in Monteriggioni
Monteriggioni Castello, holiday house in Tuscany
2 bedrooms, 7 beds, 1 private bathroom
1–6 Nov, Business host
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4.95 out of 5 average rating, 296 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, La prima
Business host
31 Oct – 5 Nov
4.87 out of 5 average rating, 15 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
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, 86 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
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
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
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
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 Poggibonsi
Laura Chianti Holidays
Individual host
9–14 Nov
4.98 out of 5 average rating, 340 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
Home in Poggiolo
Country House Podere l 'Assunta
Business host
27 Oct – 1 Nov
5.0 out of 5 average rating, 90 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 Siena
La Casina del Castagno
Individual host
5–10 Oct
4.97 out of 5 average rating, 38 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
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
Holiday home in Siena
New! Luxury Apartment in Historic Centre of Siena
3 bedrooms, 4 beds, 2 bathrooms
23–28 Oct
5.0 out of 5 average rating, 16 reviews