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Search results; Over 1,000 homes in Monteriggioni

Guest favourite
Home in Monteriggioni
Romantic panoramic farmhouse near Siena
1 bedroom, 1 bed, 1 private bathroom
21–26 Oct
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4.92 out of 5 average rating, 38 reviews
Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
2 bedrooms, 3 beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 18 reviews
Guest favourite
Room in Monteriggioni
Rooms and Wine Monteriggioni, Il chianti
1 double bed, 1 bathroom
3–8 Nov
5.0 out of 5 average rating, 42 reviews
Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
1 bedroom, 2 beds, 1 bathroom
16–21 Oct
5.0 out of 5 average rating, 14 reviews
Home in Monteriggioni
Below the Monteriggioni Walls
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
Guest favourite
Home in Monteriggioni
Next to castle of Villa-Siena. heart Francigena
4 bedrooms, 8 beds, 2 bathrooms
14–19 Sept
4.83 out of 5 average rating, 157 reviews
Top guest favourite
Barn in Monteriggioni
Charming Barn with Pool - Chianti Area
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Villa in Monteriggioni
Tenuta Uzielli an elegant countryside villa
7 bedrooms, 7 beds, 8 bathrooms
1–6 May
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Flat in Monteriggioni
Osea Agritourism, Alba apartment
2 bedrooms, 4 beds, 1 bathroom
8–13 Oct
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Gavignano
Poggio Massiccioli
2 bedrooms, 2 queen beds, 1 bathroom
30 Oct – 4 Nov
4.92 out of 5 average rating, 388 reviews
Top guest favourite
Flat in Poggibonsi
Laura Chianti Holidays
2 bedrooms, 5 beds, 2 bathrooms
9–14 Nov
4.98 out of 5 average rating, 340 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds, 2 bathrooms
16–21 Oct
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Home in Pievescola
Borgo Ripostena – No. 8 Casa Vecchia
2 bedrooms, 3 beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 201 reviews
Top guest favourite
Flat in Siena
[NEW!] Renovated, just a stone's throw from the center!
2 bedrooms, 4 beds, 2 bathrooms
5–10 Nov
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Apartment in Colle di Val d'Elsa
Florence & Siena • Terrace • Private Parking • A/C
2 bedrooms, 3 beds, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 29 reviews
Flat in Pievescola
TuscanView 360: 3 bedr, 2 baths, free parking
3 bedrooms, 4 beds, 2 bathrooms
9–14 Oct
4.96 out of 5 average rating, 148 reviews
Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms, 3 beds, 2.5 bathrooms
29 Oct – 3 Nov
4.98 out of 5 average rating, 87 reviews
Top guest favourite
Flat in Castellina in Chianti
La dolce vita in Chianti. Pool and Relaxation
2 bedrooms, 3 beds, 1 bathroom
8–13 Oct
4.85 out of 5 average rating, 354 reviews