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Search results; Over 1,000 homes in Monteriggioni

Top guest favourite
Home in Monteriggioni
Poggiolo
2 bedrooms, 2 beds, 2 private bathrooms
8–13 Nov
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5.0 out of 5 average rating, 33 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
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Flat in Siena
Terrace on the walls of Siena - Casa Laura
2 bedrooms, 2 beds, 2 bathrooms
8–13 Dec
5.0 out of 5 average rating, 108 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
Farm stay in Poggibonsi
I Melograni del Chianti - Focolare Apartment
2 bedrooms, 3 beds, 2 bathrooms
27 Oct – 1 Nov
4.98 out of 5 average rating, 51 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
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
Farm stay in Sovicille
House at Gianni - Leccio
2 bedrooms, 3 beds, 1 bathroom
29 Oct – 3 Nov
4.92 out of 5 average rating, 232 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
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
OLIVE TREE APARTMENT - CHIANTI
1 bedroom, 3 beds, 1 bathroom
1–6 Apr
4.98 out of 5 average rating, 280 reviews
Top guest favourite
Apartment in Monteriggioni
Loggiato di Lorena - Along the Via Francigena
2 bedrooms, 2 double beds, 1.5 bathrooms
20–25 Sept
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Holiday home in San Gimignano
Margherita Tuscan home apartment
2 bedrooms, 3 beds, 1 bathroom
22–27 Nov
4.93 out of 5 average rating, 298 reviews
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
Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
2 bedrooms, 3 beds, 2 bathrooms
10–15 Oct
4.99 out of 5 average rating, 85 reviews
Top guest favourite
Home in Colle di Val d'Elsa
Casa per la Costa – Colle di Val d'Elsa
1 bedroom, 2 beds, 1.5 bathrooms
1–6 Nov
4.96 out of 5 average rating, 290 reviews
Top guest favourite
Serviced apartment in Ancaiano
Tower house in the countryside with sensory shower
1 bedroom, 2 beds, 2 bathrooms
10–15 Nov
4.98 out of 5 average rating, 118 reviews