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Search results; Over 1,000 homes in Monsigliolo

Superhost
Home in Monsigliolo
18th-century farmhouse in Cortona, with a garden and 4 bathrooms
3 bedrooms, 4 beds, 4 private bathrooms
16–21 Oct
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4.87 out of 5 average rating, 30 reviews
Top guest favourite
Home in Cortona
"Casa Elisa", house with swimming pool at the foot of Cortona
2 bedrooms, 4 beds, 2.5 bathrooms
14–19 Sept
4.97 out of 5 average rating, 73 reviews
Top guest favourite
Farm stay in Camucia
The Garden of Olives | Casa Ippocastano
2 bedrooms, 2 beds, 2 bathrooms
14–19 Oct
5.0 out of 5 average rating, 26 reviews
Guest favourite
Farm stay in Camucia
The Garden of Olives | Casa Mimosa
1 bedroom, 1 bed, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Villa in Cortona
Stunning Tuscan Villa & Panoramic Infinity Pool
5 bedrooms, 8 beds, 4 bathrooms
6–11 Oct
5.0 out of 5 average rating, 96 reviews
Superhost
Villa in Cortona
Casa I Pini
4 bedrooms, 5 beds, 4 bathrooms
10–17 Oct
5.0 out of 5 average rating, 8 reviews
Home in Tavernelle
Podere Ponticelli – Villa overlooking Cortona
5 bedrooms, 6 beds, 6 bathrooms
16–21 Sept
Home in Cortona
Cornici di verde - Cortona
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Holiday home in Cortona
Tuscan Suite Amiata in Villa Q Dimorae Adults Only
2 bedrooms, 3 beds, 2.5 bathrooms
15–20 Sept
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Home in Castiglion Fiorentino
Villa with Private Pool in the Tuscan Countryside
3 bedrooms, 4 beds, 2 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Cortona
Nello's, Villa with private SPA and pool
10 bedrooms, 10 beds, 12 bathrooms
20–25 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Holiday home in Tuoro sul Trasimeno
the oasis of the foxes
2 bedrooms, 3 beds, 1 bathroom
10–15 Oct
5.0 out of 5 average rating, 97 reviews
Home in Cortona
Tower Garden
4 bedrooms, 4 queen beds, 4 bathrooms
14–19 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Farm stay in Cortona
Villa in Cortona , large garden, pool with a view
7 bedrooms, 10 beds, 5 bathrooms
3–10 Oct
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Castiglion Fiorentino
Hidden gem in Tuscany
3 bedrooms, 3 beds, 3 bathrooms
26–31 Oct
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Flat in Cortona
La Terrazza Cortonese in town center with terrace
2 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Cortona
Common chaffinch + Almond + Juniper
5 bedrooms, 6 beds, 5.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 12 reviews
Superhost
Farm stay in Cortona
Case Sant'Anna 18 beds
9 bedrooms, 12 beds, 8 bathrooms
3–8 Oct
4.76 out of 5 average rating, 17 reviews
Top guest favourite
Villa in Montepulciano
Full Estate in Montepulciano WiFi/Heated Pool incl
4 bedrooms, 5 beds, 4.5 bathrooms
19–26 Sept
5.0 out of 5 average rating, 27 reviews