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Search results; Over 1,000 homes in Monsigliolo

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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
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Top guest favourite
Home in Cortona
"Casa Elisa", house with swimming pool at the foot of Cortona
2 bedrooms, 4 beds, 2.5 bathrooms
17–22 Sept
4.97 out of 5 average rating, 73 reviews
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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
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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
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Superhost
Farm stay in Camucia
Il Giardino degli Ulivi | Villa with private pool
9 bedrooms, 9 beds, 8 bathrooms
14–19 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Villa in Cortona
The Estate 1760 - Holiday in Cortona
10 bedrooms, 11 beds, 9.5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 6 reviews
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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
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Top guest favourite
Villa in Cortona
Villa Il Giardino di Diana (12 people)
6 bedrooms, 8 beds, 4 bathrooms
17–24 Oct
4.96 out of 5 average rating, 48 reviews
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Home in Tavernelle
Podere Ponticelli – Villa overlooking Cortona
5 bedrooms, 6 beds, 6 bathrooms
19–24 Sept
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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, 13 reviews
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Superhost
Villa in Cortona
Villa La Colombaia
7 bedrooms, 16 beds, 7 bathrooms
3–8 Dec
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Top guest favourite
Flat in Cortona
SIGNORELLI HOUSE
3 bedrooms, 3 double beds, 3 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Villa in Arezzo
Tuscany View - Villa Arianna
4 bedrooms, 6 beds, 3 bathrooms
10–16 Oct
4.99 out of 5 average rating, 122 reviews
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Top guest favourite
Villa in Bettolle
A Fairytale Wedding in Tuscany
9 bedrooms, 9 queen beds, 9.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 27 reviews
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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
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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
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Guest favourite
Villa in Petrignano
Restored Farmhouse & Cottage with AC, Pool & WIFI
6 bedrooms, 9 beds, 5 bathrooms
19–24 Sept
4.97 out of 5 average rating, 66 reviews
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Villa in Pienza
Pennella | Private villa with panoramic pool
4 bedrooms, 6 beds, 6 bathrooms
10–17 Oct
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Guest favourite
Home in Montepulciano
Spacious Tuscan Home – 2 Connected Apts, 4BR/4BA
4 bedrooms, 8 beds, 4 bathrooms
10–15 Nov
5.0 out of 5 average rating, 9 reviews