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Search results; Over 1,000 homes in Monsigliolo

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Guest favourite
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, 31 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
14–19 Oct
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, 9 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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Guest favourite
Farm stay in Camucia
The Garden of Olives | Casa Mimosa
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Villa in Bettolle
A Fairytale Wedding in Tuscany
9 bedrooms, 9 queen beds, 9.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 27 reviews
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Guest favourite
Villa in Cortona
The Estate 1760 - Holiday in Cortona
10 bedrooms, 11 beds, 9.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 6 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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Guest favourite
Home in Cortona
Nello's, Villa with private SPA and pool
10 bedrooms, 10 beds, 12 bathrooms
3–8 Oct
5.0 out of 5 average rating, 19 reviews
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Superhost
Farm stay in Camucia
Il Giardino degli Ulivi | Villa with private pool
9 bedrooms, 9 beds, 8 bathrooms
25–30 Oct
5.0 out of 5 average rating, 3 reviews
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Flat in Cortona
Cortona Skyline Retreat
3 bedrooms, 4 beds, 2 bathrooms
28 Oct – 2 Nov
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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
Flat in Cortona
SIGNORELLI HOUSE
3 bedrooms, 3 double beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Cortona
Breathtaking views: Historic House w/Terrace & BBQ
3 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Castiglion Fiorentino
Holiday Home with Pool in Tuscany – La Roccia
2 bedrooms, 3 beds, 1 bathroom
13–18 Oct
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Farm stay in Montepulciano
Rural Tuscany | Farm stay, wining and dining
2 bedrooms, 2 queen beds, 2 bathrooms
29 Oct – 3 Nov
4.91 out of 5 average rating, 23 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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Top guest favourite
Farm stay in Monte San Savino
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
6 bedrooms, 7 beds, 7 bathrooms
30 Oct – 4 Nov
4.99 out of 5 average rating, 116 reviews
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Top guest favourite
Flat in San Gusmè
Beautiful medieval village!!!
2 bedrooms, 3 beds, 2 bathrooms
30 Oct – 4 Nov
4.99 out of 5 average rating, 474 reviews