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Search results; Over 1,000 homes in Ossaia

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Guest favourite
Home in Ossaia
700 year old restored tuscan home
2 bedrooms, 2 beds, 2 private bathrooms
21–26 Nov
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4.94 out of 5 average rating, 109 reviews
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Villa in Cortona
Villa Ivana - Cortona - Tuscany
Business host
24–31 Oct
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Guest favourite
Villa in Cortona
Agriturismo Henni panoramic pool sauna and jacuzzi
Business host
19–26 Oct
4.94 out of 5 average rating, 51 reviews
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Top guest favourite
Villa in Cortona
Stunning Tuscan Villa & Panoramic Infinity Pool
Individual host
6–11 Oct
5.0 out of 5 average rating, 96 reviews
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Superhost
Farm stay in Cortona
Case Sant'Anna 18 beds
Business host
3–8 Oct
4.76 out of 5 average rating, 17 reviews
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Top guest favourite
Villa in Pergaccio
Villa Pergo is an ancient charming country villa
Business host
29 Apr – 4 May
5.0 out of 5 average rating, 66 reviews
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Top guest favourite
Villa in Cortona
Villa Il Giardino di Diana (12 people)
Business host
17–24 Oct
4.96 out of 5 average rating, 48 reviews
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Top guest favourite
Holiday home in Tuoro sul Trasimeno
the oasis of the foxes
Individual host
15–20 Nov
5.0 out of 5 average rating, 97 reviews
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Top guest favourite
Apartment in Tuoro sul Trasimeno
Foscolo's Apartment
Individual host
1–6 Oct
4.97 out of 5 average rating, 119 reviews
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Flat in Cortona
Melody House Cortona: your holiday in harmony
Individual host
6–11 Oct
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Villa in Pienza
Pennella | Private villa with panoramic pool
Business host
10–17 Oct
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Superhost
Villa in Cortoreggio
Farmhouse in Contea, Angelici Winery, private pool
Business host
1–8 Oct
4.93 out of 5 average rating, 15 reviews
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Top guest favourite
Farm stay in Monte San Savino
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
Business host
30 Oct – 4 Nov
4.99 out of 5 average rating, 116 reviews
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Top guest favourite
Home in Cortona
Relais Tosca Slow and Rural Life
Individual host
21–26 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in La Cima
House on the Meadow
Individual host
3–8 Oct
4.98 out of 5 average rating, 52 reviews
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Top guest favourite
Home in Cortona
Casa Vinalia: Etruscan paradise
2 bedrooms, 2 double beds, 2 bathrooms
14–19 Oct
4.93 out of 5 average rating, 89 reviews
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Top guest favourite
Villa in Montepulciano
Wine Experience Villa in Montepulciano
Business host
30 Oct – 4 Nov
4.97 out of 5 average rating, 126 reviews
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Top guest favourite
Villa in Monte San Savino
Villa Tonacato - Charming Villa with private pool
Individual host
11–16 Oct
4.99 out of 5 average rating, 109 reviews
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Guest favourite
Home in Cortona
Nello's, Villa with private SPA and pool
Business host
3–8 Oct
5.0 out of 5 average rating, 19 reviews