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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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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 Bettolle
A Fairytale Wedding in Tuscany
Business host
1–6 Oct
5.0 out of 5 average rating, 27 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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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
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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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Top guest favourite
Flat in Cortona
Casa Ersilia Vacation
Individual host
1–6 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Casalini
Cottage surrounded by nature
Individual host
11–18 Oct
4.99 out of 5 average rating, 111 reviews
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Home in Cortona
Tower Garden
4 bedrooms, 4 queen beds, 4 bathrooms
4–9 Oct
5.0 out of 5 average rating, 4 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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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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Superhost
Farm stay in Tuoro sul Trasimeno
Casa di Giano – villa with outdoor hot tub, sleeps 6/8
Business host
19–24 Dec
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Top guest favourite
Flat in Camucia
Il Sasso Apartment
Individual host
9–14 Nov
4.96 out of 5 average rating, 69 reviews
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Guest favourite
Home in Cortona
Common chaffinch + Almond + Juniper
Individual host
8–13 Oct
5.0 out of 5 average rating, 13 reviews