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Search results; Over 1,000 homes in Ossaia

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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4.93 out of 5 average rating, 106 reviews
Top guest favourite
Villa in Cortona
Stunning Tuscan Villa & Panoramic Infinity Pool
5 bedrooms, 8 beds
20–25 Sept
5.0 out of 5 average rating, 95 reviews
Top guest favourite
Home in Castiglion Fiorentino
Villa with Private Pool in the Tuscan Countryside
3 bedrooms, 4 beds
5–10 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Villa in Sarteano
Stone farmhouse in Val D'Orcia
5 bedrooms, 9 beds
31 Oct – 5 Nov
4.97 out of 5 average rating, 156 reviews
Top guest favourite
Villa in Monte San Savino
Villa Tonacato - Charming Villa with private pool
4 bedrooms, 4 double beds
29 Sept – 4 Oct
4.99 out of 5 average rating, 101 reviews
Home in Cortona
Tower Garden
4 bedrooms, 4 queen beds
26–31 Aug
Top guest favourite
Farm stay in Monticchiello
Podere Lamino, Val d'Orcia, Pienza
4 bedrooms, 4 queen beds
30 Oct – 4 Nov
4.99 out of 5 average rating, 67 reviews
Guest favourite
Villa in Tuoro sul Trasimeno
Villa I Lecci
5 bedrooms, 10 beds
22–27 Aug
4.92 out of 5 average rating, 25 reviews
Home in Cortona
Relais Tosca Slow and Rural Life
2 bedrooms, 2 double beds
8–13 Sept
Top guest favourite
Apartment in Pienza
Mascagni Farmhouse in Val d'Orcia, Pienza
2 bedrooms, 2 double beds
30 Oct – 4 Nov
5.0 out of 5 average rating, 158 reviews
Top guest favourite
Farm stay in Cortona
Relaxing-unspoiled country place Il Monte...
2 bedrooms, 2 beds
23–28 Aug
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Montepulciano
Spacious Tuscan Home – 2 Connected Apts, 4BR/4BA
4 bedrooms, 8 beds
23–28 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Farm stay in Monte San Savino
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
6 bedrooms, 7 beds
30 Oct – 4 Nov
4.99 out of 5 average rating, 111 reviews
Top guest favourite
Flat in Montepulciano
A view from the gate, Montepulciano.
2 bedrooms, 3 beds
15–20 Nov
4.97 out of 5 average rating, 322 reviews
Top guest favourite
Home in Cortona
"Casa Elisa", house with swimming pool at the foot of Cortona
2 bedrooms, 4 beds
2–7 Sept
4.97 out of 5 average rating, 70 reviews
Guest favourite
Farm stay in Cortona
Villa Le Celle Agritourism
4 bedrooms, 5 beds
13–18 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Villa in La Cima
Villa Aurora
3 bedrooms, 3 double beds
26 Sept – 1 Oct
4.98 out of 5 average rating, 65 reviews
Top guest favourite
Flat in Cortona
The window on the Theater
2 bedrooms, 3 beds
25–30 Sept
4.98 out of 5 average rating, 61 reviews
Top guest favourite
Home in Tuoro sul Trasimeno
the oasis of the foxes
2 bedrooms, 3 beds
10–15 Oct
5.0 out of 5 average rating, 93 reviews