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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, 107 reviews
Guest favourite
Villa in Cortona
Agriturismo Henni panoramic pool sauna and jacuzzi
6 bedrooms, 7 beds, 7.5 bathrooms
19–26 Oct
4.94 out of 5 average rating, 49 reviews
Top guest favourite
Villa in Montepulciano
Wine Experience Villa in Montepulciano
4 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
4.97 out of 5 average rating, 123 reviews
Top guest favourite
Villa in Pergaccio
Villa Pergo is an ancient charming country villa
6 bedrooms, 11 beds, 3 bathrooms
6–11 Sept
5.0 out of 5 average rating, 65 reviews
Home in Cortona
Relais Tosca Slow and Rural Life
2 bedrooms, 2 double beds, 1 bathroom
8–13 Sept
Top guest favourite
Villa in Sarteano
Stone farmhouse in Val D'Orcia
5 bedrooms, 9 beds, 6 bathrooms
6–11 Sept
4.97 out of 5 average rating, 157 reviews
Superhost
Farm stay in Umbertide
Col delle Murce Farmhouse
3 bedrooms, 3 beds, 3 bathrooms
18–23 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Cortona
"Casa Elisa", house with swimming pool at the foot of Cortona
2 bedrooms, 4 beds, 2.5 bathrooms
2–7 Sept
4.97 out of 5 average rating, 71 reviews
Guest favourite
Serviced apartment in Cortona
Beautifully Restored 3 Bedroom Barn
3 bedrooms, 3 beds, 2 bathrooms
5–10 Sept
4.92 out of 5 average rating, 12 reviews
Top guest favourite
Farm stay in Monticchiello
Podere Lamino, Val d'Orcia, Pienza
4 bedrooms, 4 queen beds, 4 bathrooms
30 Oct – 4 Nov
4.99 out of 5 average rating, 67 reviews
Top guest favourite
Villa in Chianciano Terme
Charming Tuscan Villa with View forFamily&Friends
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.97 out of 5 average rating, 128 reviews
Top guest favourite
Flat in Cortona
Cortona Shabby Chic House - independent & balcony-
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 416 reviews
Villa in Montepulciano
Vineyard villa in Tuscany with private pool
10 bedrooms, 13 beds, 9 bathrooms
6–11 Oct
5.0 out of 5 average rating, 5 reviews
Home in Cortona
La Casa sul Vicolo Cortona Historic Center
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Flat in Montepulciano
A view from the gate, Montepulciano.
2 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
4.97 out of 5 average rating, 323 reviews
Top guest favourite
Apartment in Pienza
Casa rurale toscana in Mascagni Farmhouse Pienza
2 bedrooms, 2 double beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 158 reviews
Top guest favourite
Villa in Cortona
Stunning Tuscan Villa & Panoramic Infinity Pool
5 bedrooms, 8 beds, 4 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 95 reviews
Top guest favourite
Villa in Monte San Savino
Villa Tonacato - Charming Villa with private pool
4 bedrooms, 4 double beds, 4 bathrooms
31 Aug – 5 Sept
4.99 out of 5 average rating, 104 reviews
Guest favourite
Flat in Cortona
Luna Apartment
2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
4.98 out of 5 average rating, 53 reviews