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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
Villa in Cortona
Villa Ivana - Cortona - Tuscany
9 bedrooms, 10 beds, 12 bathrooms
29 Aug – 5 Sept
Home in Cortona
Relais Tosca Slow and Rural Life
2 bedrooms, 2 double beds, 1 bathroom
8–13 Sept
New place to stay
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, 111 reviews
Guest favourite
Farm stay in Cortona
Villa Le Celle Agritourism
4 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 16 reviews
Home in Laterina Pergine Valdarno
Slow down. Live Tuscany in your private Villa!
7 bedrooms, 7 beds, 4.5 bathrooms
5–10 Aug
Top guest favourite
Home in Pergognano
Vacation house Casa Tilia
5 bedrooms, 9 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Lucignano
Belvedere Antico [Tuscan pool and garden]
4 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Farm stay in Cortona
Relaxing-unspoiled country place La Loggia...
1 bedroom, 1 king bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Villa in Lisciano Niccone
Villa San Martino, on the Tuscany/ Umbria border
6 bedrooms, 7 beds, 4 bathrooms
12–17 Sept
4.89 out of 5 average rating, 56 reviews
Top guest favourite
Flat in Arezzo
[Piazza Grande] Prestigious Apartment with a View
3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Villa in Sodo
Country house in Cortona, Tuscany
5 bedrooms, 6 beds, 5.5 bathrooms
14–19 Aug
4.96 out of 5 average rating, 24 reviews
Villa in San Leo Bastia
Villa Vasciano - Private Pool & AirCo
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 reviews
Farm stay in Cortona
Colle degli ulivi by geco vacation rentals
7 bedrooms, 9 beds, 6 bathrooms
16–21 Aug
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Villa in Sarteano
Stone farmhouse in Val D'Orcia
5 bedrooms, 9 beds, 6 bathrooms
17–22 Sept
4.97 out of 5 average rating, 156 reviews
Top guest favourite
Flat in Cortona
Cortona’s Rooftop Nest
3 bedrooms, 3 beds, 1 bathroom
3–8 Aug
4.99 out of 5 average rating, 181 reviews
Top guest favourite
Villa in Ambra
Chianti Villa in Tuscany near Siena and Arezzo
5 bedrooms, 6 beds, 4 bathrooms
8–13 Oct
4.99 out of 5 average rating, 146 reviews
Top guest favourite
Villa in La Cima
Villa Aurora
3 bedrooms, 3 double beds, 3 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Villa in Arezzo
Casa Napoleone - Tuscan Villa w/ pool near Cortona
5 bedrooms, 6 beds, 4 bathrooms
16–23 Sept
4.96 out of 5 average rating, 24 reviews