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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
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
Top guest favourite
Home in Castiglion Fiorentino
Villa with Private Pool in the Tuscan Countryside
3 bedrooms, 4 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Lucignano
Belvedere Antico [Tuscan pool and garden]
4 bedrooms, 5 beds, 3 bathrooms
5–10 Aug
4.98 out of 5 average rating, 47 reviews
Guest favourite
Serviced apartment in Cortona
Beautifully Restored 3 Bedroom Barn
3 bedrooms, 3 beds, 2 bathrooms
5–10 Sept
4.91 out of 5 average rating, 11 reviews
Home in Cortona
Relais Tosca Slow and Rural Life
2 bedrooms, 2 double beds, 1 bathroom
8–13 Sept
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 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
Home in Cortona
La Casa sul Vicolo Cortona Historic Center
2 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
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
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
Guest favourite
Home in Cortona
Old house in Tuscany
1 bedroom, 2 beds, 1 bathroom
15–20 Sept
4.94 out of 5 average rating, 66 reviews
Superhost
Farm stay in Umbertide
Col delle Murce Farmhouse
3 bedrooms, 3 beds, 3 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Villa in Bettolle
A Fairytale Wedding in Tuscany
9 bedrooms, 9 queen beds, 9.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 26 reviews
Guest favourite
Holiday home in Cortona
Arianna's winery
3 bedrooms, 4 beds, 3 bathrooms
6–11 Aug
4.9 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Arezzo
[Piazza Grande] Prestigious Apartment with a View
3 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Montalcino
Villa Cipressino
4 bedrooms, 5 beds, 5 bathrooms
13–18 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
Guest favourite
Flat in Cortona
Luna Apartment
2 bedrooms, 4 beds, 2 bathrooms
12–17 Aug
4.98 out of 5 average rating, 53 reviews