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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, 16 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 Cortona
Relais Tosca Slow and Rural Life
2 bedrooms, 2 double beds, 1 bathroom
8–13 Sept
Top guest favourite
Home in Lucignano
Belvedere Antico [Tuscan pool and garden]
4 bedrooms, 5 beds, 3 bathrooms
4–9 Aug
4.98 out of 5 average rating, 47 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
Villa in Tuoro sul Trasimeno
Villa I Lecci
5 bedrooms, 10 beds, 3 bathrooms
22–27 Aug
4.92 out of 5 average rating, 25 reviews
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
Top guest favourite
Flat in Arezzo
[Piazza Grande] Prestigious Apartment with a View
3 bedrooms, 3 beds, 2 bathrooms
4–9 Aug
5.0 out of 5 average rating, 9 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 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
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
Top guest favourite
Villa in Ambra
Chianti Villa in Tuscany near Siena and Arezzo
5 bedrooms, 6 beds, 4 bathrooms
22–27 Sept
4.99 out of 5 average rating, 146 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
Top guest favourite
Flat in Cortona
Cortona’s Rooftop Nest
3 bedrooms, 3 beds, 1 bathroom
6–11 Nov
4.99 out of 5 average rating, 181 reviews
Top guest favourite
Villa in Cortona
Stunning Tuscan Villa & Panoramic Infinity Pool
5 bedrooms, 8 beds, 4 bathrooms
20–25 Sept
5.0 out of 5 average rating, 95 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
Farm stay in San Quirico d'Orcia
Podere Pereti Nuovi – Modern Tuscan Villa
5 bedrooms, 5 double beds, 5.5 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 115 reviews