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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
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
Superhost
Farm stay in Umbertide
Col delle Murce Farmhouse
3 bedrooms, 3 beds, 3 bathrooms
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Serviced apartment in Cortona
Medieval 2 Bedroom Barn in the nature
2 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
4.83 out of 5 average rating, 12 reviews
Top guest favourite
Home in Lucignano
Belvedere Antico [Tuscan pool and garden]
4 bedrooms, 5 beds, 3 bathrooms
16–21 Aug
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Place to stay in Cortona
Paola's Terrace
1 bedroom, 1 double bed, 1 bathroom
22–27 Aug
4.98 out of 5 average rating, 402 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
Home in Cortona
Relais Tosca Slow and Rural Life
2 bedrooms, 2 double beds, 1 bathroom
8–13 Sept
Top guest favourite
Apartment in Pienza
Mascagni Farmhouse in Val d'Orcia, 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 Sarteano
Stone farmhouse in Val D'Orcia
5 bedrooms, 9 beds, 6 bathrooms
17–22 Sept
4.97 out of 5 average rating, 157 reviews
Top guest favourite
Home in Cortona
Casa Primo Stylish-townhouse w/ patio & jetted tub
2 bedrooms, 2 double beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 75 reviews
Top guest favourite
Flat in Passignano sul Trasimeno
Sunset on the Lake – Passignano Centro Lake view
1 bedroom, 1 double bed, 1 bathroom
15–20 Oct
5.0 out of 5 average rating, 54 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, 102 reviews
Guest favourite
Serviced apartment in Cortona
Beautifully Restored 3 Bedroom Barn
3 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
4.92 out of 5 average rating, 12 reviews
Superhost
Villa in Cortona
Villa Dei Ciliegi
4 bedrooms, 6 beds, 3 bathrooms
17–24 Oct
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
Top guest favourite
Home in Montalcino
Villa Cipressino
4 bedrooms, 5 beds, 5 bathrooms
13–18 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Montepulciano
Spacious Tuscan Home – 2 Connected Apts, 4BR/4BA
4 bedrooms, 8 beds, 4 bathrooms
23–28 Aug
5.0 out of 5 average rating, 9 reviews
Home in Cortona
Tower Garden
4 bedrooms, 4 queen beds, 4 bathrooms
26–31 Aug