
Holiday rentals in Ossaia
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Ossaia
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Ossaia holiday rentals
Other great holiday rentals in Ossaia
Guest favourite

Home in Castelmuzio
4.98 out of 5 average rating, 40 reviewsCasa Ora d"Oro - Panoramic Views
Jason AllenRating, 5 stars2 weeks ago
first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!
Top guest favourite

Home in Monsigliolo
5 out of 5 average rating, 7 reviews[5 minutes from Cortona]The farmhouse of Cortona
denizRating, 5 stars1 month ago
Antonella was a great host, very quick response to our questions, always had positive communication with us. Her house was an extraordinary house, this stone house and antique items from the 1800s were a very nice experience for us. The house was very nice and in a quiet location. Antonella had provided us with everything we needed, gave us a lot of activities and local advice, what we were able to do from what she recommended really pleased us very much, it was nice advice. We would recommend this house to anyone who wants to spend a quiet Tuscan holiday. If we go back here, Antonella's house will be our choice again.
Guest favourite

Villa in Montepulciano
4.95 out of 5 average rating, 218 reviewsAmazing Tuscany Villa, FREE parking
StephenRating, 5 stars2 weeks ago
A super cute place to stay, while it was just outside of the main town of Montepulciano, it was very peaceful and lovely home with plenty of character. Pier Luigi was a gracious host and even gave us welcome and departing gifts. We loved our stay here, Thank you Pier for your hospitality.
Guest favourite

Home in Cortona
5 out of 5 average rating, 6 reviewsPalazzo Passerini, Luxury Townhouse, Cortona
KarenRating, 5 stars4 weeks ago
Wow!! The home is beyond beautiful and extremely tasteful decorated. From the upstairs bedroom, the view is incredible. My family loved every aspect of the home and we enjoyed spending time together in the spacious living room. It is in the heart of Cortona, so we were able walk everywhere. Special thanks to Marialena, as she ensured we had everything we needed and helped us arrange rides from and to the train station. We can’t wait to return to stay here again!

Home in Cortona
4.78 out of 5 average rating, 72 reviewsThe farmhouse of Leda, single family house
DanielRating, 5 stars8 months ago
Lorenzas villa is the perfect escape to Cortona. Set in the valley, its long, picturesque driveway leads you to a charming estate that is as fabulous as you’d imagine. Simplicity abounds in this Tuscan haven, complete with all you’d need for an extended stay such as mine. This is my second time renting the home for over a month and it will give you all the peaceful tranquility and zen vibes you may ever need. Close to Cortona for fantastic restaurant and sightseeing as well as local grocery stores to stock the home for your stay. To note: I his farmhouse has been in her family for generations and is delicate and simple, treat it with love as it holds so many special memories that exude from its walls. The farmhouse is located on the second story as the first story has not been renovated and remains locked. I hope to return again to finish my book. Thank you!
Guest favourite

Villa in Cortona
5 out of 5 average rating, 5 reviewsResidence 2 Luxury
MegRating, 5 stars2 weeks ago
Nice and spacious home, with simple and functional decor/furniture. comfortable beds, stocked kitchen ware, several bathrooms- definitely would recommend this place to someone looking for a quiet, lovely place to stay that's an easy drive from Cortona/Camucia and other Tuscan towns. We were a little disappointed the spa/gymn/hotel were out of service while we were there,but the pool was refreshing and nice to have in the afternoons. Thanks for a great stay!
Guest favourite

Home in Ossaia
4.97 out of 5 average rating, 95 reviews700 year old restored tuscan home
CorinneRating, 5 stars2 weeks ago
liesl’s home was such perfect stay for our time in cortona. it is just a short drive from the city. the home has such a wonderful view and the beds were comfortable. I would definitely come back again to visit!
Guest favourite

Home in Cortona
4.97 out of 5 average rating, 59 reviews"Casa Elisa", house with swimming pool at the foot of Cortona
DanielleRating, 5 stars1 month ago
The stay "Casa Elisa" was better than we expected. It is a large house with even a basement with sauna. The pool in the garden (with outdoor shower and toilet) and the house itself were sparkling clean. There was no dust or cobweb to be discovered (not even behind a closet that we moved to be able to reach an outlet). The view from the balcony was breathtaking and the surroundings were fantastic. You are so in towns such as Siena, Arezzo, Perugia and there is also a large lake nearby where we rented a boat for a day (recommended). In short, we can recommend everyone to book with Lorenzo. The communication with Lorenzo was also excellent, easy to reach via app and speaks good English. His father comes to check and clean the pool every day and his mother's day baked a delicious cake very sweetly.
Destinations to explore
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Lake Trasimeno
- Lake Bolsena
- Frasassi Caves
- Avignonesi Winery Fattoria Le Capezzine
- Santa Maria della Scala
- Basilica of St Francis
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Tenuta Le Velette
- Pubblico Palace
- Cantina Colle Ciocco
- Mount Subasio
- Cantina de' Ricci
- Castiglion del Bosco Winery
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Madonna del Latte
- Furlo Gorge Nature Reserve
- Cantina Contucci
- Abbey of Monte Oliveto Maggiore
- Casa Del Cioccolato Perugina
- Podere Il Cocco
- Ugolino Golf Club