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

Home in Castiglion Fiorentino
5 out of 5 average rating, 35 reviewsHidden gem in Tuscany
MitchellRating, 5 stars3 weeks ago
Where to start? I truly can't say enough good things about this property. It exceeded expectations in every way. From start to finish, our time here was a delight. Amanda was responsive, helpful, and accommodating. The location is remote, and a bit of adventure to get to, but Amanda had communicated that and we were prepared with the proper rental car that made it a breeze. The house is beautifully appointed, has every amenity, and lots of perfect spaces for both quiet moments and areas to gather with your group. The outdoor spaces and pool area are lovely, beautifully landscaped, and the views are spectacular. Book this place; you won't be sorry.
Top guest favorite

Villa in Cortona
5 out of 5 average rating, 75 reviewsStunning Tuscan Villa & Panoramic Infinity Pool
CherieRating, 5 stars1 week ago
Immaculate villa with plenty of space for everyone. Exceeded our expectations. Remote location best for people who have a car however peaceful and very close to drive into town in 10 minutes. Amazing restaurants nearby. Spectacular views. Beautiful pool area. Attentive friendly hosts. Especially beautiful Elmo the dog.
Top guest favorite

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.
Top guest favorite

Condo in Tuoro sul Trasimeno
5 out of 5 average rating, 47 reviewsIl Canale, large apartment in farmhouse
EnricoRating, 5 stars4 weeks ago
The place is great and great getaway to relax. Will highly suggest!! The oil was great.
Guest favorite

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 favorite

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 favorite

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!
Destinations to explore
- Florence Vacation rentals
- Pisa Vacation rentals
- Bologna Vacation rentals
- Rome Vacation rentals
- Francavilla al Mare Vacation rentals
- Pula Vacation rentals
- Rovinj Vacation rentals
- Venice Vacation rentals
- Agnone Vacation rentals
- Portofino Vacation rentals
- Riviera di Levante Vacation rentals
- Verona Vacation rentals
- 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
- Castiglion del Bosco Winery
- Mount Subasio
- Cantina Colle Ciocco
- Furlo Gorge Nature Reserve
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Cantina de' Ricci
- Madonna del Latte
- Cantina Contucci
- Abbey of Monte Oliveto Maggiore
- Podere Il Cocco
- Ugolino Golf Club
- Casa Del Cioccolato Perugina