
Vacation rentals in Ossaia
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Top-rated vacation rentals in Ossaia
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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

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

Vacation home in Chianciano Terme
5 out of 5 average rating, 95 reviewsThe Eagle and the Olive Tree
PatrickRating, 5 stars2 weeks ago
We had the absolute pleasure of spending three unforgettable days at Paolo and Monica’s 800-year-old farmhouse — and it was hands down the best Airbnb experience we’ve ever had. The home itself is stunning: full of history, character, and comfort, with every amenity thoughtfully provided. Each morning, Paolo and Monica prepared a beautiful, fresh breakfast spread complete with homemade cakes and warm, delicious options that started our days off with so much care and joy. The hospitality was truly beyond compare — Paolo and Monica are salt-of-the-earth people with hearts of gold. One of the highlights of our stay was visiting with the many animals they lovingly care for. From eagles and owls to donkeys, horses, peacocks, ducks, and sheep — it felt like something out of a storybook. Monica’s passion for rescuing and training animals is inspiring, and added such a special, personal touch to the experience. Thier home is filled with beauty, warmth, and heart. Coming back soon! ❤️❤️❤️
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.

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

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 favorite

Farm stay in Cortona
4.91 out of 5 average rating, 35 reviewsPoggio Martino | Childfriendly Agriturismo
LovisaRating, 5 stars3 weeks ago
It’s a very nice place. Unfortunately we had bad weather so we couldn’t use the outdoor areas so much but it was very beautiful. Lots os flowers and roses, very well taken care of garden. Pretty view and a good apartment :)
Top guest favorite

Farm stay in Montepulciano
4.97 out of 5 average rating, 76 reviewsAgriturismo Via della Stella | Apartment Lecci
DehuiRating, 5 starstoday
This place was very nice and beautiful, the scenery was breathtaking and the views were great. Facilities were well kept and it was very peaceful. The animals were also cute. One of the best Airbnb’s I’ve ever been to.
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- 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