Ossaia Vacation Rentals from ￥14,289: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Ossaia?

Agriturismo Borgo Spagnoli : This vacation home rental near Ossaia is located in a regional park and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a coffee maker. Kick off your shoes and enjoy yourself with a rooftop terrace and a private yard.

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Vacation Rentals in Ossaia

"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing "

￥22,601 total

includes taxes & fees

Jul 21 - Jul 22

"We loved staying here. Absolutely great communication, super room, lots of dining options. Highly recommend this place."

￥16,410 total

includes taxes & fees

Jul 24 - Jul 25

"We‘ve spent two wonderful weeks with our two year old daughter and our dog. The house is beautifully located in the hills with no direct neighbours. The view is fantastic and we felt immediately at home in this beautiful house. We had a wonderful time and our hosts were just lovely. (We cannot say anything about the pool - except that it is huge - because we were there out of season in March when the pool was closed.)"

"The people here are authentic and welcoming! The building, rooms and facilities are gorgeous! One of our most beautiful stays in our many trips to Italy "

￥45,579 total

includes taxes & fees

Aug 3 - Aug 4

"This is a charming house in a small town outside Cortona. Easily located near all the things you would want to see in the area. The host treated us like family and had homemade treats and wine waiting for our arrival. The house is perfectly suited for 4 people to stay and had a lot of charm. If you are looking to escape the hustle of daily life and relax this is the perfect location. "

"Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular."

￥25,606 total

includes taxes & fees

Jul 21 - Jul 22

"Jacopo and his family were super friendly, the restaurant is the best in Montepulciano and the views are breathtaking. If we come back we will stay at Osteria del Borgo again without a doubt. "

￥23,184 total

includes taxes & fees

Jul 23 - Jul 24

Romantic Suite, 1 Queen Bed, Kitchen, Courtyard View (Torchio) | Private kitchen | Fridge, oven, stovetop, coffee/tea maker

"Hostess very kind and engaging. Had nice map of the area with suggested places to visit."

"Property is closing and looks like it. Very unfortunate, I was there 30 years ago with fond memories! Obviously I should have done more homework!! Very sad."

"We had five wonderful days in beautiful Toscana! Great atmosphere, wonderful location of the hotel and very reasonably priced. Eating at their restaurant was quite pricy however. Breakfast ok but excellent croissants and coffee! One of the reasons we picked this hotel was the laundry service which was advertised on hotels.com. No laundry service was available. "

￥17,547 total

includes taxes & fees

Jul 29 - Jul 30

"The location and accommodations are perfect for a family. Nestled in the Italian countryside providing easy access to the nearby renaissance villages, art and landscapes and the people of Italy. The accommodations that Mieke has provided will only put a smile on your face."

"This was our second year staying in same apartment. It was so easy and perfectly located, we did not want to risk another location. The hot water has challenges but once I messaged them, they were over in minutes to help. If you have a rental car, this could not be more perfect as the parking is adjacent to the home. Incredible location. Best view of our trip. "

"Hospitality of Sandro and his family is great. The house is unique and the partly private swiing pool super. In summer season airconditioning would be a welkome addition. "

￥49,482 total

includes taxes & fees

Aug 6 - Aug 7

"Warm; clean; comfortable; well-located to everything—including parking. Quiet street-level apt with great caffe-Pasticceria a stone’s throw from front door. We very much enjoyed our stay there for 1 wk."

"We love our stay st Ca de Santi. Everything was great and the property is really amazing. You feel the Tuscany atmosphere."

"we had a amazing time staying at this beautiful Villla. I highly recommend it to anyone!"

"We had a group of 11 stay and could not have loved our time more. The location was a great central spot to drive to different towns. We loved relaxing by the pools in the afternoons and our dinners al fresco. An incredible place to spend your vacation. "

"Rooms are magnificent "

￥34,715 total

includes taxes & fees

Jul 21 - Jul 22

"Great time with friends! Can't beat the location and the hosts were amazing and responsive."

"It was only for a week but living there was a pleasure. Nearby towns had lots of interesting places to visit and good restaurants. The house itself was well fitted especially the kitchen which suited self catering groups as there are no restaurants within walking distance for those who like to drink with their evening meal. We all enjoyed our stay."

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Top Ossaia Hotel Reviews

Hotel Villa Marsili

10/10 Excellent

"No other hotel in Cortona will do! "

Agriturismo La Sovana

10/10 Excellent

"Friendly staff and great food! We had a Saturday dinner on arrival (pricier than weekday dinners but the pici pasta and florentina steaks were delicious) which was really a wonderful experience. The breakfast was tasty. Staff were always friendly. The property is great for walking around and so picturesque. "

Find out more about Ossaia

Search for holiday rentals in Ossaia on Expedia! You can easily find your home rentals, villas, holiday apartments in Ossaia using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Ossaia?

Yes, you can find vacation rentals near top local attractions in Ossaia, or you can select a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Ossaia?

Agriturismo Borgo Spagnoli: This vacation home rental near Ossaia is located in a regional park and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a coffee maker. Kick off your shoes and enjoy yourself with a rooftop terrace and a private yard.

How many vacation rentals are there in Ossaia?

With 8 Expedia vacation rentals, you're sure to find just the right place for your Ossaia stay.

What’s there to see and do in Ossaia?

While exploring the area, visit family-friendly sights like Arezzo Equestrian Centre, or get outside and enjoy nature at Isola Maggiore. In the larger area, you’ll find Villa Bramasole and Piazza della Repubblica.

What’s a vacation rental in Ossaia like?

Vacation rentals are private properties where you can stay for a couple of days or more in Ossaia. Vacation rentals offer amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.

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Ossaia Vacation Rentals

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Vacation Rentals in Ossaia

Abbadia Sicille Relais

Residenza Fabroni

Farmhouse in the hills with panoramic view and swimming pool

Il Tosco

Casina in authentic Tuscany

Il Poggio dell'Eremita

Osteria del Borgo

Agriturismo Borgo Spagnoli

Castello di Modanella

Borgo Dolciano

Luxury Cortona view hilltop Villa

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

Villa Graziella, Romantic Perugia

Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)

Beautiful renovated stone villa - private pool,park,air conditioning,smart tv

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

Charming Villa with private pool between Pienza and Montepulciano

Delcorto Suites

Villa with private pool, air conditioning near wineries at 3km from village

PRIVATE TUSCAN VILLA - 3 HEATED SWIMMING POOL - WEDDINGS, EVENTS, JACUZZI, SAUNA

Top Ossaia Hotel Reviews

Hotel Villa Marsili

Monastero di Cortona Hotel & Spa

Villa di Piazzano - Small Luxury Hotel of the World

Il Falconiere - Relais e Chateaux

Agriturismo La Sovana

Precise Tale Poggio Alla Sala

Hotel Continentale

Hotel Villa Ricci

Albergo San Biagio

Find out more about Ossaia

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Frequently asked questions