Ossaia Holiday Rentals

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Holiday Rentals in Ossaia

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (159)
"Great Historical location."
The price is AU$181
includes taxes & fees
22 Oct - 23 Oct
Abbadia Sicille Relais

Delcorto Suites

10.0 out of 10, Exceptional, (27)
"Exceptional service great building felt like a Medici!"
The price is AU$358
includes taxes & fees
29 Sept - 30 Sept
Delcorto Suites

Farmhouse in the hills with panoramic view and swimming pool

9.6 out of 10, Exceptional, (74)
"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.)"
Farmhouse in the hills with panoramic view and swimming pool

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

9.6 out of 10, Exceptional, (71)
"My husband and I loved our stay here! It was so close to town and the terrace was absolutely stunning. Would definitely stay here again! "
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

Il Tosco

10.0 out of 10, Exceptional, (112)
"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 "
The price is AU$598
includes taxes & fees
29 Sept - 30 Sept
Il Tosco

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

10.0 out of 10, Exceptional, (53)
"We had a very nice stay and a well organized pizza night in the villa. Glad to come again:) "
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

Residenza Fabroni

8.8 out of 10, Excellent, (90)
"We had a wonderful stay, the staff was extremely friendly and helpful. Restaurants and shops were right at our doorstep."
The price is AU$151
includes taxes & fees
9 Oct - 10 Oct
Residenza Fabroni

Borgo Dolciano

9.0 out of 10, Wonderful, (24)
"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. "
The price is AU$182
includes taxes & fees
30 Sept - 1 Oct
Borgo Dolciano

Villa Graziella, Romantic Perugia

9.6 out of 10, Exceptional, (7)
"Great place. Would stay here again."
The price is AU$304
includes taxes & fees
9 Oct - 10 Oct
Villa Graziella, Romantic Perugia

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (54)
"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."
The price is AU$274
includes taxes & fees
20 Oct - 21 Oct
Il Poggio dell'Eremita

Luxury Cortona view hilltop Villa

10.0 out of 10, Exceptional, (48)
"Perfect location for day trips covering so many of the hilltop towns. Perfect accommodation for a group of 12 friends as each bedroom has it’s own bathroom.Perfect Villa for relaxing at home coffee every morning, lying by the pool and dinner watching the incredible sunsets.Perfect hosts. Denise takes care of everything while you are at the villa including cooking us a wonderful dinner. Mieke answered all our questions prior to our arrival very promptly. She has set the villa up perfectly and...
Luxury Cortona view hilltop Villa

Castello di Modanella

7.8 out of 10, Good, (16)
"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."
Castello di Modanella

Camping Villaggio Cerquestra

3.0 star property
9.0 out of 10, Wonderful, (21)
"Staff molto cordiale e disponibile. "
The price is AU$108
includes taxes & fees
27 Sept - 28 Sept
Camping Villaggio Cerquestra

Charming House in the heart of Montepulciano

10.0 out of 10, Exceptional, (60)
"Close to down town, everything you need."
Charming House in the heart of Montepulciano

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

9.8 out of 10, Exceptional, (35)
"We love our stay st Ca de Santi. Everything was great and the property is really amazing. You feel the Tuscany atmosphere."
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv

PRIVATE VILLA WALKING DISTANCE, PRIVATE POOL AND JACUZZI

10.0 out of 10, Exceptional, (199)
"Overall a terrific stay, Alice was very responsive to our groups needs. Beautiful placeto stay. Would definitely consider a return trip. 5 starsThank you Alice"
PRIVATE VILLA WALKING DISTANCE, PRIVATE POOL AND JACUZZI

Casina in authentic Tuscany

9.8 out of 10, Exceptional, (68)
"My mom and I stayed at Casina del Bibo for four days. The location is perfect if you want to stay in a small village away from all of the hustle of the Tuscan hill towns. You will definitely need a car, though. We stayed in the upstairs apartment, which had two large rooms with king sized beds (and air conditioning, which was much needed!). The sitting room is cozy. There is a small kitchen that seems well equipped, although we didn't cook anything. Anna Maria and her daughter Lorella were very...
Casina in authentic Tuscany

Il Casale Di Manuele 12, Emma Villas

10.0 out of 10, Exceptional, (3)
"We loved this home - everything was perfect and it was easy to find and enjoy. I highly recommend the next time you are wanting to stay in Tuscany! "
Il Casale Di Manuele 12, Emma Villas

Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment

9.2 out of 10, Wonderful, (29)
"Family of 7 adults spent 1 week in beautiful secluded Tuscan farmhouse. Great location for visiting the region - Arezzo short drive. Florence Pisa approx. 1.5 hours. Beautiful hilltop villages, olive groves and vineyards. Quintessential Tuscany!"
Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment

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

10.0 out of 10, Exceptional, (132)
"This was the absolute best part of our time in Italy. This house is just amazing, and Stefano is the most generous and charming host. The house is clean, well provisioned, and has historic significance with modern comforts. What a treat to stay in this wonderful house that is close to everything. "
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ossaia Hotel Reviews

Find out more about Ossaia

Find out more about Ossaia

Everything you need to know about Ossaia holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ossaia holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ossaia holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Ossaia holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ossaia. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ossaia holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ossaia holiday rentals we have selected for you start as low as AU$108 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Ossaia rentals

At Expedia, we put the best Ossaia holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Ossaia rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ossaia holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ossaia. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Ossaia?

Yes, there are holiday rentals close to the most popular sights in Ossaia, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Ossaia has to offer?

Farmhouse in the hills with panoramic view and swimming pool: This holiday home rental outside of Ossaia is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Ossaia?

With 8 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Villa Bramasole and Piazza della Repubblica.

What’s a holiday rental in Ossaia like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ossaia. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for family trips.