Ossaia Holiday Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Ossaia

Il Tosco

10.0 out of 10, Exceptional, (111)
"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 NZ$508
includes taxes & fees
28 June - 29 June
Il Tosco

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (159)
"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing "
The price is NZ$265
includes taxes & fees
27 June - 28 June
Abbadia Sicille Relais

Casina in authentic Tuscany

9.8 out of 10, Exceptional, (62)
"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. "
Casina in authentic Tuscany

Villa with swimming pool and garden- San Feliciano, Trasimeno lake

8.2 out of 10, Very good, (42)
"Gemäß der Anzeige und den schönen Fotos im Netz hatten wir einen super Plan – „unser Ferienhaus“ in Umbrien - eine Woche Umbrien erkunden, eine Woche am Pool genießen und eine Woche arbeiten…tja, dieser Plan ist eklatant gescheitert. Es wird kein Ferienhaus vermietet sondern ein Apartment im Erdgeschoss in einem bewohnten Haus mit einer älteren Frau, die nur italienisch spricht samt Hund und mind. vier Katzen sowie ständigen Besuchern; wir waren nie alleine und es war ständig laut. Das...
Villa with swimming pool and garden- San Feliciano, Trasimeno lake

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (52)
"Our family of 4 had such a beautiful time at this gorgeous villa. We only stayed for 2 nights, wish we stayed longer. Highly recommend!"
The price is NZ$286
includes taxes & fees
10 July - 11 July
Il Poggio dell'Eremita

Delcorto Suites

10.0 out of 10, Exceptional, (21)
"Rooms are magnificent "
The price is NZ$387
includes taxes & fees
27 June - 28 June
Delcorto Suites

Osteria del Borgo

9.2 out of 10, Wonderful, (145)
"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. "
Osteria del Borgo

Farmhouse in the hills with panoramic view and swimming pool

9.6 out of 10, Exceptional, (69)
"Thanks for a good time in your House!"
Farmhouse in the hills with panoramic view and swimming pool

Camping Villaggio Cerquestra

3.0 star property
9.0 out of 10, Wonderful, (21)
"Staff molto cordiale e disponibile. "
Camping Villaggio Cerquestra

Residenza Fabroni

8.8 out of 10, Excellent, (85)
"We loved staying here. Absolutely great communication, super room, lots of dining options. Highly recommend this place."
The price is NZ$177
includes taxes & fees
1 July - 2 July
Residenza Fabroni

Exclusive hideaway nestled in woods with stunning lakeview Tuscany/Umbria border

10.0 out of 10, Exceptional, (100)
"We had a wonderful Christmas time in the tranquil Italian Countryside. Coming from the buzzing city, this place was exactly what we were looking for. Calm, cozy and big enough to host the family for a short week away.The house offers enough space for up to 8 adults, which each couple having their own bathroom. Everything is exceptionally clean and the house is WELL equipped for cooking, and surviving in general.The owner keeps you in close coordination over the days to ensure your satisfaction....
Exclusive hideaway nestled in woods with stunning lakeview Tuscany/Umbria border

Luxury Cortona view hilltop Villa

10.0 out of 10, Exceptional, (47)
"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."
Luxury Cortona view hilltop Villa

Villa Graziella, Romantic Perugia

9.6 out of 10, Exceptional, (5)
"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. "
The price is NZ$443
includes taxes & fees
27 June - 28 June
Villa Graziella, Romantic Perugia

Borgo Dolciano

9.2 out of 10, Wonderful, (23)
"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 NZ$206
includes taxes & fees
27 June - 28 June
Borgo Dolciano

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

9.4 out of 10, Exceptional, (3)
"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."
PRIVATE TUSCAN VILLA - 3 HEATED SWIMMING POOL - WEDDINGS, EVENTS, JACUZZI, SAUNA

LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center

9.6 out of 10, Exceptional, (47)
"Property was in an amazing location. Kitchen view was spectacular. Walking distance to every main attraction. "
LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center

PRIVATE VILLA WALKING DISTANCE, PRIVATE POOL AND JACUZZI

10.0 out of 10, Exceptional, (197)
"In summary, a brilliant villa, perfect for our large group of families (4 couples with multiple kids). Citta della Pieve is a lovely town and there are loads of places to.visit nearby. We had a great time abd the hosts were very helpful. Would highly recommend."
PRIVATE VILLA WALKING DISTANCE, PRIVATE POOL AND JACUZZI

Villa with wonderful view of Lake Trasimeno and large panoramic swimming pool

10.0 out of 10, Exceptional, (4)
"Amazing property with wonderful view of Lake Trasimino , 7 bedroom, 8 bathrooms, swimming pool, outside dining, great kitchen and several living rooms all with air conditioning. Shower gel annd tissues etc all provided. Adequately close to supermarkets. Sun beds were a bit tired/ broken."
Villa with wonderful view of Lake Trasimeno and large panoramic swimming pool

Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo

10.0 out of 10, Exceptional, (15)
"This worked out really well for our extended family across 3 generations. Lots of space, great amenities, and we loved Arezzo. Liliana is a brilliant host"
Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo

Charming House in the heart of Montepulciano

10.0 out of 10, Exceptional, (58)
"Close to down town, everything you need."
Charming House in the heart of Montepulciano
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Villa with swimming pool and garden- San Feliciano, Trasimeno lake: This holiday home rental outside of Ossaia is located in a rural location, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a pool table and 1 hot tub.

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.