Ossaia Holiday Rentals

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Holiday Rentals in Ossaia

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (155)
"Beyond the peace and tranquility offered by the setting, it truly felt like the guests’ wellbeing was prioritized- the spaces (I viewed three before making a decision) were clean and orderly, the staff was incredibly attentive, the restaurant was enjoyable, and the overall experience was a very positive one."
The price is AU$124
includes taxes & fees
13 Mar - 14 Mar
Abbadia Sicille Relais

Il Tosco

10.0 out of 10, Exceptional, (103)
"Wonderful total experience! Kind and generous service, available but not intrusive, perfect morning breakfast, beautiful linens in rooms and breakfast area. One couldn’t ask for more from hostess and owners! "
The price is AU$467
includes taxes & fees
31 Mar - 1 Apr
Il Tosco

Residenza Fabroni

8.8 out of 10, Excellent, (80)
"This is a very large apartment in a 500 year old well maintained building. It is in the beautiful historic area. Do be aware that this is a VERY hilly area and you will have to walk up and down steep streets everywhere you go. That includes from the parking area. Cars are restricted from the area around the apartment without a permit. "
The price is AU$163
includes taxes & fees
4 Mar - 5 Mar
Residenza Fabroni

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

10.0 out of 10, Exceptional, (113)
"Centrally located. One hour from all the great Tuscan towns, absolutely beautiful apartment and grounds! This is our second time here and we have loved it both times! Hope to return again!"
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)

Traditional stone cottage in rural, tranquil and quiet location built in 1799

9.8 out of 10, Exceptional, (39)
"John & Dianne were utterly lovely and made every effort for us. The listing is very clear and if you're looking for peace and quiet in a serene valley, you couldn't do better. The track should be driven with care but after the first time accompanied by John, it's not too bad. I wouldn't bring a car with low clearance though. John and Dianne are in their home next door which was nice to know. They very much left us to it and didn't mind us playing our music by the pool. Otherwise we didn't see...
Traditional stone cottage in rural, tranquil and quiet location built in 1799

Osteria del Borgo

9.2 out of 10, Wonderful, (142)
"Communication with owner excellent. Was able to drop bags at unit and then park car in space provided by hotel about a 10 minute walk down or up depending on direction. Apartment large and comfortable. Breakfast nice continental assortment. Owner helped with bags up 2 flights of stairs checking in. Excellent location. Every thing nearby. We would book again"
Osteria del Borgo

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

9.8 out of 10, Exceptional, (66)
"The views from this house are fantastic! And the location is perfect - steps from the old town of Montepulciano. Communication with Erika, the host was great. She prepared us with lots of details and recommendations for things to do nearby. We had some questions during our stay and Erika was very responsive. There is so much to do in the area - I almost wished we had more time to hang out on the beautiful terraces!"
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Farmhouse in the hills with panoramic view and swimming pool

9.6 out of 10, Exceptional, (67)
"Was wonderful and beautiful. "
Farmhouse in the hills with panoramic view and swimming pool

House / Villa - Monte San Savino

9.8 out of 10, Exceptional, (16)
"Es erwartet dich ein hübsches Häuschen mitten in der Natur. Etwas abgelegen, wir mochten es genau so. Natur und Ruhe pur. Die Inneneinrichtung ist schon etwas in die Jahre gekommen, aber es ist alles da was man braucht. "
House / Villa - Monte San Savino

House with garden and panoramic view over Lake Trasimeno

9.8 out of 10, Exceptional, (43)
"Beautiful location, very handy for the lake (swimming, pedelos etc) and with some lovely restaurants and gelatos in the local town! Views from the property are amazing, it is very quiet and peaceful"
House with garden and panoramic view over Lake Trasimeno

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (48)
"We received a warm welcome from the family and a thorough explanation of the facilities, the surrounding area and places of interest. Fabrizio communicated easily with us using the translation phone app. The apartment is very clean, well equipped and offers a genuine Italian experience. Simply wonderful."
The price is AU$286
includes taxes & fees
1 Mar - 2 Mar
Il Poggio dell'Eremita

Stone house - charming country villa in Tuscany

Stone house - charming country villa in Tuscany

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

8.2 out of 10, Very good, (42)
"We had a great stay at Massimo place. The grounds and pool were great! The views were to die for, and we had a different sun set every night! Thanks for the great stay Massimo! Will definitely back if in the area."
Villa with swimming pool and garden- San Feliciano, Trasimeno lake

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

9.8 out of 10, Exceptional, (64)
"Property is perfect for the view and the loction"
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

Villa Graziella, Romantic Perugia

9.0 out of 10, Wonderful, (2)
"Immobile attrezzato molto bene, ampi spazi esterni ed un'ottima comunicazione con il proprietario. Perfetta sia in un periodo invernale che estivo"
The price is AU$301
includes taxes & fees
1 Mar - 2 Mar
Villa Graziella, Romantic Perugia

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

9.4 out of 10, Exceptional, (40)
"Great time with friends! Can't beat the location and the hosts were amazing and responsive."
Villa with private pool, air conditioning near wineries at 3km from village

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

9.6 out of 10, Exceptional, (38)
"My wife and I had a wonderful stay in this great little apartment. It is clean and comfortable for two people. We loved being able to cook at home for a change after traveling for the past month. We were able to buy fresh pasta from the market down the road so that was perfect. The host was fantastic with communication and made an excellent dinner recommendation which is literally next door. Finally the view from the kitchen is gorgeous! It’s great to be able to open the window in the...
LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center

Casa Bacco - private house with a remarkable garden in the centre of Cortona

10.0 out of 10, Exceptional, (4)
"Our two adult children who were studying abroad met us here with our younger two children. We had two nights in a 12 day stay in Italy. Of all our stops, this was by far our favorite. The house was like a story book. The garden was so lovely, we spent an afternoon eating and sharing a bottle of wine. We were here in November and the weather was very mild compared to Chicago winters. Most of the stores and restaurants were open with far less people. We weren’t really here to see anything, we were...
Casa Bacco - private house with a remarkable garden in the centre of Cortona

beautiful tuscan villa with pool, ideal for groups

10.0 out of 10, Exceptional, (25)
"A wonderful property, submerged in beautiful natural surroundings, the flora and fauna were fantastic. Our whole family were delighted by the swifts, starlings and kestrels nesting at the property, my parents described the place as simply magical. Wonderful location for my Father's 80th birthday celebrations, John and Sabine are welcoming and warm hosts. We all felt very relaxed in this comfortable, spacious home. The outside is as well equipped as inside with lots of seating and a great pool...
beautiful tuscan villa with pool, ideal for groups

Heritage Tuscan Farmhouse with private swimming pool

10.0 out of 10, Exceptional, (44)
"We had a very happy stay at this house in the country with our two friends. It is ideally located within an hour’s drive of interesting sites and historic towns. The place and its surroundings allowed us a restful and pleasant respite from our busier daytrips. The house was comfortable, beds were very good and the garden provided a peaceful setting with a choice of sitting and lounging areas. Louise was lovely, an excellent hostess who responded quickly to our questions and needs. "
Heritage Tuscan Farmhouse with private swimming pool
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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Other types of properties in Ossaia you may be interested in

Albergo San Biagio

3.0 star property
8.6 out of 10, Excellent, (153)
"Lovely hotel in a convenient location for us to park. We opted to eat in the restaurant and it was delicious, same for breakfast, very good indeed and excellent value. Only stayed one night but we will definitely stay again. "
The price is AU$157
includes taxes & fees
7 Mar - 8 Mar
Albergo San Biagio

Precise Tale Poggio Alla Sala

5.0 star property
9.4 out of 10, Exceptional, (75)
"Everything and everyone was spot on. Driveway needs repair "
Precise Tale Poggio Alla Sala

Monastero di Cortona Hotel & Spa

5.0 star property
10.0 out of 10, Exceptional, (204)
"Super friendly service from most of the staff and beautiful property, restaurant and bars were great too. "
The price is AU$511
includes taxes & fees
27 Mar - 28 Mar
Monastero di Cortona Hotel & Spa
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.

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?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: This holiday home rental outside of Ossaia is located in the city centre, 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. It offers a terrace, a garden and a selection of books so that you can immerse yourself in your holiday.

How many holiday rentals are there in Ossaia?

With 7 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 Giuseppe Garibaldi Memorial and Villa Bramasole.

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.