Search Holiday Rentals in Ossaia

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Dates

November 2026

December 2026

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Our top choices for Ossaia holiday rentals

1. Casale dell'Assiolo

Castiglione del Lago

Emma

includes taxes & fees

12 Nov - 13 Nov

A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.

2. B&B Piccolo Hotel

Cortona Old Town

mansoor

includes taxes & fees

5 Nov - 6 Nov

A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

3. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

Cortona Old Town

Joseph

includes taxes & fees

5 Nov - 6 Nov

4. iConic Wellness Resort

Arezzo

Wade

includes taxes & fees

2 Dec - 3 Dec

A park with picnic tables, a playground, and a gravel path.

5. Vacation home with a panoramic terrace, ideal for families and couples

Cortona

includes taxes & fees

5 Nov - 6 Nov

A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

6. CASA AMBRA

Cortona Old Town

includes taxes & fees

5 Nov - 6 Nov

A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

7. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

includes taxes & fees

7 Nov - 8 Nov

A rustic brick building with a mural, a clock, and various potted plants.

8. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casamaggiore

"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...

Anna

includes taxes & fees

5 Nov - 6 Nov

9. Montecchio di Cortona

Montecchio

Monica S.

includes taxes & fees

5 Nov - 6 Nov

10. San Michele al Borgo

Castiglion Fiorentino

Vern

includes taxes & fees

11 Nov - 12 Nov

A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

11. Vicolo Della Scala Rooms - La Luna

Cortona Old Town

includes taxes & fees

6 Nov - 7 Nov

A covered corridor with brick columns, potted plants, and a view of a lush landscape.

12. Abbadia Sicille Relais

Trequanda

Robert

includes taxes & fees

2 Dec - 3 Dec

A staircase with two lit lanterns on the wall.

13. Cortona Shabby Chic House<br>(Independent & Balcony)

Cortona Old Town

Erin

includes taxes & fees

5 Nov - 6 Nov

A spa area with a stone-walled arch, a hot tub, and a small window.

14. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

includes taxes & fees

9 Nov - 10 Nov

A balcony with a clear view of a distant landscape, a stone building, and a glass of orange juice.

15. Cortonas Rooftop Nest

Cortona Old Town

Robin F.

includes taxes & fees

8 Nov - 9 Nov

A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

16. Dolce Casa 2 by Tiny Away

Rigutino

includes taxes & fees

9 Nov - 10 Nov

A building with a stone facade, multiple windows, and a balcony.

17. Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

Cortona

Anonymous traveller

includes taxes & fees

11 Nov - 12 Nov

A stone building with a balcony, an archway, and potted plants.

18. Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

Cortona

Bonnie B.

includes taxes & fees

5 Nov - 6 Nov

An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

19. Fontelunga Hotel & Villas

Foiano della Chiana

Brian

20. Dolce Casa 1 by Tiny Away

Rigutino

includes taxes & fees

8 Nov - 9 Nov

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Find holiday rentals that suit your style

Top Ossaia Hotel Reviews

A terrace with sun loungers, stone walls, and potted plants.

Monastero di Cortona Hotel & Spa

Cortona Old Town

10/10 Excellent

What a beautiful hotel, the room was spacious clean and extremely well presented. All the staff were so friendly and helpful and made us feel so welcome. The breakfast was delicious and facilities great too. I loved the personal touches like the biscuits and water in the room with a note on arrival and also on the last day. We would highly recommend this hotel to anyone and thoroughly enjoyed our stay here!! :-)

Julie

A building with a stone pathway leading to an arched entrance, flanked by potted plants and lit by ground lights.

Hotel Villa Marsili

Cortona Old Town

10/10 Excellent

Marina and the team at Villa Marsili made our long weekend magical. They greeted us like long time friends visiting, my husband had never been previously to the hotel, but I had a few times before. He was blown away by the friendliness and warmth from ALL the team there. We treated ourselves to a Cookery Class with Ilaria and it was so much fun, and delicious! Breakfast was amazing, I said AMAZING! We have travelled all over the world and never ever have we had a breakfast this delicious, varied...

Edward

A panoramic view of a mountainous landscape with a valley, dense forest, and distant hills.

Locanda agli Amici

Cortona

10/10 Excellent

Our overall experience at this hotel has been amazing from start to finish, Silvia make us feel so welcome and went out of her way to make our stay one we will remember. At check in I mentioned I was gluten intolerance the next day at breakfast there was a homemade GF cake. So helpful with local information. Our room was spacious and the bathroom had an amazing shower all cleaned to a high standard. Beautiful pool and terrance area. We will be going back.

Sarah

A historic building with a courtyard, surrounded by lush greenery and trees.

Equo Suites

Castiglione del Lago

10/10 Excellent

Louise

A swimming pool with clear water, surrounded by lounge chairs and a pergola.

Morami Wine Agriturismo

Castiglione del Lago

10/10 Excellent

Cheryl

An arched entrance with a wooden balcony, a tiled floor, and a door leading inside.

Hotel Boutique Castiglione del Lago

Contrada Castello

10/10 Excellent

Jane

Agriturismo Parco Fiorito

Tuoro sul Trasimeno

10/10 Excellent

Anonymous traveller

A spacious dining area with a long wooden table, multiple chairs, and hanging wicker lamps.

Agriturismo Antica Corte

Montepulciano

10/10 Excellent

Farah

An aerial view of a vineyard estate with rows of grapevines, a swimming pool, and a red building.

Podere La Rocca

Montepulciano

10/10 Excellent

Giovanni

A gazebo with a glass enclosure, surrounded by potted plants and wicker furniture, overlooking a scenic landscape.

Il Falconiere - Relais e Chateaux

Cortona

10/10 Excellent

Malcolm

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, apart-hotels, 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 favorite 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 depends 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 £55 per night. Entering your travel dates in the search wizard you might find 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?

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome: This holiday home rental outside of Ossaia is located in a rural location, and has an outdoor pool, a fireplace 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 patio, a garden and a selection of games 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 Naturalistic Oasis La Valle, 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.

Search Holiday Rentals in Ossaia

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Ossaia holiday rentals

1. Casale dell'Assiolo

2. B&B Piccolo Hotel

3. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

4. iConic Wellness Resort

5. Vacation home with a panoramic terrace, ideal for families and couples

6. CASA AMBRA

7. Artisti del Cavallo Tourism

8. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

9. Montecchio di Cortona

10. San Michele al Borgo

11. Vicolo Della Scala Rooms - La Luna

12. Abbadia Sicille Relais

13. Cortona Shabby Chic House<br>(Independent & Balcony)

14. DormiVeglia B&B

15. Cortonas Rooftop Nest

16. Dolce Casa 2 by Tiny Away

17. Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

18. Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

19. Fontelunga Hotel & Villas

20. Dolce Casa 1 by Tiny Away

Find holiday rentals that suit your style

Top Ossaia Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

Find out more about Ossaia

Ossaia holiday rentals: An excellent choice for every season

How to find incredible deals on Ossaia rentals

Frequently Asked Questions

Are there holiday rentals in Ossaia?

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

How many holiday rentals are there in Ossaia?

What’s there to see and do in Ossaia?

What’s a holiday rental in Ossaia like?