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Ossaia Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Ossaia holiday rentals

Lobby

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (23 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is HK$1,150
HK$1,301 total
includes taxes & fees
25 Aug - 26 Aug
B&B Piccolo Hotel
Property grounds

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

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
10.0 out of 10, Exceptional, (8 reviews)
"This place was such a great find! So central and easily reachable. We really enjoyed our stay!"
United States
Julie R.
The price is HK$849
HK$885 total
includes taxes & fees
17 Aug - 18 Aug
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Front of property

3. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is HK$906
HK$1,033 total
includes taxes & fees
18 Aug - 19 Aug
Vicolo Della Scala Rooms - Il Sole
Pool

4. Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi

Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi
Cortona (AR)
9.0 out of 10, Wonderful, (2 reviews)
"Pros: Die Anlage strahlt einen wunderbaren nostalgischen Charme aus. Elisa hat sich hervorragend um uns gekümmert. Per Whatsapp wurden sämtliche Fragen in Kürze geklärt. Cons: Die Terrasse ist kaum zu nützen, da vor allem am Abend die Mückenplage unangenehm ist. Die Fenster und Türen der Wohnung haben alle Fliegen- und Mückengitter."
Germany
Anonymous traveller
The price is HK$1,794
HK$5,152 total
includes taxes & fees
14 Sept - 15 Sept
Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi
Outdoor dining

5. Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is HK$572
HK$735 total
includes taxes & fees
19 Aug - 20 Aug
Holiday home with panoramic terrace ideal for families and couples
Interior

6. La Finestra sul Teatro

La Finestra sul Teatro
Cortona Old Town
9.8 out of 10, Exceptional, (38 reviews)
"This was perfectly clean. The host was perfect."
United States
Michelle H.
The price is HK$1,316
HK$1,952 total
includes taxes & fees
3 Sept - 4 Sept
La Finestra sul Teatro
Exterior

7. Holiday Home 'Frantoio 5 Superior' with Shared Pool, Wi-Fi and Air Conditioning

Holiday Home 'Frantoio 5 Superior' with Shared Pool, Wi-Fi and Air Conditioning
Cortona
10.0 out of 10, Exceptional, (2 reviews)
"Pros: The pool and the quality of the house Cons: Gym was not open due to renovation"
United States
Anonymous traveller
The price is HK$4,963
HK$5,340 total
includes taxes & fees
30 Aug - 31 Aug
Holiday Home 'Frantoio 5 Superior' with Shared Pool, Wi-Fi and Air Conditioning
Property grounds

8. Cortonas Rooftop Nest

Cortonas Rooftop Nest
Cortona Old Town
10.0 out of 10, Exceptional, (12 reviews)
"Absolute gem of a property. Margherita is an excellent host as well!"
United States
Robin F.
The price is HK$1,299
HK$1,517 total
includes taxes & fees
22 Aug - 23 Aug
Cortonas Rooftop Nest
Terrace/patio

9. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is HK$936
HK$1,066 total
includes taxes & fees
7 Sept - 8 Sept
Casale dell'Assiolo
Exterior

10. San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is HK$1,139
HK$1,289 total
includes taxes & fees
22 Aug - 23 Aug
San Michele al Borgo
Interior

11. Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Shabby Chic House<br>(Independent & balcony)
Cortona Old Town
10.0 out of 10, Exceptional, (3 reviews)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
The price is HK$1,121
HK$1,312 total
includes taxes & fees
28 Aug - 29 Aug
Cortona Shabby Chic House<br>(Independent & balcony)
Courtyard

12. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay here! The hosts and staff were super warm and friendly. Breakfast had a wide choice and we liked the evening drinks set up too! The hotel doggies were definitely a highlight ☺️ we’d love to come back!"
United Kingdom
Shelby
The price is HK$1,915
HK$2,143 total
includes taxes & fees
17 Aug - 18 Aug
Fontelunga Hotel & Villas
Terrace/patio

13. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (178 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is HK$1,493
HK$1,670 total
includes taxes & fees
23 Aug - 24 Aug
Abbadia Sicille Relais
Front of property

14. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is HK$810
HK$928 total
includes taxes & fees
18 Aug - 19 Aug
Vicolo Della Scala Rooms - La Luna
Dining

15. Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2 reviews)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is HK$717
HK$881 total
includes taxes & fees
24 Aug - 25 Aug
Montecchio di Cortona
Interior

16. The window on the tower apartment new castiglion fiorentino

The window on the tower apartment new castiglion fiorentino
Castiglion fiorentino
10.0 out of 10, Exceptional, (1 review)
"Large apartment 4 floors above the town. Easy walking to anywhere in the area. Great shower and large bathroom. Equipped kitchen with big refrigerator. Living room with TV and dining table and couch. Large bedroom with fan. Also, there is a hairdryer and ironing board and iron. You are very close to walk to restaurants and stores, About a mile from the train station up a hill but the hostess helped us with transport.Overall, an excellent stay for my wife and I. (Be aware the room is 4...
United States
aric w.
The price is HK$908
HK$1,271 total
includes taxes & fees
17 Aug - 18 Aug
The window on the tower apartment new castiglion fiorentino
Lunch and dinner served

17. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (44 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
The price is HK$1,960
HK$2,193 total
includes taxes & fees
17 Aug - 18 Aug
Castello di Gargonza
Interior

18. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (115 reviews)
"It was very well located ."
Canada
Marlenne
The price is HK$1,294
HK$1,459 total
includes taxes & fees
22 Aug - 23 Aug
Meublé Il Riccio
Property grounds

19. Gorgeously restored tranquil farmhouse

Gorgeously restored tranquil farmhouse
Castiglione Del Lago PG
9.6 out of 10, Exceptional, (5 reviews)
"Nice relaxed location, a generous sized cottage with all the amenities, and excellent feedback from the client if we had queries. A perfect stay"
United Kingdom
Nigel G.
The price is HK$2,444
HK$2,784 total
includes taxes & fees
1 Sept - 2 Sept
Gorgeously restored tranquil farmhouse
Bar (on property)

20. La Piccola Locanda

La Piccola Locanda
Chiusi
8.0 out of 10, Very good, (12 reviews)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
The price is HK$964
HK$1,079 total
includes taxes & fees
17 Aug - 18 Aug
La Piccola Locanda
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

8/10 Good
"Hotel was perfect. Price was a bit high and very difficult parking"
Daniel 2-night trip
Posted 12 hours ago
Monastero di Cortona Hotel & Spa

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:

  • View our selection of featured holiday rentals in Ossaia
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Look no further and take a look at our great range of rental properties in Ossaia!

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.