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Ossaia Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Ossaia vacation 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 ￥25,390
￥28,664 total
includes taxes & fees
Aug 16 - Aug 17
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 ￥17,051
￥17,780 total
includes taxes & fees
Aug 22 - Aug 23
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Outdoor dining

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

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is ￥11,582
￥14,891 total
includes taxes & fees
Sep 10 - Sep 11
Holiday home with panoramic terrace ideal for families and couples
Interior

4. 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 ￥26,658
￥39,159 total
includes taxes & fees
Sep 2 - Sep 3
La Finestra sul Teatro
Apartment (1 Bedroom) | Front of property

5. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is ￥15,788
￥18,096 total
includes taxes & fees
Aug 22 - Aug 23
Vicolo Della Scala Rooms - La Luna
Pool

6. 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 traveler
The price is ￥44,843
￥112,841 total
includes taxes & fees
Sep 6 - Sep 7
Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi
Interior

7. 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 ￥23,707
￥27,536 total
includes taxes & fees
Aug 28 - Aug 29
Cortona Shabby Chic House<br>(Independent & balcony)
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 ￥26,096
￥30,473 total
includes taxes & fees
Aug 17 - Aug 18
Cortonas Rooftop Nest
Junior Suite | Terrace/patio

9. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is ￥18,006
￥20,541 total
includes taxes & fees
Sep 7 - Sep 8
Casale dell'Assiolo
Dining

10. 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 ￥14,406
￥17,688 total
includes taxes & fees
Aug 24 - Aug 25
Montecchio di Cortona
Exterior

11. 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 ￥22,420
￥25,391 total
includes taxes & fees
Aug 22 - Aug 23
San Michele al Borgo
Exterior

12. Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy

Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy
Cortona
10.0 out of 10, Exceptional, (29 reviews)
"Great location with gorgeous views over the Chiana hills, and nearby restaurants. We enjoyed discovering Cortona and several hill towns in the ares"
United States
Patricia H.
Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy
Courtyard

13. 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 ￥38,084
￥42,622 total
includes taxes & fees
Aug 12 - Aug 13
Fontelunga Hotel & Villas
Terrace/patio

14. 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 ￥29,990
￥33,536 total
includes taxes & fees
Aug 23 - Aug 24
Abbadia Sicille Relais
Interior

15. 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 ￥18,236
￥25,531 total
includes taxes & fees
Aug 24 - Aug 25
The window on the tower apartment new castiglion fiorentino
Suite Aria | Terrace/patio

16. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (40 reviews)
"Time transported to the Renaissance at this beautiful, well-kept palazzo… Riccardo’s family did a truly amazing job restoring this place and the facilities are modern & without any discomfort."
American Samoa
Melissa Hyun Joo
The price is ￥28,023
￥31,560 total
includes taxes & fees
Aug 12 - Aug 13
Delcorto Suites
Food court

17. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (146 reviews)
"Lucca was the perfect host, very accommodating to any queries we had and was always willing to help during our stay Couldn’t recommend staying here highly enough - we had a great time staying here and would highly recommend if you are in the area definitely book here"
United Kingdom
Jonathan
The price is ￥21,180
￥24,033 total
includes taxes & fees
Aug 25 - Aug 26
La Locanda di San Francesco
Property entrance

18. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (104 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is ￥14,420
￥16,591 total
includes taxes & fees
Aug 21 - Aug 22
Residenza Fabroni
Interior

19. 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 ￥25,726
￥29,028 total
includes taxes & fees
Aug 15 - Aug 16
Meublé Il Riccio
Exterior

20. Borgo Dolciano

Borgo Dolciano
Chiusi
9.0 out of 10, Wonderful, (25 reviews)
"Lovely restored Tuscan villa and farmhouse. Very comfortable stay. Felt that the people who run it do so with a lot of heart and style. Great value too. "
Canada
Carla
The price is ￥28,758
￥32,002 total
includes taxes & fees
Aug 13 - Aug 14
Borgo Dolciano
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

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent
"Silverio and Beatrice and the whole staff are amazing and wonderful and helpful, the grounds, the room beautiful perfect,the food amazing the property just outstanding in every way truly picturesque and the bed very comfortable Grazie Grazie siete stupiendi!"
Anthony 5-night trip
Posted 5 hours ago
Relais Villa Grazianella - UNA Esperienze

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
  • Use the map to find apartments and other holiday homes in the Ossaia neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Ossaia while they last

Look no further and take a look at our great range of rental properties in Ossaia!

Frequently asked questions

Are there vacation rentals in Ossaia?

Yes, you can find vacation rentals near top local attractions in Ossaia, or you can select a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Ossaia?

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome: This vacation home rental near Ossaia is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Ossaia?

With 7 Expedia vacation rentals, you're sure 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 larger area, you’ll find Villa Bramasole and Piazza della Repubblica.

What’s a vacation rental in Ossaia like?

Vacation rentals are private properties where you can stay for a couple of days or more in Ossaia. Vacation rentals offer amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.