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Ossaia Vacation Rentals

Check prices for these dates

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

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
$147 nightly
The price is $166
Aug 18 - Aug 19
Total with taxes and fees
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.
$108 nightly
The price is $113
Aug 17 - Aug 18
Total with taxes and fees
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Apartment (1 Bedroom) | Front of property

3. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
$98 nightly
The price is $113
Aug 25 - Aug 26
Total with taxes and fees
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 traveler
$652 nightly
The price is $657
Sep 16 - Sep 17
Total with taxes and fees
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
$94 nightly
The price is $94
Aug 19 - Aug 20
Total with taxes and fees
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.
$244 nightly
The price is $249
Sep 2 - Sep 3
Total with taxes and fees
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 traveler
$675 nightly
The price is $681
Aug 30 - Aug 31
Total with taxes and fees
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.
$190 nightly
The price is $193
Aug 17 - Aug 18
Total with taxes and fees
Cortonas Rooftop Nest
Junior Suite | Terrace/patio

9. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
$107 nightly
The price is $123
Sep 13 - Sep 14
Total with taxes and fees
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
$125 nightly
The price is $142
Aug 23 - Aug 24
Total with taxes and fees
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
$164 nightly
The price is $167
Aug 28 - Aug 29
Total with taxes and fees
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
$232 nightly
The price is $260
Aug 18 - Aug 19
Total with taxes and fees
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
$190 nightly
The price is $213
Aug 23 - Aug 24
Total with taxes and fees
Abbadia Sicille Relais
Apartment (1 Bedroom) | Front of property

14. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
$100 nightly
The price is $115
Aug 18 - Aug 19
Total with taxes and fees
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.
$112 nightly
The price is $112
Aug 24 - Aug 25
Total with taxes and fees
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.
$160 nightly
The price is $162
Aug 17 - Aug 18
Total with taxes and fees
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
$242 nightly
The price is $271
Sep 14 - Sep 15
Total with taxes and fees
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
$162 nightly
The price is $182
Aug 23 - Aug 24
Total with taxes and fees
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.
$355 nightly
The price is $355
Sep 1 - Sep 2
Total with taxes and fees
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
$123 nightly
The price is $138
Aug 17 - Aug 18
Total with taxes and fees
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

Everything you need to know about Ossaia vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ossaia vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ossaia vacation 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 low season months. For more hustle and bustle, you may prefer to visit Ossaia in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ossaia rentals

At Expedia, we put the best Ossaia vacation 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 vacation.

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 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.