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Ossaia Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Ossaia vacation rentals

An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is ￥22,459
￥25,060 total
includes taxes & fees
Nov 2 - Nov 3
B&B Piccolo Hotel
A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

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)
"Beautiful location. Can't wait to go back."
United States
Dawn H.
The price is ￥16,579
￥17,288 total
includes taxes & fees
Oct 12 - Oct 13
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

3. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is ￥33,005
￥36,572 total
includes taxes & fees
Nov 11 - Nov 12
CASA AMBRA
A park with picnic tables, a playground, and a gravel path.

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

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is ￥12,412
￥15,604 total
includes taxes & fees
Oct 14 - Oct 15
Holiday home with panoramic terrace ideal for families and couples
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

5. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is ￥15,193
￥17,422 total
includes taxes & fees
Oct 13 - Oct 14
Vicolo Della Scala Rooms - La Luna
Dining

6. 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 ￥14,008
￥17,200 total
includes taxes & fees
Oct 19 - Oct 20
Montecchio di Cortona
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

7. 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 ￥20,243
￥22,976 total
includes taxes & fees
Oct 15 - Oct 16
San Michele al Borgo
A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

8. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is ￥7,979
￥11,880 total
includes taxes & fees
Oct 12 - Oct 13
Happy Nest Tuscany Between Florence and Rome
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

9. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
The price is ￥12,864
￥14,859 total
includes taxes & fees
Oct 22 - Oct 23
Artisti del Cavallo Tourism
Pool

10. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (41 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is ￥13,348
￥15,747 total
includes taxes & fees
Oct 25 - Oct 26
iConic Wellness Resort
A staircase with two lit lanterns on the wall.

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 ￥21,899
￥25,623 total
includes taxes & fees
Oct 18 - Oct 19
Cortona Shabby Chic House<br>(Independent & Balcony)
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

12. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay!"
Canada
Brian
The price is ￥38,439
￥42,992 total
includes taxes & fees
Oct 12 - Oct 13
Fontelunga Hotel & Villas
A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

13. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is ￥12,022
￥17,342 total
includes taxes & fees
Oct 12 - Oct 13
Dolce Casa 2 by Tiny Away
A spa area with a stone-walled arch, a hot tub, and a small window.

14. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (30 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is ￥15,887
￥18,185 total
includes taxes & fees
Nov 9 - Nov 10
DormiVeglia B&B
A building with a stone facade, multiple windows, and a balcony.

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

Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
Cortona
10.0 out of 10, Exceptional, (1 review)
"Pros: il luogo che ci circondava rilassante ottimo. Cons: nulla come dicevo luogo ottimo."
Italy
Anonymous traveler
The price is ￥40,870
￥48,245 total
includes taxes & fees
Oct 12 - Oct 13
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
A stone building with a balcony, an archway, and potted plants.

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

Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Cortona
8.8 out of 10, Excellent, (3 reviews)
"Angelo was so friendly. He met us at the property and showed us around. The house is beautiful and peaceful. Thank you for a lovely stay."
United States
Bonnie B.
The price is ￥22,706
￥23,415 total
includes taxes & fees
Nov 2 - Nov 3
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Exterior detail

17. Abode of the Sun

Abode of the Sun
Passignano sul Trasimeno
10.0 out of 10, Exceptional, (1 review)
"We had a great stay in Passignano. The apartments location was perfect to explore town"
United States
Ted M.
The price is ￥19,150
￥22,342 total
includes taxes & fees
Oct 14 - Oct 15
Abode of the Sun
A nighttime view of a building with a staircase leading to a door, surrounded by greenery and a well-lit pathway.

18. Borgo Dolciano

Borgo Dolciano
Chiusi
9.0 out of 10, Wonderful, (26 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 ￥23,485
￥26,189 total
includes taxes & fees
Oct 13 - Oct 14
Borgo Dolciano
Room

19. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is ￥12,935
￥18,255 total
includes taxes & fees
Oct 12 - Oct 13
Dolce Casa 1 by Tiny Away
A stone building with a balcony and a small garden area with plants.

20. L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
The price is ￥9,100
￥10,010 total
includes taxes & fees
Oct 20 - Oct 21
L'Antica Sosta
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

10/10 Excellent
"Beautiful hotel up high in this hill town. Great service and restaurants."
Tarrant 1-night trip
Posted 13 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
  • 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.