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Ossaia Vacation Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Ossaia holiday 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 RM564
RM638 total
includes taxes & fees
14 Oct - 15 Oct
B&B Piccolo Hotel
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

2. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is RM932
RM1,032 total
includes taxes & fees
5 Nov - 6 Nov
CASA AMBRA
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

3. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
The price is RM331
RM382 total
includes taxes & fees
22 Oct - 23 Oct
Artisti del Cavallo Tourism
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

4. 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 RM572
RM647 total
includes taxes & fees
14 Oct - 15 Oct
San Michele al Borgo
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 RM407
RM466 total
includes taxes & fees
15 Oct - 16 Oct
Vicolo Della Scala Rooms - La Luna
Pool

6. 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 RM343
RM405 total
includes taxes & fees
25 Oct - 26 Oct
iConic Wellness Resort
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

7. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay!"
Canada
Brian
The price is RM1,149
RM1,282 total
includes taxes & fees
14 Oct - 15 Oct
Fontelunga Hotel & Villas
A historic building with a tower, a courtyard, and a well-lit entrance.

8. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (184 reviews)
The price is RM343
RM391 total
includes taxes & fees
15 Oct - 16 Oct
Abbadia Sicille Relais
A spa area with a stone-walled arch, a hot tub, and a small window.

9. 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 RM449
RM512 total
includes taxes & fees
8 Nov - 9 Nov
DormiVeglia B&B
A patio area with outdoor seating, potted plants, and a view of the landscape.

10. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (71 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is RM442
RM599 total
includes taxes & fees
28 Oct - 29 Oct
Affitacamere Maria Gabriella
A nighttime view of a building with a staircase leading to a door, surrounded by greenery and a well-lit pathway.

11. 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 RM604
RM673 total
includes taxes & fees
14 Oct - 15 Oct
Borgo Dolciano
A stone building with a balcony and a small garden area with plants.

12. L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
The price is RM266
RM292 total
includes taxes & fees
14 Oct - 15 Oct
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
"Frederico went above and beyond to transfer us to our villa and Giulio was a fantastic bartender"
lise 1-night trip
Posted 1 hour ago
Monastero di Cortona Hotel & Spa

Find out more about Ossaia

Search for holiday rentals in Ossaia on Expedia.co.uk! 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 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.

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.