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Ossaia Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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, (24 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is S$227
includes taxes & fees
23 Sept - 24 Sept
B&B Piccolo Hotel
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

2. 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 S$445
includes taxes & fees
19 Sept - 20 Sept
Fontelunga Hotel & Villas
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 S$203
includes taxes & fees
19 Sept - 20 Sept
CASA AMBRA

4. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is S$184
includes taxes & fees
6 Oct - 7 Oct
Casale dell'Assiolo
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

5. 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 S$197
includes taxes & fees
9 Sept - 10 Sept
San Michele al Borgo
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

6. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is S$145
includes taxes & fees
9 Oct - 10 Oct
Vicolo Della Scala Rooms - La Luna
A historic building with a tower, a courtyard, and a well-lit entrance.

7. 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 S$199
includes taxes & fees
6 Oct - 7 Oct
Abbadia Sicille Relais
A terrace with a table set for breakfast, overlooking a scenic landscape.

8. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (43 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is S$297
includes taxes & fees
9 Sept - 10 Sept
Delcorto Suites
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

Hotel Villa Paradiso

Hotel Villa Paradiso

10/10 Excellent
"Lovely outdoor pool with waiter service"
Stephen 7-night trip
Posted 5 hours ago
Hotel Villa Paradiso

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.