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Ossaia Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Ossaia holiday rentals

A bedroom with a bed, a nightstand, a wall-mounted lamp, and a door with a calendar.

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.4 out of 10, Exceptional, (26 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is S$200
includes taxes & fees
25 Oct - 26 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 S$318
includes taxes & fees
6 Nov - 7 Nov
CASA AMBRA
A breakfast setting with a fireplace, a table with plates, glasses, and a croissant.

3. 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$192
includes taxes & fees
25 Oct - 26 Oct
San Michele al Borgo
Pool

4. 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 S$113
includes taxes & fees
16 Nov - 17 Nov
iConic Wellness Resort
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

5. 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 S$113
includes taxes & fees
1 Nov - 2 Nov
Artisti del Cavallo Tourism
An aerial view of a rectangular swimming pool with multiple white umbrellas and lounge chairs around it.

6. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay!"
Canada
Brian
The price is S$460
includes taxes & fees
15 Nov - 16 Nov
Fontelunga Hotel & Villas
A dining area with a wooden table, chairs, and a potted plant.

7. La Piccola Locanda

La Piccola Locanda
Chiusi
8.0 out of 10, Very good, (14 reviews)
"Very homey and wonderful people! We loved the restaurant below."
United States
autumn
The price is S$159
includes taxes & fees
21 Nov - 22 Nov
La Piccola Locanda
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, (185 reviews)
"Great Historical location."
Canada
Robert
The price is S$103
includes taxes & fees
23 Nov - 24 Nov
Abbadia Sicille Relais
An outdoor dining setup with a pool and lounge chairs in the background.

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 S$156
includes taxes & fees
23 Nov - 24 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, (74 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is S$176
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 S$212
includes taxes & fees
26 Oct - 27 Oct
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

Nuovo Etruria Resort

Nuovo Etruria Resort

8/10 Good
"When we arrived the gate to the hotel was locked. Called the hotel and then a person drove up and helped us to check in. He was very nice. The hotel is very old, but a decent place to stay for a night."
John 1-night trip
Posted 1 day ago
Nuovo Etruria Resort

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.