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Ossaia Vacation Rentals

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Check prices for these dates

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

Our top choices for Ossaia vacation 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 NT$4,498
NT$5,094 total
includes taxes & fees
Oct 25 - Oct 26
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 NT$7,470
NT$8,271 total
includes taxes & fees
Nov 5 - Nov 6
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 NT$4,581
NT$5,186 total
includes taxes & fees
Oct 29 - Oct 30
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 NT$2,420
NT$2,882 total
includes taxes & fees
Nov 16 - Nov 17
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 NT$2,649
NT$3,060 total
includes taxes & fees
Oct 27 - Oct 28
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 NT$9,205
NT$10,272 total
includes taxes & fees
Oct 26 - Oct 27
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 NT$3,879
NT$4,340 total
includes taxes & fees
Oct 25 - Oct 26
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 NT$2,420
NT$2,772 total
includes taxes & fees
Nov 22 - Nov 23
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 NT$3,595
NT$4,101 total
includes taxes & fees
Nov 8 - Nov 9
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 NT$3,541
NT$4,804 total
includes taxes & fees
Oct 28 - Oct 29
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 NT$4,837
NT$5,393 total
includes taxes & fees
Oct 26 - Oct 27
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 2 days ago
Nuovo Etruria Resort

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.

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.