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Ossaia Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Ossaia vacation rentals

Lobby

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (23 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is P9,414
P10,643 total
includes taxes & fees
Sep 2 - Sep 3
B&B Piccolo Hotel
Room

2. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is P8,817
P9,914 total
includes taxes & fees
Sep 25 - Sep 26
CASA AMBRA
Terrace/patio

3. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is P7,431
P8,463 total
includes taxes & fees
Sep 7 - Sep 8
Casale dell'Assiolo
Front of property

4. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is P6,412
P7,341 total
includes taxes & fees
Sep 10 - Sep 11
Vicolo Della Scala Rooms - La Luna
Exterior

5. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very Good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is P5,212
P6,020 total
includes taxes & fees
Sep 10 - Sep 11
Artisti del Cavallo Tourism
Exterior

6. 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 P9,013
P10,201 total
includes taxes & fees
Sep 10 - Sep 11
San Michele al Borgo
Property entrance

7. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (104 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is P5,007
P5,795 total
includes taxes & fees
Aug 30 - Aug 31
Residenza Fabroni
Exterior

8. L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
The price is P4,204
P4,624 total
includes taxes & fees
Sep 7 - Sep 8
L'Antica Sosta
Exterior

9. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (139 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is P7,800
P8,868 total
includes taxes & fees
Sep 1 - Sep 2
Bed & Breakfast Vicolo dell'Oste
Pool

10. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (40 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is P7,294
P8,456 total
includes taxes & fees
Aug 31 - Sep 1
iConic Wellness Resort
Bar (on property)

11. La Piccola Locanda

La Piccola Locanda
Chiusi
8.0 out of 10, Very Good, (13 reviews)
"Very homey and wonderful people! We loved the restaurant below."
United States
autumn
The price is P7,657
P8,567 total
includes taxes & fees
Aug 29 - Aug 30
La Piccola Locanda
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

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Staff was helpful , and the room was clean. The Antica Casina di Caccia dining with wine pairing was absolutely amazing. Also took some great pictures in the garden. The breakfast was nice too."
Yan Bo 1-night trip
Posted 11 days ago
Villa di Piazzano - Small Luxury Hotel of the World

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:

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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.