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Ossaia Vacation Rentals

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Check prices for these dates

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

Our top choices for Ossaia vacation 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 P8,625
P9,767 total
includes taxes & fees
Oct 14 - Oct 15
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 P14,322
P15,859 total
includes taxes & fees
Nov 11 - Nov 12
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)
"Good house for one night. "
Germany
Heiner
The price is P5,080
P5,868 total
includes taxes & fees
Oct 22 - Oct 23
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)
The price is P8,784
P9,943 total
includes taxes & fees
Oct 14 - Oct 15
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 P6,250
P7,155 total
includes taxes & fees
Oct 15 - Oct 16
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 P5,271
P6,218 total
includes taxes & fees
Nov 5 - Nov 6
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 P17,650
P19,695 total
includes taxes & fees
Oct 14 - Oct 15
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)
"Great Historical location."
Canada
Robert
The price is P5,296
P6,037 total
includes taxes & fees
Oct 15 - Oct 16
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 P6,894
P7,863 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, (71 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is P6,789
P9,211 total
includes taxes & fees
Nov 9 - Nov 10
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 P9,319
P10,392 total
includes taxes & fees
Oct 14 - Oct 15
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 P4,084
P4,492 total
includes taxes & fees
Oct 15 - Oct 16
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

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
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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.