Ossaia Vacation Rentals

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Check prices for these dates

Tonight
Dec 22 - Dec 23
Tomorrow
Dec 23 - Dec 24
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Ossaia vacation rentals

Property entrance
Residenza Fabroni

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is ₩129,072
₩148,899 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Residenza Fabroni
Terrace/patio
Abbadia Sicille Relais

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ₩118,891
₩135,967 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Abbadia Sicille Relais
Panoramic Cottage, 1 Bedroom | Exterior
Affitacamere Maria Gabriella

Townhouse in Pienza

Affitacamere Maria Gabriella
9.8 out of 10, Exceptional, (51)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella
Interior
Meublé Il Riccio

Townhouse in Montepulciano

Meublé Il Riccio
9.8 out of 10, Exceptional, (86)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
Meublé Il Riccio
Porch
Cameracaffè Centro

Townhouse in Arezzo Centro Storico

Cameracaffè Centro
8.6 out of 10, Excellent, (179)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
The price is ₩143,125
₩167,817 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Cameracaffè Centro
Food court
La Locanda di San Francesco

Townhouse in Montepulciano

La Locanda di San Francesco
9.8 out of 10, Exceptional, (131)
"Great room-great staff-great location"
United States
Richard
The price is ₩264,235
₩297,579 total
includes taxes & fees
Jan 18 - Jan 19, 2026
La Locanda di San Francesco
Exterior
Bed & Breakfast Vicolo dell'Oste

Townhouse in Montepulciano

Bed & Breakfast Vicolo dell'Oste
9.6 out of 10, Exceptional, (128)
"Great hosts, central location "
United States
Alexander
The price is ₩183,960
₩209,271 total
includes taxes & fees
Dec 23 - Dec 24
Bed & Breakfast Vicolo dell'Oste
Exterior
Borgo Dolciano

Aparthotel in Chiusi

Borgo Dolciano
9.0 out of 10, Wonderful, (25)
"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 ₩249,149
₩277,522 total
includes taxes & fees
Dec 28 - Dec 29
Borgo Dolciano
Luxury Double or Twin Room, 1 Bedroom, Jetted Tub, City View | View from room
B&B 52cento

Townhouse in Arezzo Centro Storico

B&B 52cento
8.0 out of 10, Very Good, (73)
"Exactly how it is described and very near the train station. Walkable distance to all the things to do around there. I really enjoyed my stay there. "
United States
Maria de Lourdes
The price is ₩118,904
₩141,174 total
includes taxes & fees
Jan 8 - Jan 9, 2026
B&B 52cento
Exterior
San Michele al Borgo

Townhouse in Castiglion Fiorentino

San Michele al Borgo
9.8 out of 10, Exceptional, (9)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is ₩190,309
₩216,260 total
includes taxes & fees
Jan 7 - Jan 8, 2026
San Michele al Borgo
Exterior
L'Antica Sosta

Townhouse in Corciano

L'Antica Sosta
9.4 out of 10, Exceptional, (3)
"Molto accoglienti e gentili "
Italy
Valentina
The price is ₩102,767
₩113,044 total
includes taxes & fees
Jan 8 - Jan 9, 2026
L'Antica Sosta
Bar (on property)
La Piccola Locanda

Townhouse in Chiusi

La Piccola Locanda
8.8 out of 10, Excellent, (8)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
La Piccola Locanda
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub
DormiVeglia B&B

Townhouse in Monte San Savino

DormiVeglia B&B
10.0 out of 10, Exceptional, (27)
"This was our favourite B&B. The owner Simona was absolutely wonderful. The hot tub in our room was out of this world. If you have the chance to visite this gem…DO IT!!"
Canada
Claude
DormiVeglia B&B
Property entrance
Il Tosco

Residence in Montepulciano

Il Tosco
10.0 out of 10, Exceptional, (115)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is ₩390,684
₩436,672 total
includes taxes & fees
Dec 23 - Dec 24
Il Tosco
Suite Aria | Terrace/patio
Delcorto Suites

Residence in Montepulciano

Delcorto Suites
10.0 out of 10, Exceptional, (33)
"Exceptional service great building felt like a Medici!"
United States
gaetano
The price is ₩294,641
₩331,025 total
includes taxes & fees
Dec 29 - Dec 30
Delcorto Suites
Exterior
Artisti del Cavallo Tourism

Villa in Foiano della Chiana

Artisti del Cavallo Tourism
8.4 out of 10, Very Good, (24)
"Good house for one night. "
Germany
Heiner
The price is ₩125,509
₩141,520 total
includes taxes & fees
Dec 23 - Dec 24
Artisti del Cavallo Tourism
Reception
Allegra Toscana - Affittacamere Guest house

Townhouse in Arezzo Centro Storico

Allegra Toscana - Affittacamere Guest house
7.0 out of 10, Good, (16)
"Great location in Arezzo, easy and simple to find and access. Everything was exactly as we needed although we did not need to stay long."
United Kingdom
Justin
Allegra Toscana - Affittacamere Guest house
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Everything was perfect! Would like to give this Property a 6 Star rating. The staff made you feel like royalty!!"
Sabrina 4-night trip
Posted 3 days ago
Monastero di Cortona Hotel & Spa

Find out more about Ossaia

Search for Vacation rentals in Ossaia on Expedia.co.uk! You can easily find your home rentals, villas, Vacation 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 8 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 Giuseppe Garibaldi Memorial and Villa Bramasole.

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.