Ossaia Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Ossaia

View from room
Abbadia Sicille Relais

Abbadia Sicille Relais

4.0 star property
Trequanda
8.8 out of 10, Excellent, (163)
"We stayed there for 1 night our our way to Rome. BEAUTIFUL. Bed was very comfortable as well. 10/10 will recommend to everyone "
United States
Brittnay
The price is P4,693
P5,367 total
includes taxes & fees
Dec 15 - Dec 16
Abbadia Sicille Relais
Bar (on property)
La Piccola Locanda

La Piccola Locanda

Chiusi
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
Free WiFi, bed sheets
Bellarmino Boutique Apartments

Bellarmino Boutique Apartments

Montepulciano
The price is P4,211
P4,905 total
includes taxes & fees
Dec 15 - Dec 16
Bellarmino Boutique Apartments
Premium bedding, down comforters, minibar, in-room safe
La Locanda di San Francesco

La Locanda di San Francesco

Montepulciano
9.8 out of 10, Exceptional, (127)
"Beautiful property nestled at the top of montepulciano. Very helpful owner Luca and unmatched hospitality! "
United States
Alizeh
The price is P9,002
P10,175 total
includes taxes & fees
Dec 5 - Dec 6
La Locanda di San Francesco
Exterior
Meublé Il Riccio

Meublé Il Riccio

Montepulciano
9.6 out of 10, Exceptional, (85)
"Beautiful hotel."
United States
Helen
Meublé Il Riccio
Balcony
Cameracaffè Centro

Cameracaffè Centro

Arezzo Centro Storico
8.6 out of 10, Excellent, (177)
"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 P4,554
P5,422 total
includes taxes & fees
Dec 1 - Dec 2
Cameracaffè Centro
Exterior
L'Antica Sosta

L'Antica Sosta

Corciano
9.4 out of 10, Exceptional, (3)
"Molto accoglienti e gentili "
Italy
Valentina
The price is P3,761
P4,137 total
includes taxes & fees
Dec 2 - Dec 3
L'Antica Sosta
View from room
Affitacamere Maria Gabriella

Affitacamere Maria Gabriella

Pienza
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
Daily buffet breakfast (EUR 10 per person)
DormiVeglia B&B

DormiVeglia B&B

Monte San Savino
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
Lobby
Residenza Fabroni

Residenza Fabroni

Montepulciano
8.8 out of 10, Excellent, (93)
"We had a great stay! Beautiful on the roof top terrace!"
United States
Jennifer
The price is P5,012
P5,788 total
includes taxes & fees
Nov 19 - Nov 20
Residenza Fabroni
Exterior
Casa di Cristina

Casa di Cristina

Casamaggiore
The price is P4,661
P5,127 total
includes taxes & fees
Nov 21 - Nov 22
Casa di Cristina
Property grounds
Artisti del Cavallo Tourism

Artisti del Cavallo Tourism

Foiano della Chiana
8.4 out of 10, Very Good, (24)
"Good house for one night. "
Germany
Heiner
The price is P4,801
P5,418 total
includes taxes & fees
Nov 19 - Nov 20
Artisti del Cavallo Tourism
Free daily cooked-to-order breakfast
San Michele al Borgo

San Michele al Borgo

Castiglion Fiorentino
9.8 out of 10, Exceptional, (9)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is P7,487
P8,373 total
includes taxes & fees
Nov 23 - Nov 24
San Michele al Borgo
Seasonal outdoor pool, pool umbrellas, sun loungers
Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside

Trequanda
Luxury resort in the Tuscan countryside
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ossaia Hotel Reviews

A Point Arezzo Park Hotel

A Point Arezzo Park Hotel

6/10 Okay
"The room was in quite poor condition. There was only lukewarm water, the heating was noisy, the tv didn’t work, the lights over the bed flashed and the toilet seat was loose. It was a very stylish hotel but it just needs some maintenance. The breakfast was very good and the bed was comfortable "
Zena 1-night trip
Posted 3 days ago
A Point Arezzo Park Hotel

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 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 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.