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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Ossaia holiday rentals

View from room
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 Rp1.225.667
Rp1.407.408 total
includes taxes & fees
6 Jan - 7 Jan 2026
Abbadia Sicille Relais
Exterior
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
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
Premium bedding, down duvets, minibar, in-room safe
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 Rp3.046.427
Rp3.429.916 total
includes taxes & fees
18 Jan - 19 Jan 2026
La Locanda di San Francesco
Lobby
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 Rp1.470.575
Rp1.696.478 total
includes taxes & fees
13 Jan - 14 Jan 2026
Residenza Fabroni
Balcony
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 Rp1.523.115
Rp1.793.755 total
includes taxes & fees
18 Jan - 19 Jan 2026
Cameracaffè Centro
Deluxe Double Room | View from room
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
Daily buffet breakfast (EUR 10 per person)
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
Free daily cooked-to-order breakfast
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 Rp2.060.758
Rp2.345.679 total
includes taxes & fees
8 Jan - 9 Jan 2026
San Michele al Borgo
Outdoor pool, pool loungers
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 Rp2.447.150
Rp2.731.288 total
includes taxes & fees
3 Jan - 4 Jan 2026
Borgo Dolciano
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
Bed & Breakfast Vicolo dell'Oste
Interior
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 Rp3.021.358
Rp3.402.339 total
includes taxes & fees
29 Dec - 30 Dec
Delcorto Suites
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 Rp4.451.236
Rp4.975.205 total
includes taxes & fees
30 Dec - 31 Dec
Il Tosco
Luxury Room, Jetted Tub, City View | Free WiFi, bed sheets
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 Rp1.354.724
Rp1.608.466 total
includes taxes & fees
8 Jan - 9 Jan 2026
B&B 52cento
Interior entrance
Poggio del Sole

Holiday Home in Castiglione del Lago

Poggio del Sole
8.0 out of 10, Very good, (4)
"El hotel no alcanzó el agua caliente y no se pudo bañar parte de la familia no contaba con suficientes amenidades "
Mexico
RAUL
Poggio del Sole
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 Rp1.170.869
Rp1.287.956 total
includes taxes & fees
8 Jan - 9 Jan 2026
L'Antica Sosta
Property grounds
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 Rp1.371.255
Rp1.547.804 total
includes taxes & fees
5 Jan - 6 Jan 2026
Artisti del Cavallo Tourism
Business centre
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
Exterior
Castello di Gargonza

Residence in Monte San Savino

Castello di Gargonza
3.0 star property
9.2 out of 10, Wonderful, (39)
"All of the hotel staff did an outstanding job. Our room had everything we needed and the restaurant was great. Breakfast was exceptional. Special shoutout to Neri, the owner, for taking such good care of us. "
United States
Diane
Castello di Gargonza
Front of property
Locanda Antico Borgo

Townhouse in Civitella in Val di Chiana

Locanda Antico Borgo
9.2 out of 10, Wonderful, (20)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
The price is Rp1.971.160
Rp2.168.275 total
includes taxes & fees
29 Dec - 30 Dec
Locanda Antico Borgo
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 10 days ago
Monastero di Cortona Hotel & Spa

Find out more about Ossaia

Search for holiday rentals in Ossaia on Expedia.co.id! 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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  • 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 holiday rentals in Ossaia?

Yes, there are holiday rentals close to the most popular sights in Ossaia, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Ossaia?

With 7 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Giuseppe Garibaldi Memorial and Villa Bramasole.

What’s a holiday rental in Ossaia like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ossaia. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for family trips.