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Check prices for these dates

Tonight
13 Jan - 14 Jan
Tomorrow
14 Jan - 15 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for Ossaia holiday rentals

Terrace/patio
Abbadia Sicille Relais

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is 1.755.335 ₫
2.022.814 ₫ total
includes taxes & fees
14 Jan - 15 Jan
Abbadia Sicille Relais
Bar (on property)
La Piccola Locanda

Townhouse in Chiusi

La Piccola Locanda
8.8 out of 10, Excellent, (8 reviews)
"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
Property entrance
Residenza Fabroni

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (95 reviews)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is 2.280.419 ₫
2.630.727 ₫ total
includes taxes & fees
23 Jan - 24 Jan
Residenza Fabroni
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 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
DormiVeglia B&B
Exterior
L'Antica Sosta

Townhouse in Corciano

L'Antica Sosta
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
The price is 1.815.664 ₫
1.997.230 ₫ total
includes taxes & fees
19 Jan - 20 Jan
L'Antica Sosta
Panoramic Cottage, 1 Bedroom | Exterior
Affitacamere Maria Gabriella

Townhouse in Pienza

Affitacamere Maria Gabriella
9.8 out of 10, Exceptional, (51 reviews)
"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
Exterior
Bed & Breakfast Vicolo dell'Oste

Townhouse in Montepulciano

Bed & Breakfast Vicolo dell'Oste
9.6 out of 10, Exceptional, (128 reviews)
"Great hosts, central location "
United States
Alexander
Bed & Breakfast Vicolo dell'Oste
Food court
La Locanda di San Francesco

Townhouse in Montepulciano

La Locanda di San Francesco
9.8 out of 10, Exceptional, (131 reviews)
"Great room-great staff-great location"
United States
Richard
The price is 4.223.712 ₫
4.768.350 ₫ total
includes taxes & fees
19 Jan - 20 Jan
La Locanda di San Francesco
Interior
Meublé Il Riccio

Townhouse in Montepulciano

Meublé Il Riccio
9.8 out of 10, Exceptional, (86 reviews)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
Meublé Il Riccio
Exterior
San Michele al Borgo

Townhouse in Castiglion Fiorentino

San Michele al Borgo
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is 3.001.098 ₫
3.423.474 ₫ total
includes taxes & fees
14 Jan - 15 Jan
San Michele al Borgo
Interior entrance
Poggio del Sole

Holiday Home in Castiglione del Lago

Poggio del Sole
8.0 out of 10, Very good, (4 reviews)
"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
Artisti del Cavallo Tourism

Villa in Foiano della Chiana

Artisti del Cavallo Tourism
8.4 out of 10, Very good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is 2.217.478 ₫
2.500.359 ₫ total
includes taxes & fees
15 Jan - 16 Jan
Artisti del Cavallo Tourism
Deluxe Apartment, 2 Bedrooms, Balcony | Free WiFi, bed sheets
Bellarmino Boutique Apartments

Apartment in Montepulciano

Bellarmino Boutique Apartments
6.0 out of 10, (1 review)
"Heat didnt work, it was FREEZING. Contact didnt seem to be local, seemed like they were managing remotely and couldnt or wouldnt send anyone to help. Nor did they really seem to care. Beautiful area though!"
United States
JON
The price is 2.113.810 ₫
2.447.786 ₫ total
includes taxes & fees
14 Jan - 15 Jan
Bellarmino Boutique Apartments
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 great! Lovely hotel "
Laura 2-night trip
Posted 9 days ago
Monastero di Cortona Hotel & Spa

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.