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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Ossaia holiday rentals

Lunch and dinner served, local cuisine

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
The price is ₹23,284
₹26,057 total
includes taxes & fees
11 May - 12 May
Castello di Gargonza
Bar (on property)

La Piccola Locanda

La Piccola Locanda
Chiusi
7.8 out of 10, Good, (11 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
The price is ₹11,269
₹12,617 total
includes taxes & fees
13 May - 14 May
La Piccola Locanda
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (173 reviews)
"The room was really clean and as described. Unfortunately, the hotel restaurant was closed and that was not mentioned on the site. I learned about it the day before my arrival. Fortunately, the host had good restaurant suggestions. The hotel advertise a pool and a jacuzzi, they have both but the pool was VERY cold (normal in April) and the jacuzzi was not inviting (bee nest, Luke warm, in the shade...). Concerning the breakfast, note that it is not a buffet, a box get delivered to your room. You...
Canada
Chantal
The price is ₹16,887
₹18,909 total
includes taxes & fees
3 Jun - 4 Jun
Abbadia Sicille Relais
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (94 reviews)
"An amazingly beautiful and historic property. Our room had an incredible view. The staff was fantastic- welcoming and helpful. The location is spectacular. I highly recommend. "
United States
Hallie
The price is ₹15,432
₹17,417 total
includes taxes & fees
15 May - 16 May
Meublé Il Riccio
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (130 reviews)
"Loved this place ! Clean, modern, large rooms, perfect location and the owner kind and beyond attentive."
United States
Melissa
The price is ₹12,477
₹14,166 total
includes taxes & fees
1 Jun - 2 Jun
Bed & Breakfast Vicolo dell'Oste
BBQ/picnic Area

Residenza d'epoca Ca' de Principi

Residenza d'epoca Ca' de Principi
Piegaro
9.8 out of 10, Exceptional, (13 reviews)
"The hotel was charming, and the staff really nice. Breakfast had lots of options. The room was large and beautiful view of the hills. The bed was comfortable."
United States
Robyn
The price is ₹13,059
₹14,366 total
includes taxes & fees
22 May - 23 May
Residenza d'epoca Ca' de Principi
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (100 reviews)
"Beautiful apartment, well located, best host and yummy breakfast in a beautiful cafeteria close by. "
United States
Johanna
The price is ₹8,013
₹9,259 total
includes taxes & fees
12 May - 13 May
Residenza Fabroni
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (137 reviews)
"Beautiful quaint place to stay in Montepulciano. Stairs are doable to carry up luggage and the views of the valley are spectacular. Great location, can’t wait to stay again!"
Canada
Melissa
The price is ₹19,081
₹21,434 total
includes taxes & fees
10 May - 11 May
La Locanda di San Francesco
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (36 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is ₹9,370
₹10,974 total
includes taxes & fees
19 May - 20 May
iConic Wellness Resort
Exterior

San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is ₹12,832
₹14,560 total
includes taxes & fees
11 May - 12 May
San Michele al Borgo
Exterior

Borgo Dolciano

Borgo Dolciano
Chiusi
9.0 out of 10, Wonderful, (25 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 ₹14,443
₹16,108 total
includes taxes & fees
14 May - 15 May
Borgo Dolciano
Courtyard

Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (5 reviews)
"Amazing stay at this hotel I would recommend it. Great hospitality, clean and picture postcard views. "
United Kingdom
Liam
The price is ₹27,080
₹30,010 total
includes taxes & fees
12 May - 13 May
Fontelunga Hotel & Villas
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (35 reviews)
"Wonderful "
United States
Rocio Q
The price is ₹18,820
₹21,144 total
includes taxes & fees
17 May - 18 May
Delcorto Suites
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
"After a rather "bumpy" start the great hotel manager Flavia and her young & local, a yet commited staff (Mateo, Mathilde, each of them) made my stay at Monastero a place to remember and plan to come back with my family. The building is fantastic, very well referbished with soft shades of white that it's a joy to experience the "dolce fare niente" by the pool, wondering around the laberinth and discovering great views of the countryside and the redish roofs of Cortona from different points of views. The indoor pool though small it's a plus to unwind on a misty day. 5 days at Monastero felt short! Grazie mille Flavia and staff. Local Amaretto and biscotti will make their way to Punta del Este, Uruguay and enjoyed with so fond memorias."
ELSA MATILDE 4-night trip
Posted 1 day ago
Monastero di Cortona Hotel & Spa

Find out more about Ossaia

Holiday Rentals in Ossaia

Search for holiday rentals in Ossaia on Expedia.co.uk! 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 6 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 Villa Bramasole and Piazza della Repubblica.

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.