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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 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 ฿9,244
฿10,319 total
includes taxes & fees
15 Apr - 16 Apr
Castello di Gargonza
Panoramic Cottage, 1 Bedroom | Exterior

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (53 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
The price is ฿3,654
฿4,958 total
includes taxes & fees
15 Apr - 16 Apr
Affitacamere Maria Gabriella
Bar (on property)

La Piccola Locanda

La Piccola Locanda
Chiusi
7.8 out of 10, Good, (10 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 ฿3,990
฿4,464 total
includes taxes & fees
15 Apr - 16 Apr
La Piccola Locanda
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (171 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ฿4,163
฿4,692 total
includes taxes & fees
19 Apr - 20 Apr
Abbadia Sicille Relais
Exterior

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
The price is ฿7,557
฿8,425 total
includes taxes & fees
20 Apr - 21 Apr
Luxury resort in the Tuscan countryside
Exterior

L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
The price is ฿2,069
฿2,276 total
includes taxes & fees
22 Apr - 23 Apr
L'Antica Sosta
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 ฿5,409
฿6,025 total
includes taxes & fees
23 Apr - 24 Apr
Borgo Dolciano
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 ฿3,357
฿3,843 total
includes taxes & fees
15 Apr - 16 Apr
Bed & Breakfast Vicolo dell'Oste
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (91 reviews)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
The price is ฿5,352
฿6,037 total
includes taxes & fees
15 Apr - 16 Apr
Meublé Il Riccio
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 ฿9,064
฿10,046 total
includes taxes & fees
16 Apr - 17 Apr
Fontelunga Hotel & Villas
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 ฿2,837
฿3,347 total
includes taxes & fees
4 May - 5 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 ฿3,585
฿4,094 total
includes taxes & fees
16 Apr - 17 Apr
San Michele al Borgo
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (98 reviews)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is ฿2,649
฿3,065 total
includes taxes & fees
19 Apr - 20 Apr
Residenza Fabroni
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

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

10/10 Excellent
"Absolutely an amazing stay. Very charming and well kept. Essentially a resort with a palatial feel. Loved walking the grounds and relaxing. Excellent restaurant, breakfast was included. The setting is quiet and beautiful. Will book again. "
Melissa 1-night trip
Posted 21 hours ago
Precise Tale Poggio Alla Sala

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:

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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 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 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.