Ossaia Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Ossaia vacation rentals

Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (102 reviews)
"Beautiful apartment, well located, best host and yummy breakfast in a beautiful cafeteria close by. "
United States
Johanna
The price is P5,356
P6,178 total
includes taxes & fees
Jun 8 - Jun 9
Residenza Fabroni
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (176 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is P6,736
P7,624 total
includes taxes & fees
May 28 - May 29
Abbadia Sicille Relais
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 P9,243
P10,311 total
includes taxes & fees
May 28 - May 29
Borgo Dolciano
Property entrance

Castello di Modanella

Castello di Modanella
Rapolano Terme
8.0 out of 10, Very Good, (17 reviews)
"To far out"
United States
Dennis
The price is P6,384
P9,457 total
includes taxes & fees
Jun 7 - Jun 8
Castello di Modanella
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (98 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 P10,201
P11,508 total
includes taxes & fees
May 26 - May 27
Meublé Il Riccio
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (140 reviews)
"Great location."
United States
James
The price is P11,128
P12,528 total
includes taxes & fees
Jun 11 - Jun 12
La Locanda di San Francesco
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 P8,460
P9,307 total
includes taxes & fees
May 26 - May 27
Residenza d'epoca Ca' de Principi
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 P4,059
P4,465 total
includes taxes & fees
May 26 - May 27
L'Antica Sosta
Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is P5,872
P6,746 total
includes taxes & fees
May 26 - May 27
DormiVeglia B&B
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (135 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is P7,409
P8,437 total
includes taxes & fees
May 26 - May 27
Bed & Breakfast Vicolo dell'Oste
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 P7,605
P8,508 total
includes taxes & fees
May 27 - May 28
La Piccola Locanda
Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (36 reviews)
"Time transported to the Renaissance at this beautiful, well-kept palazzo… Riccardo’s family did a truly amazing job restoring this place and the facilities are modern & without any discomfort."
American Samoa
Melissa Hyun Joo
The price is P12,124
P13,623 total
includes taxes & fees
Jun 3 - Jun 4
Delcorto Suites
Lunch and dinner served

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 P17,621
P19,669 total
includes taxes & fees
May 26 - May 27
Castello di Gargonza
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
"This is a fantastic hotel. Wonderful staff, an out standing fine dining restaurant, comfortable rooms and nice garden with pool. Loved it and can’t wait to go back."
Michael 2-night trip
Posted 9 hours ago
Monastero di Cortona Hotel & Spa

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 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 6 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.