Holiday Rentals in Ossaia

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30 Nov - 1 Dec
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1 Dec - 2 Dec
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5 Dec - 7 Dec
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12 Dec - 14 Dec

Holiday Rentals in Ossaia

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La Locanda di San Francesco

La Locanda di San Francesco

Montepulciano
9.8 out of 10, Exceptional, (130)
"Beautiful property nestled at the top of montepulciano. Very helpful owner Luca and unmatched hospitality! "
United States
Alizeh
The price is €151
includes taxes & fees
11 Dec - 12 Dec
La Locanda di San Francesco
Interior
Delcorto Suites

Delcorto Suites

Montepulciano
10.0 out of 10, Exceptional, (32)
"Exceptional service great building felt like a Medici!"
United States
gaetano
The price is €172
includes taxes & fees
2 Dec - 3 Dec
Delcorto Suites
Exterior
Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste

Montepulciano
9.6 out of 10, Exceptional, (127)
"Great hosts, central location "
United States
Alexander
The price is €112
includes taxes & fees
1 Dec - 2 Dec
Bed & Breakfast Vicolo dell'Oste
Lobby
Residenza Fabroni

Residenza Fabroni

Montepulciano
8.8 out of 10, Excellent, (93)
"We had a great stay! Beautiful on the roof top terrace!"
United States
Jennifer
The price is €84
includes taxes & fees
2 Dec - 3 Dec
Residenza Fabroni
Property entrance
Il Tosco

Il Tosco

Montepulciano
10.0 out of 10, Exceptional, (113)
"Stunning views. Excellent hostess! Fabulous breakfast!! Would definitely stay again if ever back"
Canada
stephen
The price is €302
includes taxes & fees
1 Dec - 2 Dec
Il Tosco
Deluxe Double Room | View from room
Affitacamere Maria Gabriella

Affitacamere Maria Gabriella

Pienza
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
Exterior
Meublé Il Riccio

Meublé Il Riccio

Montepulciano
9.8 out of 10, Exceptional, (86)
"Beautiful hotel."
United States
Helen
Meublé Il Riccio
View from room
Abbadia Sicille Relais

Abbadia Sicille Relais

4.0 star property
Trequanda
8.8 out of 10, Excellent, (163)
"We stayed there for 1 night our our way to Rome. BEAUTIFUL. Bed was very comfortable as well. 10/10 will recommend to everyone "
United States
Brittnay
The price is €71
includes taxes & fees
4 Dec - 5 Dec
Abbadia Sicille Relais
Daily buffet breakfast (EUR 10 per person)
DormiVeglia B&B

DormiVeglia B&B

Monte San Savino
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

San Michele al Borgo

Castiglion Fiorentino
9.8 out of 10, Exceptional, (9)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is €135
includes taxes & fees
9 Dec - 10 Dec
San Michele al Borgo
Exterior
Montecchio di Cortona

Montecchio di Cortona

Montecchio
9.0 out of 10, Wonderful, (2)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is €82
includes taxes & fees
31 Dec - 1 Jan 2026
Montecchio di Cortona
Exterior
L'Antica Sosta

L'Antica Sosta

Corciano
9.4 out of 10, Exceptional, (3)
"Molto accoglienti e gentili "
Italy
Valentina
The price is €61
includes taxes & fees
1 Dec - 2 Dec
L'Antica Sosta
Property grounds
La casa di Laura

La casa di Laura

Cortona Old Town
10.0 out of 10, Exceptional, (1)
"Best sleep I’ve had in a long time. Very quiet area. Beautiful views. Absolutely gorgeous. Water and coffee were provided. Clean. Bruno was very patient with us with the language barrier. We also had trouble getting to the place because we were not getting service on our phone till we connected to WiFi. Bruno met us and showed us where to park after showing us the way to the apartment. Very steep climb up to the apartment from the parking area, but Cortona is overall steep. You will climb up...
United States
Angie F.
The price is €192
includes taxes & fees
1 Dec - 2 Dec
La casa di Laura
Bar (on property)
La Piccola Locanda

La Piccola Locanda

Chiusi
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
1 bedroom, desk, iron/ironing board, WiFi
Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Old Town
10.0 out of 10, Exceptional, (3)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
The price is €120
includes taxes & fees
1 Dec - 2 Dec
Cortona Shabby Chic House<br>(Independent & balcony)
Outdoor pool, pool loungers
Borgo Dolciano

Borgo Dolciano

Chiusi
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 €122
includes taxes & fees
14 Dec - 15 Dec
Borgo Dolciano
Outdoor dining
Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!

Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!

Castel Rigone
10.0 out of 10, Exceptional, (3)
"The only thing this place could have that it doesn't is an infinity pool! We loved it here. It was a last minute booking and the host was super helpful. STUNNING views from the patio, and the lake is a short drive down the hill. Also, a very cool little town with restaurants just a two minute drive.Our favorite stays in Italy we're in these little remote towns. Soooo nice. "
United States
Adam H.
The price is €119
includes taxes & fees
1 Dec - 2 Dec
Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!
1 bedroom, travel cot, free WiFi
City / Village Apartment in Cortona with 1 bedrooms sleeps 2

City / Village Apartment in Cortona with 1 bedrooms sleeps 2

Cortona Old Town
10.0 out of 10, Exceptional, (6)
"This place was such a great find! So central and easily reachable. We really enjoyed our stay!"
United States
Julie R.
The price is €98
includes taxes & fees
1 Dec - 2 Dec
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Property grounds
Artisti del Cavallo Tourism

Artisti del Cavallo Tourism

Foiano della Chiana
8.4 out of 10, Very good, (24)
"Good house for one night. "
Germany
Heiner
The price is €82
includes taxes & fees
1 Dec - 2 Dec
Artisti del Cavallo Tourism
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
"Our arrival experience was less than stellar for a warm welcome to property. Front desk associate was very cold and accusatory of the situation we encountered outside of the property. We have traveled extensively and I expected better arrival experience. It all changed for the better when we finally got to our amazing suite and befriending two amazing individuals in the hotel bar. The roof top suite was absolutely amazing! The room is quiet, private and much larger than described on the site. We absolutely loved the room and the privacy. The rooftop suite is the best in the house! Claudio in the bar and Salvatore the sommelier are stellar to guests, they turned around the entire experience! I let them know what had happened upon arrival and they immediately got the GM to reach out to us. Lara, the GM is amazing and quickly made our experience turn into something so special, as we wanted! She is an incredible woman and turned our stay into an incredible experience! The breakfast is nothing less than wonderful and the service in their restaurants are so attentive and the food was delicious. Hands down, I would love to go back again. They certainly made things right by making our romantic stay, exactly what I wanted. They made us feel heard and valued and welcomed at this once in a lifetime experience. We made friends that we will cherish and memories that we will never forget! Claudio, Lara and Salvatore really made our stay exactly what we needed and wanted! "
heather 2-night trip
Posted 7 days ago
Monastero di Cortona Hotel & Spa

Find out more about Ossaia

Everything you need to know about Ossaia holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ossaia holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ossaia holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Ossaia holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ossaia. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ossaia holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ossaia holiday rentals we have selected for you start as low as €71 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ossaia rentals

At Expedia, we put the best Ossaia holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Ossaia rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ossaia holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ossaia. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

What are some of the best holiday rentals that Ossaia has to offer?

Farmhouse in the hills with panoramic view and swimming pool: This holiday home rental outside of Ossaia is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Ossaia?

With 8 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.