Ossaia Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Ossaia

Exterior
Wonderful villa at the foot of Cortona with private pool and unforgettable views

Wonderful villa at the foot of Cortona with private pool and unforgettable views

Cortona
9.4 out of 10, Exceptional, (3)
"The casale is beautiful, well located and maintained.It met our expectations and provided the perfect location for our Easter holidays.The kitchen is beautiful, as well as the outside court. Wonderful exposure to the sun provides the right background for unforgettable aperitifs surrounded by nature.Some minor flaws coming with old houses in countryside, like a very stinky bathroom in the ground floor. Unnecessary amount of random decorations not seen in pictures (Mexican hat hanged on a wall in...
United States
Kevin G.
Wonderful villa at the foot of Cortona with private pool and unforgettable views
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 ￥10,976
￥12,606 total
includes taxes & fees
Dec 3 - Dec 4
Abbadia Sicille Relais
Pool
Farmhouse in the hills with panoramic view and swimming pool

Farmhouse in the hills with panoramic view and swimming pool

Ristonchia
9.6 out of 10, Exceptional, (75)
"Pros: Location Excellent pool Fantastic views Cons: Very, very outdated kitchen. Limited privacy due to people staying in outbuildings some of the time. A (not unfriendly) cat that's fed at the property and it seems to be assumed that guests will do this. There's a strong smell of cats in the kitchen and the area immediately outside it. Doors can't be left open to ventilate the property when using the pool as the cat may get inside. No consumables apart from toilet roll and cat food: not so...
United Kingdom
Calum S.
Farmhouse in the hills with panoramic view and swimming pool
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 ￥12,959
￥14,965 total
includes taxes & fees
Nov 12 - Nov 13
Residenza Fabroni
Deluxe Apartment, 2 Bedrooms, Balcony | Free WiFi, bed sheets
Bellarmino Boutique Apartments

Bellarmino Boutique Apartments

Montepulciano
The price is ￥12,121
￥14,043 total
includes taxes & fees
Nov 11 - Nov 12
Bellarmino Boutique Apartments
Outdoor dining
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

chiusi
10.0 out of 10, Exceptional, (54)
"Our group of 15 thoroughly enjoyed our stay. The communication prior to and during the visit was excellent. The villa is stunning and HUGE and the grounds are magnificent. One day of our trip was spent just relaxing on the property and it was precious time well spent. "
United States
Mindy K.
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Property entrance
Il Tosco

Il Tosco

Montepulciano
10.0 out of 10, Exceptional, (112)
"The people here are authentic and welcoming! The building, rooms and facilities are gorgeous! One of our most beautiful stays in our many trips to Italy "
United States
Michael
The price is ￥35,664
￥39,941 total
includes taxes & fees
Nov 18 - Nov 19
Il Tosco
Exterior
Il Poggio dell'Eremita

Il Poggio dell'Eremita

Sinalunga
10.0 out of 10, Exceptional, (57)
"Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular."
United States
Vivian K.
The price is ￥20,921
￥24,470 total
includes taxes & fees
Nov 11 - Nov 12
Il Poggio dell'Eremita
Outdoor pool
Villa Graziella, Romantic Perugia

Villa Graziella, Romantic Perugia

La Valle
9.6 out of 10, Exceptional, (7)
"Perfekte Lage um Umbrien zu erkunden und einen Abstecher in die Toskana zu machen. Die Unterkunft war wie beschrieben. Die Kommunikation mit dem Vermieter lief gut. Kleiner Makel, bei einem Aufenthalt von 14 Tagen sollte zur Hälfte der Zeit die Bettwäsche und die Handtücher gewechselt werden. In der 2.Woche waren die Nächte relativ kühl (15), da hat die Überdecke zum Laken gefehlt. Sonst alles prima."
Germany
Joerg R.
The price is ￥17,248
￥29,847 total
includes taxes & fees
Nov 11 - Nov 12
Villa Graziella, Romantic Perugia
Standard Room | Exterior
Osteria del Borgo

Osteria del Borgo

Montepulciano
9.0 out of 10, Wonderful, (156)
"Staff and location were both excellent."
United States
Nicholas
Osteria del Borgo
Outdoor dining
Luxury Cortona view hilltop Villa

Luxury Cortona view hilltop Villa

cortona
10.0 out of 10, Exceptional, (50)
"Perfect location for day trips covering so many of the hilltop towns. Perfect accommodation for a group of 12 friends as each bedroom has it’s own bathroom.Perfect Villa for relaxing at home coffee every morning, lying by the pool and dinner watching the incredible sunsets.Perfect hosts. Denise takes care of everything while you are at the villa including cooking us a wonderful dinner. Mieke answered all our questions prior to our arrival very promptly. She has set the villa up perfectly and...
Australia
Belinda P.
Luxury Cortona view hilltop Villa
Property grounds
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv

Beautiful renovated stone villa - private pool,park,air conditioning,smart tv

AREZZO
9.8 out of 10, Exceptional, (35)
"Great location if you are trying to see Tuscany. The owners are the nicest people and very helpful. The house was fine for 4 of us with room to spare. Beautiful grounds, terrific, clean pool. Everything worked and everyone did their best to make us at home. It is just outside a small village so very quiet. You need a car to get around. Felt very safe --gated and secure. Would love to go back! "
United States
Tracy R.
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv
Exterior
Casina in authentic Tuscany

Casina in authentic Tuscany

Cortona
9.8 out of 10, Exceptional, (68)
"We had a lovely stay at the Casina, thank you to the family for such a welcome."
United Kingdom
David B.
Casina in authentic Tuscany
Pool
Villa La Pieve - Nine Bedroom Villa, Sleeps 20

Villa La Pieve - Nine Bedroom Villa, Sleeps 20

Città della Pieve
9.6 out of 10, Exceptional, (9)
"Amazing hospitality and a spotless, comfortable space."
United States
VISINESCU I.
Villa La Pieve - Nine Bedroom Villa, Sleeps 20
Interior
Delcorto Suites

Delcorto Suites

Montepulciano
10.0 out of 10, Exceptional, (32)
"Everything is great. The family owns the property over 600 years. Great breakfast, fabulous suite. "
United States
Liping
The price is ￥27,048
￥30,463 total
includes taxes & fees
Nov 12 - Nov 13
Delcorto Suites
Fridge, microwave, oven, stovetop
Charming House in the heart of Montepulciano

Charming House in the heart of Montepulciano

Montepulciano
9.8 out of 10, Exceptional, (64)
"The home was charming, spacious, and perfectly located. The host was responsive and helpful, making our stay comfortable and easy. A perfect spot to experience Tuscany—highly recommend!"
United States
Hank T.
Charming House in the heart of Montepulciano
Outdoor pool
Villa with private pool, air conditioning near wineries at 3km from village

Villa with private pool, air conditioning near wineries at 3km from village

CHIANCIANO terme
9.4 out of 10, Exceptional, (46)
"Thank you for your amazing hospitality and sharing your beautiful space with us. We felt welcomed and at home the entire time we were here. We enjoyed exploring all the Tuscan towns and enthralled by the beauty of the countryside. The pool was a favourite for our children and we loved seeing the different wildlife; porcupines, wild boars, and coyotes. The dinner that Leonardo cooked for us was an absolute highlight and HIGHLY recommend this to any other guests who wish to indulge. Thank you so...
Canada
Kevin H.
Villa with private pool, air conditioning near wineries at 3km from village
Outdoor pool
Villa with private pool, 7bedrooms, in Tuscan country between Cortona and Arezzo

Villa with private pool, 7bedrooms, in Tuscan country between Cortona and Arezzo

Arezzo
10.0 out of 10, Exceptional, (45)
"This property is just beautiful. One of the best I have ever stayed at. Everyone loved it. The location (right next to a lovely winery) couldn’t be better. Plenty of parking and ample space for our group. Hope to come back and stay again!"
United States
Deepak M.
Villa with private pool, 7bedrooms, in Tuscan country between Cortona and Arezzo
Outdoor pool
Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo

Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo

Arezzo
10.0 out of 10, Exceptional, (18)
"The property had beautiful gardens, well appointed apartments and a gracious and always helpful host. Children enjoyed the pool a great deal during hot afternoons. Conveniently located for day trips by train or car to Florence and historic and scenic hill towns."
United States
John N.
The price is ￥299,884
￥414,515 total
includes taxes & fees
Dec 7 - Dec 8
Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo
Fridge, microwave, oven, stovetop
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)

Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)

Arezzo Centro Storico
10.0 out of 10, Exceptional, (133)
"Wonderful location in Arezzo. The home itself is Amazing, Beautiful, Historic yet with Modern conveniences. Stefano, your host is so accommodating, incredibly helpful and is sure to make your stay perfect. If we could give it more ⭐️ stars we would!!"
United States
Pamela F.
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
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

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly "
Melodee 1-night trip
Posted 4 days ago
Villa di Piazzano - Small Luxury Hotel of the World

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:

  • View our selection of featured holiday rentals in Ossaia
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Look no further and take a look at our great range of rental properties in Ossaia!

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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.

What are some of the best vacation home rentals in Ossaia?

Farmhouse in the hills with panoramic view and swimming pool: This vacation home rental near Ossaia is located in a rural location and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Ossaia?

With 8 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.