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Ossaia Vacation Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Ossaia vacation rentals

Outdoor dining

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is SAR 269
SAR 346 total
includes taxes & fees
15 Jul - 16 Jul
Holiday home with panoramic terrace ideal for families and couples
Iron/ironing board, WiFi, bed sheets

Double room with private bathroom in the countryside 5 minutes from Montepulciano

Double room with private bathroom in the countryside 5 minutes from Montepulciano
Toscana
The price is SAR 462
SAR 692 total
includes taxes & fees
16 Jul - 17 Jul
Double room with private bathroom in the countryside 5 minutes from Montepulciano
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (103 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is SAR 334
SAR 385 total
includes taxes & fees
15 Jul - 16 Jul
Residenza Fabroni
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 SAR 454
SAR 508 total
includes taxes & fees
15 Jul - 16 Jul
La Piccola Locanda
Outdoor dining

Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is SAR 329
SAR 457 total
includes taxes & fees
16 Jul - 17 Jul
Dolce Casa 2 by Tiny Away
Private kitchen

Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is SAR 346
SAR 440 total
includes taxes & fees
15 Jul - 16 Jul
Happy Nest Tuscany Between Florence and Rome
1 bedroom, WiFi, bed sheets

Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is SAR 353
SAR 482 total
includes taxes & fees
16 Jul - 17 Jul
Dolce Casa 1 by Tiny Away
1 bedroom, iron/ironing board, WiFi

Boutique Apartment Natura

Boutique Apartment Natura
Chiusi
10.0 out of 10, Exceptional, (1 review)
"Great location and very clean!"
Canada
Shelley
The price is SAR 340
SAR 415 total
includes taxes & fees
15 Jul - 16 Jul
Boutique Apartment Natura
Outdoor dining

Deluxe room Cartazucchero in the heart of Arezzo

Deluxe room Cartazucchero in the heart of Arezzo
Arezzo Centro Storico
10.0 out of 10, Exceptional, (3 reviews)
"From all the places we stayed during our 13-day trip to Italy, this was by far our favorite. Fabio was incredibly communicative and friendly right from the start, sending us clear instructions on how to get there. He greeted us at the door with such warmth that it truly felt like we were staying with family. The room was spotless, beautifully decorated, and generously stocked with water, cookies, pastries, and other treats. It had the comfort and attention to detail of a hotel, yet the warmth of...
United States
Hector
The price is SAR 328
SAR 361 total
includes taxes & fees
15 Jul - 16 Jul
Deluxe room Cartazucchero in the heart of Arezzo
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 SAR 242
SAR 266 total
includes taxes & fees
29 Jul - 30 Jul
L'Antica Sosta
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 SAR 505
SAR 556 total
includes taxes & fees
15 Jul - 16 Jul
Residenza d'epoca Ca' de Principi
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (178 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is SAR 832
SAR 928 total
includes taxes & fees
19 Jul - 20 Jul
Abbadia Sicille Relais
Apartment (1 Bedroom) | Front of property

Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is SAR 343
SAR 395 total
includes taxes & fees
21 Jul - 22 Jul
Vicolo Della Scala Rooms - La Luna
Junior Suite | Terrace/patio

Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is SAR 500
SAR 567 total
includes taxes & fees
9 Aug - 10 Aug
Casale dell'Assiolo
Outdoor dining

Living suite Verdeconiglio in the heart of Arezzo

Living suite Verdeconiglio in the heart of Arezzo
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
"It was a beautiful and quiet part of town and was very close to everything. The property manager spoke pretty good English which made everything much easier. It is a beautiful comforting and clean stay in the heart of Arezzo. Thank you. Era una zona bellissima e tranquilla della città, vicinissima a tutto. Il gestore parlava un ottimo inglese, il che ha reso tutto molto più semplice. È stato un soggiorno splendido, confortevole e pulito nel cuore di Arezzo. Grazie."
United States
Andrew T.
The price is SAR 374
SAR 411 total
includes taxes & fees
17 Jul - 18 Jul
Living suite Verdeconiglio in the heart of Arezzo
Interior

MariSanti House - Three Bedroom Apartment, Sleeps 6

MariSanti House - Three Bedroom Apartment, Sleeps 6
Arezzo
The price is SAR 588
SAR 930 total
includes taxes & fees
27 Jul - 28 Jul
MariSanti House - Three Bedroom Apartment, Sleeps 6
Exterior

Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
The price is SAR 381
SAR 680 total
includes taxes & fees
19 Jul - 20 Jul
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (114 reviews)
"It was very well located ."
Canada
Marlenne
The price is SAR 609
SAR 687 total
includes taxes & fees
15 Jul - 16 Jul
Meublé Il Riccio
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (145 reviews)
"Great location."
United States
James
The price is SAR 550
SAR 622 total
includes taxes & fees
6 Aug - 7 Aug
La Locanda di San Francesco
Terrace/patio

Charming bungalow with whirlpool in Tuscany: peace, nature and comfort

Charming bungalow with whirlpool in Tuscany: peace, nature and comfort
Antria
The price is SAR 577
SAR 679 total
includes taxes & fees
15 Jul - 16 Jul
Charming bungalow with whirlpool in Tuscany: peace, nature and comfort
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
"The food was amazing in the hotel. Staff was amazing. We felt at home from the moment we walked in. The amenities were wonderful."
Darren 2-night trip
Posted 13 hours ago
Monastero di Cortona Hotel & Spa

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?

La Dolce Collina: You might like this vacation home rental near Ossaia. It is located in a rural location and has a garden, a hot tub, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and kitchenware.

How many vacation rentals are there in Ossaia?

With 7 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 Cortona Cathedral.

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.