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Ossaia Vacation Rentals

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Ossaia vacation rentals

Lobby

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (23 reviews)
The price is AED 524
AED 594 total
includes taxes & fees
30 Aug - 31 Aug
B&B Piccolo Hotel
Property grounds

2. 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, (8 reviews)
"This place was such a great find! So central and easily reachable. We really enjoyed our stay!"
United States
Julie R.
The price is AED 398
AED 415 total
includes taxes & fees
1 Sep - 2 Sep
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Deluxe Apartment, City View | Soundproofing, iron/ironing board, WiFi (free)

3. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is AED 491
AED 553 total
includes taxes & fees
17 Sep - 18 Sep
CASA AMBRA
Apartment (1 Bedroom) | Front of property

4. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is AED 368
AED 422 total
includes taxes & fees
1 Sep - 2 Sep
Vicolo Della Scala Rooms - La Luna
Outdoor dining

5. Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is AED 268
AED 345 total
includes taxes & fees
30 Aug - 31 Aug
Holiday home with panoramic terrace ideal for families and couples
Dining

6. Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2 reviews)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is AED 336
AED 413 total
includes taxes & fees
31 Aug - 1 Sep
Montecchio di Cortona
Interior

7. La Finestra sul Teatro

La Finestra sul Teatro
Cortona Old Town
9.8 out of 10, Exceptional, (38 reviews)
"This was perfectly clean. The host was perfect."
United States
Michelle H.
The price is AED 555
AED 845 total
includes taxes & fees
2 Sep - 3 Sep
La Finestra sul Teatro
Junior Suite | Terrace/patio

8. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is AED 426
AED 485 total
includes taxes & fees
7 Sep - 8 Sep
Casale dell'Assiolo
Interior

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

Cortona Shabby Chic House<br>(Independent & balcony)
Cortona Old Town
10.0 out of 10, Exceptional, (3 reviews)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
The price is AED 526
AED 615 total
includes taxes & fees
30 Aug - 31 Aug
Cortona Shabby Chic House<br>(Independent & balcony)
Interior

10. La casa di Laura

La casa di Laura
Cortona Old Town
10.0 out of 10, Exceptional, (1 review)
"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 AED 383
AED 749 total
includes taxes & fees
28 Sep - 29 Sep
La casa di Laura
Pool

11. Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi

Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi
Cortona (AR)
9.0 out of 10, Wonderful, (2 reviews)
"Pros: Die Anlage strahlt einen wunderbaren nostalgischen Charme aus. Elisa hat sich hervorragend um uns gekümmert. Per Whatsapp wurden sämtliche Fragen in Kürze geklärt. Cons: Die Terrasse ist kaum zu nützen, da vor allem am Abend die Mückenplage unangenehm ist. Die Fenster und Türen der Wohnung haben alle Fliegen- und Mückengitter."
Germany
Anonymous traveler
The price is AED 934
AED 2,508 total
includes taxes & fees
6 Sep - 7 Sep
Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi
Property grounds

12. Cortonas Rooftop Nest

Cortonas Rooftop Nest
Cortona Old Town
10.0 out of 10, Exceptional, (12 reviews)
"Absolute gem of a property. Margherita is an excellent host as well!"
United States
Robin F.
The price is AED 686
AED 792 total
includes taxes & fees
31 Aug - 1 Sep
Cortonas Rooftop Nest
Exterior

13. 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 AED 496
AED 563 total
includes taxes & fees
1 Sep - 2 Sep
San Michele al Borgo
Exterior

14. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very Good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is AED 293
AED 340 total
includes taxes & fees
6 Sep - 7 Sep
Artisti del Cavallo Tourism
Private kitchen

15. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is AED 191
AED 285 total
includes taxes & fees
1 Sep - 2 Sep
Happy Nest Tuscany Between Florence and Rome
Classic Apartment, Vineyard View | Interior

16. Podere Tre Berte - The Sleeping Beauty

Podere Tre Berte - The Sleeping Beauty
Toscana
The price is AED 383
AED 421 total
includes taxes & fees
1 Sep - 2 Sep
Podere Tre Berte - The Sleeping Beauty
Property entrance

17. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (104 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 AED 298
AED 345 total
includes taxes & fees
30 Aug - 31 Aug
Residenza Fabroni
Interior

18. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (116 reviews)
"It was very well located ."
Canada
Marlenne
The price is AED 606
AED 684 total
includes taxes & fees
30 Aug - 31 Aug
Meublé Il Riccio
Courtyard

19. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay here! The hosts and staff were super warm and friendly. Breakfast had a wide choice and we liked the evening drinks set up too! The hotel doggies were definitely a highlight ☺️ we’d love to come back!"
United Kingdom
Shelby
The price is AED 956
AED 1,068 total
includes taxes & fees
1 Sep - 2 Sep
Fontelunga Hotel & Villas
Terrace/patio

20. 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 AED 602
AED 675 total
includes taxes & fees
1 Sep - 2 Sep
Abbadia Sicille Relais
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

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent
"Unforgetable experience in the middle of wine country in Tuscany. Higly recommended. the view from the property is amazing. Excellent full breakfast and clean rooms. Only minor complain is the air conditioning in a very hot august months."
Jacobo 2-night trip
Posted 18 hours ago
Relais Villa Grazianella - UNA Esperienze

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?

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome: This vacation home rental near Ossaia is located in a rural location and has an outdoor pool, a fireplace, 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. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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 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.