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Ossaia Vacation Rentals

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Ossaia vacation rentals

An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.4 out of 10, Exceptional, (26 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
$138 nightly
The price is $157
Oct 25 - Oct 26
Total with taxes and fees
B&B Piccolo Hotel
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

2. CASA AMBRA

CASA AMBRA
Cortona Old Town
$215 nightly
The price is $239
Nov 20 - Nov 21
Total with taxes and fees
CASA AMBRA
A building entrance with a number '10' sign, a stone staircase, and a potted plant with pink flowers.

3. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
9.8 out of 10, Exceptional, (9 reviews)
"Nice property"
United States
Joseph
$105 nightly
The price is $109
Nov 3 - Nov 4
Total with taxes and fees
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

4. 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
$131 nightly
The price is $148
Nov 13 - Nov 14
Total with taxes and fees
San Michele al Borgo
Pool

5. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (41 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
$74 nightly
The price is $89
Nov 16 - Nov 17
Total with taxes and fees
iConic Wellness Resort
A park with picnic tables, a playground, and a gravel path.

6. Vacation home with a panoramic terrace, ideal for families and couples

Vacation home with a panoramic terrace, ideal for families and couples
Cortona
$91 nightly
The price is $91
Oct 26 - Oct 27
Total with taxes and fees
Vacation home with a panoramic terrace, ideal for families and couples
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

7. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
$75 nightly
The price is $87
Oct 29 - Oct 30
Total with taxes and fees
Artisti del Cavallo Tourism
A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

8. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
$71 nightly
The price is $75
Oct 25 - Oct 26
Total with taxes and fees
Happy Nest Tuscany Between Florence and Rome
Dining

9. 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.
$109 nightly
The price is $109
Oct 29 - Oct 30
Total with taxes and fees
Montecchio di Cortona
A staircase with two lit lanterns on the wall.

10. 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
$159 nightly
The price is $162
Oct 27 - Oct 28
Total with taxes and fees
Cortona Shabby Chic House<br>(Independent & Balcony)
A balcony with a clear view of a distant landscape, a stone building, and a glass of orange juice.

11. 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.
$192 nightly
The price is $195
Nov 8 - Nov 9
Total with taxes and fees
Cortonas Rooftop Nest
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

12. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay!"
Canada
Brian
$274 nightly
The price is $306
Oct 27 - Oct 28
Total with taxes and fees
Fontelunga Hotel & Villas
A bakery display with various pastries and desserts.

13. La Piccola Locanda

La Piccola Locanda
Chiusi
8.0 out of 10, Very good, (14 reviews)
"Very homey and wonderful people! We loved the restaurant below."
United States
autumn
$109 nightly
The price is $123
Oct 30 - Oct 31
Total with taxes and fees
La Piccola Locanda
A historic building with a tower, a courtyard, and a well-lit entrance.

14. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
$71 nightly
The price is $81
Nov 23 - Nov 24
Total with taxes and fees
Abbadia Sicille Relais
A spa area with a stone-walled arch, a hot tub, and a small window.

15. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (30 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
$107 nightly
The price is $122
Nov 8 - Nov 9
Total with taxes and fees
DormiVeglia B&B
A building with a stone facade, multiple windows, and a balcony.

16. Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
Cortona
10.0 out of 10, Exceptional, (1 review)
"Pros: il luogo che ci circondava rilassante ottimo. Cons: nulla come dicevo luogo ottimo."
Italy
Anonymous traveler
$262 nightly
The price is $268
Oct 25 - Oct 26
Total with taxes and fees
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
A patio area with outdoor seating, potted plants, and a view of the landscape.

17. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (74 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
$117 nightly
The price is $133
Oct 28 - Oct 29
Total with taxes and fees
Affitacamere Maria Gabriella
A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

18. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
$109 nightly
The price is $109
Oct 25 - Oct 26
Total with taxes and fees
Dolce Casa 2 by Tiny Away
A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

19. 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
$177 nightly
The price is $181
Oct 25 - Oct 26
Total with taxes and fees
Double room with private bathroom in the countryside, 5 minutes from Montepulciano
A nighttime view of a building with a staircase leading to a door, surrounded by greenery and a well-lit pathway.

20. Borgo Dolciano

Borgo Dolciano
Chiusi
9.0 out of 10, Wonderful, (26 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
$149 nightly
The price is $166
Oct 25 - Oct 26
Total with taxes and fees
Borgo Dolciano
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

Nuovo Etruria Resort

Nuovo Etruria Resort

8/10 Good
"When we arrived the gate to the hotel was locked. Called the hotel and then a person drove up and helped us to check in. He was very nice. The hotel is very old, but a decent place to stay for a night."
John 1-night trip
Posted 2 days ago
Nuovo Etruria Resort

Find out more about Ossaia

Everything you need to know about Ossaia vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ossaia vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ossaia vacation 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 low season months. For more hustle and bustle, you may prefer to visit Ossaia in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $62 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ossaia rentals

At Expedia, we put the best Ossaia vacation 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 vacation.

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 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.