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Osceola Holiday Rentals

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Our top choices for Osceola holiday rentals

Secluded Hunting & Fishing cabin in the Woods - Osceola, MO

Secluded Hunting & Fishing cabin in the Woods - Osceola, MO
Osceola
9.8 out of 10, Exceptional, (20)
"Great secluded Cabin with all ammenities you need, very clean and well kept would definetly recommend!"
United States
william
The price is NZ$336
includes taxes & fees
11 Dec - 12 Dec
Secluded Hunting & Fishing cabin in the Woods - Osceola, MO

Historic Commercial Hotel(Est. 1868)Tom Mix Suite

Historic Commercial Hotel(Est. 1868)Tom Mix Suite
Osceola
9.8 out of 10, Exceptional, (17)
"Great place. We loved the historical signs and display cases with artifacts around the hotel. The celebration in the town square was a nice bonus. Very quiet and quaint. I wish we'd have had more time to do a little fishing."
United States
B P.
The price is NZ$193
includes taxes & fees
11 Dec - 12 Dec
Historic Commercial Hotel(Est. 1868)Tom Mix Suite

Chestnut on the square, unit B

Chestnut on the square, unit B
Osceola
10.0 out of 10, Exceptional, (25)
"Great stay, very clean & comfortable. Perfect for our overnight stay to be close to Bartle scout camp. Quick response to questions when we arrived. "
United States
Andrea G.
The price is NZ$226
includes taxes & fees
17 Dec - 18 Dec
Chestnut on the square, unit B

Charming Micro Cabin 4 in the heart of the Ozarks

Charming Micro Cabin 4 in the heart of the Ozarks
2.0 star property
Osceola
The price is NZ$138
includes taxes & fees
11 Dec - 12 Dec
Charming Micro Cabin 4 in the heart of the Ozarks

The Chestnut on the Square Historic Loft A

The Chestnut on the Square Historic Loft A
Osceola
10.0 out of 10, Exceptional, (38)
"Very nice place to stay with plenty of room. Really easy to get to and beautiful place."
United States
Craig S.
The price is NZ$293
includes taxes & fees
17 Dec - 18 Dec
The Chestnut on the Square Historic Loft A

Cozy 2-bedroom Schoolhouse Cabin near Truman Lake access points

Cozy 2-bedroom Schoolhouse Cabin near Truman Lake access points
2.0 star property
Osceola
The price is NZ$201
includes taxes & fees
8 Jan - 9 Jan 2026
Cozy 2-bedroom Schoolhouse Cabin near Truman Lake access points

Cozy studio shotgun apartment in the heart of the Ozarks

Cozy studio shotgun apartment in the heart of the Ozarks
2.0 star property
Osceola
The price is NZ$145
includes taxes & fees
11 Dec - 12 Dec
Cozy studio shotgun apartment in the heart of the Ozarks

Cozy micro cabin 3 near Truman Lakes in the Ozarks

Cozy micro cabin 3 near Truman Lakes in the Ozarks
2.0 star property
Osceola
The price is NZ$138
includes taxes & fees
11 Dec - 12 Dec
Cozy micro cabin 3 near Truman Lakes in the Ozarks

Charming Micro Cabin 1 near Truman Lake in the Ozarks!

Charming Micro Cabin 1 near Truman Lake in the Ozarks!
2.0 star property
Osceola
The price is NZ$138
includes taxes & fees
11 Dec - 12 Dec
Charming Micro Cabin 1 near Truman Lake in the Ozarks!

Bunkhouse Cabin near Truman Lake in the Ozarks!

Bunkhouse Cabin near Truman Lake in the Ozarks!
2.0 star property
Osceola
The price is NZ$173
includes taxes & fees
11 Dec - 12 Dec
Bunkhouse Cabin near Truman Lake in the Ozarks!

Charming Micro cabin 2 in the heart of the Ozarks

Charming Micro cabin 2 in the heart of the Ozarks
2.0 star property
Osceola
The price is NZ$139
includes taxes & fees
24 Dec - 25 Dec
Charming Micro cabin 2 in the heart of the Ozarks

Water’s Edge Cabin: King & Queen Beds (Cabin 4)

Water’s Edge Cabin: King & Queen Beds (Cabin 4)
Stockton
10.0 out of 10, Exceptional, (6)
"Great spot "
United States
Jacob
The price is NZ$293
includes taxes & fees
11 Dec - 12 Dec
Water’s Edge Cabin: King & Queen Beds (Cabin 4)

Grandma's Cabin at Stockton Lake, Stockton Missouri.

Grandma's Cabin at Stockton Lake, Stockton Missouri.
Stockton
9.8 out of 10, Exceptional, (54)
"We enjoyed our stay. It was peaceful and quiet. "
United States
Melanie
The price is NZ$219
includes taxes & fees
12 Dec - 13 Dec
Grandma's Cabin at Stockton Lake, Stockton Missouri.

Charming 3-bedroom cabin in delightful Stockton with WiFi, AC,

Charming 3-bedroom cabin in delightful Stockton with WiFi, AC,
2.0 star property
Stockton, MO 65785
9.2 out of 10, Wonderful, (28)
"Overall we really liked the property."
United States
Jessica W.
The price is NZ$193
includes taxes & fees
15 Dec - 16 Dec
Charming 3-bedroom cabin in delightful Stockton with WiFi, AC,

Cute Family Cabin at Lakeview by Sue

Cute Family Cabin at Lakeview by Sue
Appleton City
10.0 out of 10, Exceptional, (8)
"Beautiful and peaceful place. Very clean and comfortable. "
United States
Harry S.
The price is NZ$327
includes taxes & fees
11 Dec - 12 Dec
Cute Family Cabin at Lakeview by Sue

Romantic Country Cabin at Lakeview by Sue

Romantic Country Cabin at Lakeview by Sue
Appleton City
10.0 out of 10, Exceptional, (10)
"Wonderful stay, so beautiful! "
United States
Anna G.
The price is NZ$303
includes taxes & fees
11 Dec - 12 Dec
Romantic Country Cabin at Lakeview by Sue

Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.4 out of 10, Very good, (13)
"Our cabin was clean, comfortable and affordable. The check-in was effortless and we had no issues with the stay. I would recommend the place to friends and family traveling through the area."
United States
Terry
The price is NZ$181
includes taxes & fees
8 Jan - 9 Jan 2026
Hickory Hollow Resort

The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown

The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown
Clinton
9.8 out of 10, Exceptional, (19)
"Needed a place to overnight during a fishing trip. Perfect for us. "
United States
moree30 m.
The price is NZ$274
includes taxes & fees
11 Dec - 12 Dec
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown

2-bedroom vacation home just 8 minutes from Stockton Lake

2-bedroom vacation home just 8 minutes from Stockton Lake
Humansville
10.0 out of 10, Exceptional, (12)
"An outstanding place to stay, and such lovely people to host! Seriously, they were extremely accommodating and so amazing "
United States
James K.
The price is NZ$221
includes taxes & fees
11 Dec - 12 Dec
2-bedroom vacation home just 8 minutes from Stockton Lake
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 Osceola Hotel Reviews

Find out more about Osceola

Everything you need to know about Osceola 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 Osceola holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Osceola holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Osceola holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osceola. 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 Osceola 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 Osceola holiday rentals we have selected for you start as low as NZ$193 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Osceola rentals

At Expedia, we put the best Osceola 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 Osceola 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 Osceola 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 Osceola. 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

Can I find a holiday rental in Osceola?

Yes, there are holiday rentals in Osceola close to Osceola Cheese, 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 Osceola has to offer?

Lake Cottage Getaway at Pomme De Terre Lake: This holiday home rental outside of Osceola is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Osceola?

Harry S Truman Reservoir and Lilleys Island are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Osceola Cheese. Crowes Crossing Public Use Area and Gallinipper Creek State Wildlife Area are other places to visit while you're in town.

What are holiday rentals like in Osceola?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osceola. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for family trips.