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Check prices for these dates

In two weeks
11 Sept - 13 Sept
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 Osceola holiday rentals

1. Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy
2.5 star property
Osceola
10.0 out of 10, Exceptional, (51 reviews)
"They are pet friendly and great spot for a get away"
United States
Safa
The price is £96
includes taxes & fees
27 Sept - 28 Sept
Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy
A compact kitchen with white cabinets, a microwave, and a refrigerator.

2. Chestnut on the square, unit B

Chestnut on the square, unit B
Osceola
9.8 out of 10, Exceptional, (30 reviews)
"Great place, very clean. "
United States
Evan B.
The price is £112
includes taxes & fees
6 Sept - 7 Sept
Chestnut on the square, unit B
A modern kitchen with white cabinets, a dining table with chairs, and a chandelier. There is a living area with a red sofa and a lamp.

3. The Chestnut on the Square Historic Loft A

The Chestnut on the Square Historic Loft A
Osceola
10.0 out of 10, Exceptional, (47 reviews)
"Great place to stay "
United States
Brandon J.
The price is £154
includes taxes & fees
6 Sept - 7 Sept
The Chestnut on the Square Historic Loft A
A wooden deck with wicker furniture, a metal building with a dark door, and a forested background.

4. 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, (30 reviews)
"Such a nice, quiet, secluded cabin! "
United States
Hailee W.
The price is £147
includes taxes & fees
3 Sept - 4 Sept
Secluded Hunting & Fishing cabin in the Woods - Osceola, MO
A house with a porch, surrounded by a grassy lawn and trees.

5. Cozy 2-bedroom Schoolhouse Cabin near Truman Lake access points

Cozy 2-bedroom Schoolhouse Cabin near Truman Lake access points
Osceola
10.0 out of 10, Exceptional, (1 review)
"Very quiet and peaceful. The interior was clean and updated. Nice living room with 3 love seats, which I think are also pull-out beds? And there is a card table with sturdy comfortable chairs that can seat maybe 6 people. There is a small, but very nice kitchen. Two bathrooms, each attached to its own bathroom, with the bathrooms also having a second door opening to the living room for convenience. Beds were comfortable, but just note for guests who are bigger or have mobility issues, the beds...
United States
Douglas H.
The price is £110
includes taxes & fees
1 Sept - 2 Sept
Cozy 2-bedroom Schoolhouse Cabin near Truman Lake access points
A group of people sitting around a campfire in a wooded area at night.

6. Charming Micro Cabin 4 in the heart of the Ozarks

Charming Micro Cabin 4 in the heart of the Ozarks
Osceola
The price is £75
includes taxes & fees
31 Aug - 1 Sept
Charming Micro Cabin 4 in the heart of the Ozarks
A single-story building with a garage door, a bench outside, and a gravel driveway.

7. Charming Micro Cabin 1 near Truman Lake in the Ozarks!

Charming Micro Cabin 1 near Truman Lake in the Ozarks!
Osceola
The price is £75
includes taxes & fees
30 Aug - 31 Aug
Charming Micro Cabin 1 near Truman Lake in the Ozarks!
A group of people sitting around a campfire in a wooded area at night.

8. Cozy micro cabin 3 near Truman Lakes in the Ozarks

Cozy micro cabin 3 near Truman Lakes in the Ozarks
Osceola
The price is £75
includes taxes & fees
30 Aug - 31 Aug
Cozy micro cabin 3 near Truman Lakes in the Ozarks

9. Bunkhouse Cabin near Truman Lake in the Ozarks!

Bunkhouse Cabin near Truman Lake in the Ozarks!
Osceola
The price is £95
includes taxes & fees
29 Aug - 30 Aug
Bunkhouse Cabin near Truman Lake in the Ozarks!
A compact room with a kitchenette, a bed, a chair, and a ceiling fan.

10. Cozy studio shotgun apartment in the heart of the Ozarks

Cozy studio shotgun apartment in the heart of the Ozarks
Osceola
The price is £79
includes taxes & fees
31 Aug - 1 Sept
Cozy studio shotgun apartment in the heart of the Ozarks
A single-story building with a garage door, a bench outside, and a gravel driveway.

11. Charming Micro cabin 2 in the heart of the Ozarks

Charming Micro cabin 2 in the heart of the Ozarks
Osceola
The price is £100
includes taxes & fees
8 Sept - 9 Sept
Charming Micro cabin 2 in the heart of the Ozarks
A cozy living room with a wooden ceiling, a ceiling fan, a large flat-screen TV, a sofa, and a coffee table.

12. Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.

Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.
Deepwater
10.0 out of 10, Exceptional, (49 reviews)
"Perfect getaway to relax. We enjoyed our trip and will be booking again!"
United States
Cynthia M.
The price is £170
includes taxes & fees
3 Sept - 4 Sept
Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.
A modern kitchen with white cabinets, a black refrigerator, and a marble countertop. There is a black sofa with red and yellow cushions in the living area.

13. 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, (23 reviews)
"Great Place to stay!"
United States
John F.
The price is £102
includes taxes & fees
30 Aug - 31 Aug
2-bedroom vacation home just 8 minutes from Stockton Lake
A wooden interior with a large barrel, a table with a vase, and a view of a lake through glass doors.

14. Romantic Country Cabin at Lakeview by Sue

Romantic Country Cabin at Lakeview by Sue
Appleton City
10.0 out of 10, Exceptional, (14 reviews)
"Wonderful stay, so beautiful! "
United States
Anna G.
The price is £131
includes taxes & fees
30 Aug - 31 Aug
Romantic Country Cabin at Lakeview by Sue
A row of cabins with wooden decks and stairs leading to the entrance.

15. Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.2 out of 10, Very good, (23 reviews)
"Nice place to stay "
United States
Sam
The price is £77
includes taxes & fees
30 Aug - 31 Aug
Hickory Hollow Resort
A snow-covered landscape with several wooden houses, a barbecue grill, and a wooden bench.

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

Water’s Edge Cabin: King & Queen Beds (Cabin 4)
Stockton
9.8 out of 10, Exceptional, (10 reviews)
"The cabin was perfect! My daughter and I enjoyed our mini vacation get away."
United States
connie a.
The price is £155
includes taxes & fees
30 Aug - 31 Aug
Water’s Edge Cabin: King & Queen Beds (Cabin 4)
A wooden interior with a sliding glass door leading to an outdoor deck.

17. Cute Family Cabin at Lakeview by Sue

Cute Family Cabin at Lakeview by Sue
Appleton City
10.0 out of 10, Exceptional, (8 reviews)
"This place was fantastic. We will return again next year. "
United States
Lee C.
The price is £141
includes taxes & fees
30 Aug - 31 Aug
Cute Family Cabin at Lakeview by Sue
A park with a playground, a bench, a lamppost, and a view of a lake.

18. Cozy Home w/ Doggy Fence

Cozy Home w/ Doggy Fence
Warsaw
9.0 out of 10, Wonderful, (70 reviews)
"Host was easy to contact/ house was clean."
United States
Prentiss E.
The price is £138
includes taxes & fees
1 Sept - 2 Sept
Cozy Home w/ Doggy Fence
A small, single-story building with a porch and a fenced yard.

19. Grandma's Cabin at Stockton Lake, Stockton Missouri.

Grandma's Cabin at Stockton Lake, Stockton Missouri.
Stockton
9.6 out of 10, Exceptional, (59 reviews)
"This is a great place to stay country setting kinda reminded me of the old day like little house on the prairie we will be staying there agean this summer great people we had storms and they told us where to go so that was great."
United States
Jessica B.
The price is £108
includes taxes & fees
30 Aug - 31 Aug
Grandma's Cabin at Stockton Lake, Stockton Missouri.
A compact kitchen with wooden cabinets, a white refrigerator, a stove, and a sink.

20. Cabin 3 - Reel and Trigger

Cabin 3 - Reel and Trigger
Tom Township
9.4 out of 10, Exceptional, (3 reviews)
"We enjoy our stay. The location is awesome. No hassles."
United States
April G.
The price is £119
includes taxes & fees
30 Aug - 31 Aug
Cabin 3 - Reel and Trigger
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

Westbridge Inn and Suites

Westbridge Inn and Suites

8/10 Good
"Everything was great for the most part, some of the other visitors were a little shady that’s all."
Samuel 3-night trip
Posted 3 days ago
Westbridge Inn and Suites

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, apart-hotels, 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 £77 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?

GRANDMA'S GET-A-WAY (Water Front property ) WIFI. Private covered one bay dock.: This holiday home rental outside of Osceola is located on a lake, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Osceola?

Truman Reservoir and Harry S Truman Reservoir are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Osceola Cheese. Lilleys Island and Crowes Crossing Public Use 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.