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Osceola Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Osceola holiday rentals

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

Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy
2.5 star property
Osceola
9.6 out of 10, Exceptional, (78 reviews)
"Loved this location!! Will definitely revisit."
United States
Carmen
The price is NZ$232
includes taxes & fees
2 Dec - 3 Dec
Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy
A wooden deck with wicker furniture, a metal building with a dark door, and a forested background.

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

Secluded Hunting & Fishing cabin in the Woods - Osceola, MO
Osceola
10.0 out of 10, Exceptional, (33 reviews)
"Great place! Decorated so cute! Everything you need. Enjoyed the fire pit & rustic feel to the stay! Very outdoorsy location with all the amenities inside!"
United States
Kelly F.
The price is NZ$393
includes taxes & fees
4 Nov - 5 Nov
Secluded Hunting & Fishing cabin in the Woods - Osceola, MO
A compact kitchen with white cabinets, a microwave, and a refrigerator.

3. Chestnut on the square, unit B

Chestnut on the square, unit B
Osceola
9.8 out of 10, Exceptional, (31 reviews)
"Enjoyed our stay"
United States
tricia
The price is NZ$299
includes taxes & fees
9 Nov - 10 Nov
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.

4. The Chestnut on the Square Historic Loft A

The Chestnut on the Square Historic Loft A
Osceola
10.0 out of 10, Exceptional, (50 reviews)
"Great place to stay "
United States
Brandon J.
The price is NZ$374
includes taxes & fees
10 Nov - 11 Nov
The Chestnut on the Square Historic Loft A
A cozy living room with a wooden ceiling, a ceiling fan, a large flat-screen TV, a sofa, and a coffee table.

5. 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, (51 reviews)
"Perfect getaway to relax. We enjoyed our trip and will be booking again!"
United States
Cynthia M.
The price is NZ$386
includes taxes & fees
26 Nov - 27 Nov
Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.
A row of cabins with wooden decks and stairs leading to the entrance.

6. Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.2 out of 10, Very good, (27 reviews)
"Nice place to stay "
United States
Sam
The price is NZ$205
includes taxes & fees
14 Nov - 15 Nov
Hickory Hollow Resort
A wooden interior with a large barrel, a table with a vase, and a view of a lake through glass doors.

7. 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 NZ$284
includes taxes & fees
4 Nov - 5 Nov
Romantic Country Cabin at Lakeview by Sue
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.

8. 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, (25 reviews)
"Great Place to stay!"
United States
John F.
The price is NZ$226
includes taxes & fees
11 Nov - 12 Nov
2-bedroom vacation home just 8 minutes from Stockton Lake
A wooden interior with a sliding glass door leading to an outdoor deck.

9. 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 NZ$309
includes taxes & fees
4 Nov - 5 Nov
Cute Family Cabin at Lakeview by Sue
A small, single-story building with a porch and a fenced yard.

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

Grandma's Cabin at Stockton Lake, Stockton Missouri.
Stockton
9.6 out of 10, Exceptional, (61 reviews)
"Cute little cabin."
United States
Tania
The price is NZ$248
includes taxes & fees
4 Nov - 5 Nov
Grandma's Cabin at Stockton Lake, Stockton Missouri.
A small wooden cabin with a green roof, a white door, and a window. There is a picnic table and a barbecue grill outside.

11. Cabin 10 - Reel and Trigger

Cabin 10 - Reel and Trigger
Tom Township
9.0 out of 10, Wonderful, (2 reviews)
"We had family camping at the state park for the long weekend and wanted to stay close by. The cabin was perfect. We had time to visit easily and also an air conditioned place to sleep in. It also is dog friendly so we were able to bring the dogs. Getting a dog sitter on a long weekend is difficult. "
United States
Audrey B.
The price is NZ$266
includes taxes & fees
17 Nov - 18 Nov
Cabin 10 - Reel and Trigger
A two-story wooden house with a covered porch and a flagpole.

12. Truman Lake Retreat: Relax and Unwind

Truman Lake Retreat: Relax and Unwind
Clinton
10.0 out of 10, Exceptional, (15 reviews)
"A very nice place to stay that was conveniently located to where we spent most of our time."
United States
Jason S.
The price is NZ$866
includes taxes & fees
25 Nov - 26 Nov
Truman Lake Retreat: Relax and Unwind
A rustic building labeled 'Wagoner Grocery' with a red and gray exterior, a wooden porch, and a sign for 'Grandpa's Cabin.'

13. Grandpa's Cabin

Grandpa's Cabin
Stockton
9.6 out of 10, Exceptional, (4 reviews)
"It has everything you need for a good stay. While small, it is clean and easy."
United States
Mary A.
The price is NZ$239
includes taxes & fees
4 Dec - 5 Dec
Grandpa's Cabin
A log cabin interior with a fireplace, wooden walls, a sofa, and a staircase.

14. Secluded Lake Cabin w/ Hiking Trails & Firepit

Secluded Lake Cabin w/ Hiking Trails & Firepit
Deepwater
9.4 out of 10, Exceptional, (34 reviews)
"It was great and world stay there again!"
United States
Molly B.
The price is NZ$730
includes taxes & fees
9 Nov - 10 Nov
Secluded Lake Cabin w/ Hiking Trails & Firepit
A wooden deck with outdoor furniture, a sliding glass door, and a clear view of the backyard.

15. 2 Mi to Stockton Lake: Family Home w/ Grill

2 Mi to Stockton Lake: Family Home w/ Grill
Stockton
10.0 out of 10, Exceptional, (4 reviews)
"The home was very clean, comfortable and nicely decorated. The host was easy to communicate with and very kind. The kitchen was well equipped and there were even snacks left for us. It was perfect for our stay."
United States
Angela T.
The price is NZ$417
includes taxes & fees
5 Nov - 6 Nov
2 Mi to Stockton Lake: Family Home w/ Grill
A two-story wooden house with a covered porch and a flagpole.

16. Truman Lake Retreat: Relax and Unwind

Truman Lake Retreat: Relax and Unwind
3.0 star property
Clinton
The price is NZ$915
includes taxes & fees
25 Nov - 26 Nov
Truman Lake Retreat: Relax and Unwind
A laundry room with a washing machine, dryer, and ironing board. A television is mounted on the wall, and a remote control is on the table.

17. Cozy Home w/ Doggy Fence

Cozy Home w/ Doggy Fence
Warsaw
9.0 out of 10, Wonderful, (75 reviews)
"All the comforts of home, very reasonably priced."
United States
Greg
The price is NZ$323
includes taxes & fees
9 Nov - 10 Nov
Cozy Home w/ Doggy Fence
A modern kitchen with a central island, bar stools, and a 'Please Clean Up After Yourself' sign.

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

Charming 3-bedroom cabin in delightful Stockton with WiFi, AC,
Stockton, MO 65785
8.6 out of 10, Excellent, (50 reviews)
"Great location wonderful hosts"
United States
Allison B.
The price is NZ$287
includes taxes & fees
9 Nov - 10 Nov
Charming 3-bedroom cabin in delightful Stockton with WiFi, AC,
A covered outdoor dining area with a table, chairs, a ceiling fan, and a view of the surrounding landscape.

19. Family Fave_On Truman Lake |4 BR|Fire Pit+Arcade

Family Fave_On Truman Lake |4 BR|Fire Pit+Arcade
Warsaw
9.8 out of 10, Exceptional, (10 reviews)
"Good amount of space for us during our stay.We were less than 10 minutes from Truman State Park and Marina and 15 minutes to town.Well stocked kitchen to include spices, utensils, and other cooking items."
United States
Dave W.
Family Fave_On Truman Lake |4 BR|Fire Pit+Arcade
A modern living room with a sectional sofa, a small ottoman, a staircase, and a kitchen area with wooden cabinets and appliances.

20. Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw

Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw
Warsaw
10.0 out of 10, Exceptional, (4 reviews)
"Very nice little place. Perfect place to stay for a fishing trip on Truman Lake. "
United States
Caleb T.
The price is NZ$524
includes taxes & fees
8 Nov - 9 Nov
Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw
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

10/10 Excellent
"We drove right past it at first. We we’re very impressed with how they remodeled this old motel. It was beautiful actually. Well thought out. Beds were very comfortable. Good lighting in the rooms. Beautiful parking lot and you pulled right up to your room. Handy!! Went to grab a sandwich at 8:45. When I got back, the parking lot was full at 9:15. A sink in the bathroom and outside of the bathroom. Pretty granite tops. Will stay again!! Thanks guys!"
Robin 1-night trip
Posted 9 hours 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, 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$205 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.