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Osceola Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Osceola vacation 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
9.8 out of 10, Exceptional, (63 reviews)
"They are pet friendly and great spot for a get away"
United States
Safa
The price is AED 309
AED 477 total
includes taxes & fees
2 Nov - 3 Nov
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, (31 reviews)
"Enjoyed our stay"
United States
tricia
The price is AED 404
AED 546 total
includes taxes & fees
10 Oct - 11 Oct
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, (48 reviews)
"Great place to stay "
United States
Brandon J.
The price is AED 551
AED 757 total
includes taxes & fees
10 Oct - 11 Oct
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
10.0 out of 10, Exceptional, (32 reviews)
"Such a nice, quiet, secluded cabin! "
United States
Hailee W.
The price is AED 430
AED 857 total
includes taxes & fees
5 Oct - 6 Oct
Secluded Hunting & Fishing cabin in the Woods - Osceola, MO
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, (50 reviews)
"Perfect getaway to relax. We enjoyed our trip and will be booking again!"
United States
Cynthia M.
The price is AED 455
AED 842 total
includes taxes & fees
5 Oct - 6 Oct
Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.
A snow-covered landscape with several wooden houses, a barbecue grill, and a wooden bench.

6. 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, (11 reviews)
"This was our 2nd year as a group We love this place. So clean so quiet a perfect spot"
United States
Tanya
The price is AED 389
AED 852 total
includes taxes & fees
5 Oct - 6 Oct
Water’s Edge Cabin: King & Queen Beds (Cabin 4)
A row of cabins with wooden decks and stairs leading to the entrance.

7. Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.4 out of 10, Very good, (25 reviews)
"Nice place to stay "
United States
Sam
The price is AED 327
AED 386 total
includes taxes & fees
8 Oct - 9 Oct
Hickory Hollow Resort
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, (24 reviews)
"Great Place to stay!"
United States
John F.
The price is AED 397
AED 496 total
includes taxes & fees
5 Oct - 6 Oct
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.

9. 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 AED 393
AED 638 total
includes taxes & fees
5 Oct - 6 Oct
Romantic Country 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 AED 312
AED 523 total
includes taxes & fees
5 Oct - 6 Oct
Grandma's Cabin at Stockton Lake, Stockton Missouri.
A wooden interior with a sliding glass door leading to an outdoor deck.

11. 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 AED 443
AED 694 total
includes taxes & fees
5 Oct - 6 Oct
Cute Family Cabin at Lakeview by Sue
A log cabin interior with a fireplace, wooden walls, a sofa, and a staircase.

12. Secluded Lake Cabin w/ Hiking Trails & Firepit

Secluded Lake Cabin w/ Hiking Trails & Firepit
Deepwater
9.4 out of 10, Exceptional, (33 reviews)
"Great views of Truman, awesome porch for all weather fun."
United States
Mark O.
The price is AED 981
AED 1,599 total
includes taxes & fees
5 Oct - 6 Oct
Secluded Lake Cabin w/ Hiking Trails & Firepit
A small wooden cabin with a green roof, a white door, and a window. There is a picnic table and a barbecue grill outside.

13. 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 AED 491
AED 579 total
includes taxes & fees
5 Oct - 6 Oct
Cabin 10 - Reel and Trigger
A wooden deck with outdoor furniture, a sliding glass door, and a clear view of the backyard.

14. 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 AED 364
AED 913 total
includes taxes & fees
5 Oct - 6 Oct
2 Mi to Stockton Lake: Family Home w/ Grill
A park with a playground, a bench, a lamppost, and a view of a lake.

15. Cozy Home w/ Doggy Fence

Cozy Home w/ Doggy Fence
Warsaw
9.0 out of 10, Wonderful, (72 reviews)
"All the comforts of home, very reasonably priced."
United States
Greg
The price is AED 311
AED 706 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Home w/ Doggy Fence
A wooden deck with outdoor furniture, a sliding glass door, and a clear view of the backyard.

16. 2 Mi to Stockton Lake: Family Home w/ Grill

2 Mi to Stockton Lake: Family Home w/ Grill
3.0 star property
Stockton
The price is AED 485
AED 894 total
includes taxes & fees
5 Oct - 6 Oct
2 Mi to Stockton Lake: Family Home w/ Grill
A rustic building labeled 'Wagoner Grocery' with a red and gray exterior, a wooden porch, and a sign for 'Grandpa's Cabin.'

17. 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 AED 312
AED 523 total
includes taxes & fees
5 Oct - 6 Oct
Grandpa's Cabin
A modern living room with a sectional sofa, a small ottoman, a staircase, and a kitchen area with wooden cabinets and appliances.

18. 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, (3 reviews)
"Very nice little place. Perfect place to stay for a fishing trip on Truman Lake. "
United States
Caleb T.
The price is AED 551
AED 1,140 total
includes taxes & fees
5 Oct - 6 Oct
Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw
A covered outdoor seating area with a red sofa and a table, overlooking a scenic view of a lake and forest.

19. Huge Lakeview|Unique Retreat on Truman Lake|Outdoor Firepit/180°IndoorViews

Huge Lakeview|Unique Retreat on Truman Lake|Outdoor Firepit/180°IndoorViews
Warsaw
10.0 out of 10, Exceptional, (90 reviews)
"Great place to stay! It was beautiful inside and out! "
United States
Chris H.
The price is AED 547
AED 1,085 total
includes taxes & fees
13 Oct - 14 Oct
Huge Lakeview|Unique Retreat on Truman Lake|Outdoor Firepit/180°IndoorViews
A covered outdoor dining area with a table, chairs, a ceiling fan, and a view of the surrounding landscape.

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

Family Fave_On Truman Lake |4 BR|Fire Pit+Arcade
Warsaw
10.0 out of 10, Exceptional, (9 reviews)
"Nice house! We enjoyed the area and this was a great house for our group of 8. Comfortable and we appointed."
United States
Becca B.
Family Fave_On Truman Lake |4 BR|Fire Pit+Arcade
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
"Not at all what I was expecting, more of a motel all down stairs out door style. Room was decent and id stop again if o needed"
Cassandra 1-night trip
Posted 1 day ago
Westbridge Inn and Suites

Frequently asked questions

Can I find a vacation rental in Osceola?

Yes, we give you a choice of vacation rentals in Osceola close to Osceola Cheese, or you can choose a secluded option if you'd like a relaxing place to stay.

What's the top vacation rental in Osceola?

GRANDMA'S GET-A-WAY (Water Front property ) WIFI. Private covered one bay dock.: This vacation home rental outside of Osceola is located on a lake and has a patio, a barbecue grill, 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 vacation rentals like in Osceola?

Vacation rentals are privately owned properties you can reserve for several days or longer in Osceola. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for families.