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Osceola Holiday 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 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
9.8 out of 10, Exceptional, (63 reviews)
"They are pet friendly and great spot for a get away"
United States
Safa
The price is AU$187
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 AU$217
includes taxes & fees
9 Oct - 10 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 AU$299
includes taxes & fees
9 Oct - 10 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 AU$340
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 AU$336
includes taxes & fees
4 Oct - 5 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 AU$336
includes taxes & fees
4 Oct - 5 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 AU$151
includes taxes & fees
14 Oct - 15 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 AU$198
includes taxes & fees
9 Oct - 10 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 AU$254
includes taxes & fees
4 Oct - 5 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 AU$209
includes taxes & fees
3 Oct - 4 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 AU$276
includes taxes & fees
4 Oct - 5 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 AU$612
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 AU$231
includes taxes & fees
4 Oct - 5 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 AU$355
includes taxes & fees
3 Oct - 4 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 AU$281
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 AU$350
includes taxes & fees
6 Oct - 7 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 AU$209
includes taxes & fees
3 Oct - 4 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 AU$440
includes taxes & fees
4 Oct - 5 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 AU$425
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.
The price is AU$995
includes taxes & fees
4 Oct - 5 Oct
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

GRANDMA'S GET-A-WAY (Water Front property ) WIFI. Private covered one bay dock.

GRANDMA'S GET-A-WAY (Water Front property ) WIFI. Private covered one bay dock.

10/10 Excellent
"Other travelers should be aware of steps down to dock. Everything you need is there. Enjoyable"
Roland D. 3-night trip
Posted 23 hours ago
GRANDMA'S GET-A-WAY (Water Front property ) WIFI. Private covered one bay dock.

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 favourite 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 depend 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 AU$151 per night. Entering your travel dates in the search wizard might find you 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.