Osceola Vacation Rentals from CA $145: Short-Term Rentals for 2026

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Our top choices for Osceola vacation rentals

A compact kitchen with white cabinets, a microwave, and a refrigerator.

1. Chestnut on the square, unit B

Osceola

Evan B.

CA $204 total

includes taxes & fees

Sep 18 - Sep 19

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.

2. The Chestnut on the Square Historic Loft A

Osceola

Brandon J.

CA $279 total

includes taxes & fees

Sep 21 - Sep 22

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

Osceola

Safa

CA $192 total

includes taxes & fees

Oct 7 - Oct 8

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

Osceola

Hailee W.

CA $271 total

includes taxes & fees

Sep 13 - Sep 14

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.

Deepwater

Cynthia M.

CA $314 total

includes taxes & fees

Sep 21 - Sep 22

A park with a playground, a bench, a lamppost, and a view of a lake.

6. Cozy Home w/ Doggy Fence

Warsaw

Todd C.

CA $248 total

includes taxes & fees

Sep 13 - Sep 14

A small, single-story building with a porch and a fenced yard.

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

Stockton

Jessica B.

CA $197 total

includes taxes & fees

Oct 6 - Oct 7

A row of cabins with wooden decks and stairs leading to the entrance.

8. Hickory Hollow Resort

Clinton

Sam

CA $145 total

includes taxes & fees

Sep 9 - Sep 10

A log cabin interior with a fireplace, wooden walls, a sofa, and a staircase.

9. Secluded Lake Cabin w/ Hiking Trails & Firepit

Deepwater

Mark O.

CA $601 total

includes taxes & fees

Sep 14 - Sep 15

A rustic building labeled 'Wagoner Grocery' with a red and gray exterior, a wooden porch, and a sign for 'Grandpa's Cabin.'

10. Grandpa's Cabin

Stockton

Cedric J.

CA $197 total

includes taxes & fees

Oct 7 - Oct 8

A wooden interior with a large barrel, a table with a vase, and a view of a lake through glass doors.

11. Romantic Country Cabin at Lakeview by Sue

Appleton City

Anna G.

CA $240 total

includes taxes & fees

Sep 13 - Sep 14

A wooden interior with a sliding glass door leading to an outdoor deck.

12. Cute Family Cabin at Lakeview by Sue

Appleton City

Lee C.

CA $260 total

includes taxes & fees

Sep 13 - Sep 14

A covered outdoor seating area with a red sofa and a table, overlooking a scenic view of a lake and forest.

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

Warsaw

Chris H.

CA $375 total

includes taxes & fees

Sep 27 - Sep 28

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

Stockton

CA $336 total

includes taxes & fees

Oct 1 - Oct 2

A modern kitchen with a central island, bar stools, and a 'Please Clean Up After Yourself' sign.

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

Stockton, MO 65785

Allison B.

CA $234 total

includes taxes & fees

Oct 7 - Oct 8

A kitchen with wooden cabinets, a bar area with stools, a wine rack, and a coffee station.

16. Large Family Cabin at Lakeview by Sue

Appleton City

Allie M.

CA $508 total

includes taxes & fees

Sep 10 - Sep 11

17. 2 Mi to Stockton Lake: Family Home w/ Grill

Stockton

"We arrived at the house after I traveled all day to be greeted by the cleanest and most comfortable property I think I’ve ever stayed in. The atmosphere was warm, cozy, inviting and safe. The location was close to everything I needed. The owners are very friendly and easily accessible and put in effort to make sure my stay was as pleasant as possible. If I ever need to stay in Stockton again, I will check to see if this property is available or reschedule a trip around this property being...

Carmelita

CA $339 total

includes taxes & fees

Oct 1 - Oct 2

A compact kitchen with wooden cabinets, a white refrigerator, a stove, and a trash bin.

18. Cabin 2 - Reel and Trigger

Tom Township

CA $218 total

includes taxes & fees

Sep 21 - Sep 22

A snow-covered landscape with several wooden houses, a barbecue grill, and a wooden bench.

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

Stockton

Tanya

CA $240 total

includes taxes & fees

Oct 4 - Oct 5

A spacious living room with a dark wood floor, a brown sectional sofa, a coffee table, and a ceiling fan.

20. Stockton Lakes’ Rustic Retreat - Cozy & Close

Stockton

Tom S.

CA $385 total

includes taxes & fees

Oct 8 - Oct 9

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Top Osceola Hotel Reviews

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

8/10 Good

"Nice place close to lake would recommend"

Westbridge Inn and Suites

8/10 Good

"The property was clean on the grounds and in the office. Rooms were clean and comfortable. The bathroom was clean and the water was hot. The television did not work. The room had a very strong smell of air freshener. It was a very strong smell - too strong really. There is an ice maker near the office. Staff was friendly. The rooms are reasonably well insulated and quiet. They use a monitor screen with a live attendant if you need something when the office is unmanned. I used it to check out. The staff works hard to keep the property up and they are friendly."

Ozarks Waterfront Home w/ Dock & Marina Access

10/10 Excellent

"We got to rest and had a beautiful view! It’s a quiet community there, if you’re looking for that it’s perfect. Only two places to eat close by so you may want to cook some at the cabin, which has everything you need. The town of Warsaw it’s about 16 miles away or so and plenty of options to shop or eat there. Robin, the host was awesome, very helpful guy and friendly. We got to meet his wife and family, very nice folks. The cabin is cozy and cute, beds comfy, large shower and a deck with a great view of the lake. Seen lots of deer around, and if you ride the golf cart in the evening as most folks do there, you can see them along the way, they’re not shy. We had our dog with us and she enjoyed swimming and being with us there. Perfect place to watch the stars, we got some beautiful shots of the Milky Way and saw some meteors too. If you’re looking for a quiet and relaxing get away this is your place. Thank you Robin and Brenda, we enjoyed it very much. Lilly, Dave and Bailey"

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

10/10 Excellent

"Grandma’s Getaway was a great place to getaway to relax and do some fishing. Very clean and Tammy the cleaning lady welcomed us and told us all about what was there for our stay. Went into Warsaw and did some antiquing. we will plan another stay there again. Thank you for sharing your hospitality and sharing your cabin."

Find out more about Osceola

Everything you need to know about Osceola vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osceola vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osceola vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osceola vacation rentals we have selected for you start as low as CA $145 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 vacation 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 vacation.

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 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.

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Check prices for these dates

Our top choices for Osceola vacation rentals

1. Chestnut on the square, unit B

2. The Chestnut on the Square Historic Loft A

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

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

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

6. Cozy Home w/ Doggy Fence

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

8. Hickory Hollow Resort

9. Secluded Lake Cabin w/ Hiking Trails & Firepit

10. Grandpa's Cabin

11. Romantic Country Cabin at Lakeview by Sue

12. Cute Family Cabin at Lakeview by Sue

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

14. 2 Mi to Stockton Lake: Family Home w/ Grill

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

16. Large Family Cabin at Lakeview by Sue

17. 2 Mi to Stockton Lake: Family Home w/ Grill

18. Cabin 2 - Reel and Trigger

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

20. Stockton Lakes’ Rustic Retreat - Cozy & Close

Find vacation rentals that suit your style

Top Osceola Hotel Reviews

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

Hickory Hollow Resort

Hidden Lake Resort

Westbridge Inn and Suites

Ozarks Waterfront Home w/ Dock & Marina Access

Lakes Inn

The BarnwooD Inn

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

Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy

Find out more about Osceola

Frequently asked questions

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