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Osceola Vacation Rentals

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Vacation Rentals in Osceola

Fridge, microwave, oven, stovetop
Secluded Hunting & Fishing cabin in the Woods - Osceola, MO

Cabin in Osceola

9.8 out of 10, Exceptional, (20)
"Great secluded Cabin with all ammenities you need, very clean and well kept would definetly recommend!"
United States
william
$188 nightly
The price is $195
Dec 7 - Dec 8
Total with taxes and fees
Secluded Hunting & Fishing cabin in the Woods - Osceola, MO
Fridge, microwave, oven, stovetop
The Chestnut on the Square Historic Loft A

Apartment in Osceola

10.0 out of 10, Exceptional, (38)
"Very nice place to stay with plenty of room. Really easy to get to and beautiful place."
United States
Craig S.
$162 nightly
The price is $170
Dec 10 - Dec 11
Total with taxes and fees
The Chestnut on the Square Historic Loft A
Fridge, microwave, oven, stovetop
Peaceful Lakefront Cabin

Cabin in Lincoln

9.8 out of 10, Exceptional, (6)
"Such a wonder stay, at a gorgeous, cozy home, with excellent property managers. Can’t rave enough about our experience! We even extended our stay by an additional day, because we loved it so much. "
United States
Jordan N.
Peaceful Lakefront Cabin
Terrace/patio
Lake Cottage Getaway at Pomme De Terre Lake

Vacation Home in Hermitage

10.0 out of 10, Exceptional, (83)
"Amazing and peaceful "
United States
Casey M.
Lake Cottage Getaway at Pomme De Terre Lake
Fridge, microwave, oven, stovetop
Charming 3-bedroom cabin in delightful Stockton with WiFi, AC,

Cabin in Stockton, MO 65785

2.0 star property
9.2 out of 10, Wonderful, (28)
"Overall we really liked the property."
United States
Jessica W.
$112 nightly
The price is $112
Dec 8 - Dec 9
Total with taxes and fees
Charming 3-bedroom cabin in delightful Stockton with WiFi, AC,
Property grounds
Wolf Cub Cab of Pomme de Terre

Cabin in Bolivar

9.4 out of 10, Exceptional, (111)
"We had a great time staying at this cabin. "
United States
Michelle L.
Wolf Cub Cab of Pomme de Terre
Exterior
Grandma's Cabin at Stockton Lake, Stockton Missouri.

Cabin in Stockton

9.8 out of 10, Exceptional, (54)
"We enjoyed our stay. It was peaceful and quiet. "
United States
Melanie
$127 nightly
The price is $127
Dec 4 - Dec 5
Total with taxes and fees
Grandma's Cabin at Stockton Lake, Stockton Missouri.
Microwave, oven, stovetop
Charming 2-bedroom house with WiFi and AC in Warsaw close to launch ramps

Vacation Home in Warsaw

10.0 out of 10, Exceptional, (3)
"The house was very clean! "
United States
brandon a.
$245 nightly
The price is $250
Dec 4 - Dec 5
Total with taxes and fees
Charming 2-bedroom house with WiFi and AC in Warsaw close to launch ramps
Dining
2 bedroom cabin close to Pomme de Terre Lake

Cabin in Flemington

9.2 out of 10, Wonderful, (20)
"Nice place easy process"
United States
Curtis T.
2 bedroom cabin close to Pomme de Terre Lake
Smart TV, fireplace
Lake house with a view! Overlooks Warsaw and Lake of the Ozarks, Sleeps 4

Vacation Home in Warsaw

10.0 out of 10, Exceptional, (50)
"Really loved the experience and great local place to stay with family"
United States
Bre H.
Lake house with a view! Overlooks Warsaw and Lake of the Ozarks, Sleeps 4
Terrace/patio
Whole house on a quiet cove, Lake of the Ozarks, Family owned and operated.

Vacation Home in Warsaw

10.0 out of 10, Exceptional, (69)
"Great house to accommodate a large group. It was a wonderful stay on the water."
United States
Michelle B.
Whole house on a quiet cove, Lake of the Ozarks, Family owned and operated.
Property grounds
Lakefront Home/Amazing Lake View/Pomme Paradise #2

Vacation Home in Pittsburg

9.6 out of 10, Exceptional, (16)
"Lovely place!"
United States
Janet W.
Lakefront Home/Amazing Lake View/Pomme Paradise #2
Property grounds
Ozark Family Getaway in beautiful Warsaw.

Vacation Home in Warsaw

9.6 out of 10, Exceptional, (33)
"This was our second time staying here and it was just as great as the first! Such a great house and the host is so easy to work with! "
United States
Kyndal B.
Ozark Family Getaway in beautiful Warsaw.
Fridge, microwave, oven, stovetop
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown

Vacation Home in Clinton

9.8 out of 10, Exceptional, (19)
"Enjoyed our stay! Neat little property. Met all our needs. Kitchen had all the supplies. Communication great. Appreciate the locked shed for our bikes. Will stay again. "
United States
Joseph
$159 nightly
The price is $159
Dec 4 - Dec 5
Total with taxes and fees
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown
Property grounds
Lazy H Cabin Rental located in a friendly little community

Cabin in Warsaw

9.4 out of 10, Exceptional, (10)
"We had a great experience, the owner was very nice the property was very clean nice quiet and peaceful.I would definitely recommend to anybody looking to get away definitely will be going back."
United States
Thomas L.
Lazy H Cabin Rental located in a friendly little community
Terrace/patio
Water front Lake of the Ozarks Studio Apartment

Apartment in Warsaw

9.8 out of 10, Exceptional, (33)
"Stay for a few days, Very quite place, clean and host was friendly."
United States
How to by V
Water front Lake of the Ozarks Studio Apartment
Living area
Cedar Ridge, 3BR 2 Bath Cabin on Truman Lake

Vacation Home in Deepwater

9.2 out of 10, Wonderful, (28)
"This place was lovely, clean, and had wonderful views!"
United States
Terri R.
Cedar Ridge, 3BR 2 Bath Cabin on Truman Lake
Terrace/patio
Large lake home 1/2 mile from boat ramp and courtesy dock on Stockton Lake

Vacation Home in Stockton

10.0 out of 10, Exceptional, (54)
"Great place for a family. Lots of room and well equipped. Short walk to the lake or drive to the State Park. "
United States
Matt R.
Large lake home 1/2 mile from boat ramp and courtesy dock on Stockton Lake
Exterior
2-bedroom vacation home just 8 minutes from Stockton Lake

Vacation Home in Humansville

10.0 out of 10, Exceptional, (12)
"An outstanding place to stay, and such lovely people to host! Seriously, they were extremely accommodating and so amazing "
United States
James K.
$128 nightly
The price is $128
Dec 4 - Dec 5
Total with taxes and fees
2-bedroom vacation home just 8 minutes from Stockton Lake
Basic Cabin, Resort View | Private kitchen
Hickory Hollow Resort

Cabin in Clinton

2.0 star property
8.4 out of 10, Very Good, (13)
"Our cabin was clean, comfortable and affordable. The check-in was effortless and we had no issues with the stay. I would recommend the place to friends and family traveling through the area."
United States
Terry
$99 nightly
The price is $105
Jan 2 - Jan 3, 2026
Total with taxes and fees
Hickory Hollow Resort
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
"Clean and comfortable,courteous staff"
Valda 1-night trip
Posted 7 days ago
Westbridge Inn and Suites

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Osceola in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $112 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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?

Lake Cottage Getaway at Pomme De Terre Lake: This vacation home rental outside of Osceola is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Osceola?

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