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Osceola Vacation Rentals

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Check prices for these dates

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

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
9.6 out of 10, Exceptional, (79 reviews)
"Loved this location!! Will definitely revisit."
United States
Carmen
$124 nightly
The price is $130
Dec 6 - Dec 7
Total with taxes and fees
Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy
A row of cabins with wooden decks and stairs leading to the entrance.

2. 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
$108 nightly
The price is $116
Nov 14 - Nov 15
Total with taxes and fees
Hickory Hollow Resort
A two-story wooden house with a covered porch and a flagpole.

3. Truman Lake Retreat: Relax and Unwind

Truman Lake Retreat: Relax and Unwind
3.0 star property
Clinton
$469 nightly
The price is $514
Nov 25 - Nov 26
Total with taxes and fees
Truman Lake Retreat: Relax and Unwind
A wooden deck with outdoor furniture, a sliding glass door, and a clear view of the backyard.

4. 2 Mi to Stockton Lake: Family Home w/ Grill

2 Mi to Stockton Lake: Family Home w/ Grill
3.0 star property
Stockton
$224 nightly
The price is $243
Nov 8 - Nov 9
Total with taxes and fees
2 Mi to Stockton Lake: Family Home w/ Grill
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

View from property
Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy
Osceola

10/10 Excellent

Didn't like there wasn't a microwave, but other then that , it was the most wonderful place I have stayed, I will stay again.
United States
Melissa
Reviewed March 29, 2025
Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy

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 $115 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.

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.