Osceola Vacations from $870

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Your Osceola Vacation

Choose a Osceola vacation package and concentrate on what matters — having some fun. There's no more planning hassles, just a lot more time to uncover the best parts of this lively city, such as its rich history and friendly locals. A trip to Osceola wouldn't be complete without checking out a few top attractions, like Osceola Cheese. Your dream Osceola vacation is a few clicks away. Browse hotels, flights and more on Expedia for a getaway that's tailored to suit your travel style.

The Latest Osceola vacation packages

Price found within the past 48 hours. Click for updated prices.
Amazing Lake Views With Pool, Loft, & Balcony

Amazing Lake Views With Pool, Loft, & Balcony

2 out of 5
Price was $891, price is now $870 per person
$870
per person
Dec 24 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Versailles (VRS)
No reviews
Amazing Lake Views Within State Park - Gated Pool

Amazing Lake Views Within State Park - Gated Pool

2 out of 5
Price was $958, price is now $930 per person
$930
per person
Dec 24 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Versailles (VRS)
No reviews
Amazing Views From Balcony, Loft & Gated Pool

Amazing Views From Balcony, Loft & Gated Pool

2 out of 5
Price was $959, price is now $932 per person
$932
per person
Dec 24 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Versailles (VRS)
No reviews
Penthouse Living In The Heart of the State Park

Penthouse Living In The Heart of the State Park

2 out of 5
Price was $973, price is now $945 per person
$945
per person
Dec 24 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Versailles (VRS)
No reviews
Lakefront Escape, Sunrise Views, Boat Slip & Community Dock Access

Lakefront Escape, Sunrise Views, Boat Slip & Community Dock Access

2 out of 5
Price was $941, price is now $919 per person
$919
per person
Dec 24 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Versailles (VRS)
No reviews
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Discover the most popular places to visit in Osceola

Osceola Cheese

Enjoy an outing to Osceola Cheese during your stay in Osceola.

Osceola Cheese

Osceola Hotel Deals

Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy

2 out of 5
11750 NE 230 Rd, Osceola, MO
$164 nightly
The price is $172 total per night from Nov 18 to Nov 19
$172 total
Nov 18 - Nov 19
Total with taxes and fees
9.8/10 Exceptional! (29 reviews)
Good

Reviewed on Oct 26, 2025

Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy
Secluded Hunting & Fishing cabin in the Woods - Osceola, MO

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

Osceola
$188 nightly
The price is $195 total per night from Nov 23 to Nov 24
$195 total
Nov 23 - Nov 24
Total with taxes and fees
9.8/10 Exceptional! (20 reviews)
The property was great, perfect for a quiet relaxing weekend

Reviewed on Oct 30, 2025

Secluded Hunting & Fishing cabin in the Woods - Osceola, MO
Historic Commercial Hotel (Est.1868) Sally Rand Suite

Historic Commercial Hotel (Est.1868) Sally Rand Suite

Osceola
$100 nightly
The price is $106 total per night from Nov 18 to Nov 19
$106 total
Nov 18 - Nov 19
Total with taxes and fees
9.6/10 Exceptional! (16 reviews)
We stayed in the Sally Rand room. The room and bed were comfortable and within walking distance to an awesome coffee shop (The Leaky Roof?) and a nice little stroll down by the river where we saw eagles in the trees. This was a unique place to stay for us to break up a long drive. The host was friendly ...

Reviewed on Oct 27, 2025

Historic Commercial Hotel (Est.1868) Sally Rand Suite
See all 235 properties in Osceola
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.

Find the Best Osceola Vacation Packages

Osceola Essential Information

Language
English
Currency
U.S dollars
Population
920

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Frequently asked questions

How much does an Osceola vacation package cost?
You'll find cheap prices from $870 on Expedia for your Osceola break. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Osceola costs.
What are the cheapest months to go to Osceola?
If you're looking to book a cheap Osceola vacation package, consider visiting in December, January and February. You're likely to find better prices on airfares and hotels during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Osceola?
With a well-organized itinerary, you can easily visit the top Osceola sights in a few days. But if you want to discover hidden spots or go on day trips, consider booking your Osceola vacation for longer.
How to find the best Osceola package deals?
Start your search for an Osceola package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Osceola package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Osceola getaway off to a flying start.
Is it cheaper to book an Osceola vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Osceola vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Osceola?
If you've got your Osceola travel dates finalized, book as early as you can to snap up some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for impromptu escapes.
Does Expedia offer Book Now, Pay Later Osceola vacation packages?
Jet off on your dream getaway to Osceola with our Book Now, Pay Later vacations. No need to save up or hold off until your next payday — we've joined forces with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no hidden or late payment fees, you can easily budget for your trip and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.