Photo by Kelly Lasswell

Osceola Hotels with Swimming Pool

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Osceola Hotels with Swimming Pools

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Osceola hotels with a pool

Indoor pool
Parkfield Inn

Parkfield Inn

Parkfield Inn
2.5 star property
Clinton
9.2 out of 10, Wonderful, (972)
"Great room and great service"
United States
Tiffany
The price is RM390
RM439 total
includes taxes & fees
31 Dec - 1 Jan 2026
Parkfield Inn
Outdoor pool
Westbridge Inn and Suites

Westbridge Inn and Suites

Westbridge Inn and Suites
2.0 star property
Clinton
8.0 out of 10, Very good, (725)
"Staff was great! "
United States
Angela
The price is RM310
RM365 total
includes taxes & fees
4 Jan - 5 Jan 2026
Westbridge Inn and Suites
Indoor pool
Parkfield Inn

Parkfield Inn

Parkfield Inn
2.0 star property
Warsaw
9.4 out of 10, Exceptional, (594)
"Close to town, places to eat, lake to fish. All around clean, good breakfast and friendly staff"
United States
Gary
The price is RM433
RM486 total
includes taxes & fees
31 Dec - 1 Jan 2026
Parkfield Inn
Seasonal outdoor pool
Lakes Inn

Lakes Inn

Lakes Inn
2.5 star property
Warsaw
8.0 out of 10, Very good, (354)
"It was a great stay. Better than I could have imagined. "
United States
Matthew
The price is RM324
RM363 total
includes taxes & fees
31 Dec - 1 Jan 2026
Lakes Inn
Seasonal outdoor pool
Hickory Hollow Resort

Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
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
The price is RM361
RM425 total
includes taxes & fees
30 Jan - 31 Jan 2026
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.
View all properties

Top Osceola Hotel Reviews

Parkfield Inn

Parkfield Inn

10/10 Excellent
"Yes it was"
Ruth 1-night trip
Posted 9 days ago
Parkfield Inn

Frequently asked questions

What are some accommodation options with pools in Osceola?
Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy: Features complimentary wireless Internet access, a communal pool and televisions. Westbridge Inn and Suites: Offers daily, an outdoor pool and free self parking. Parkfield Inn: Provides daily, an indoor pool and complimentary high-speed (wired) Internet access. Parkfield Inn: Features daily, an indoor pool and complimentary high-speed (wired) Internet access. Lakes Inn: Offers full, a seasonal outdoor pool and free self parking.
What is there to see and do in Osceola?
Make a point to visit attractions such as Harry S Truman Reservoir and Osceola Cheese. During your stay, visit sights such as Lilleys Island, Crowes Crossing Public Use Area and Gallinipper Creek State Wildlife Area.
When is the best time to book a hotel with a pool in Osceola?
You may want to consider accommodation that offers an outdoor pool if you plan to visit Osceola in the warmest months of July, August or June, when the average temperature is 24°C. Accommodation with an indoor pool may be what you want if you visit during the coldest months of January, February or December, when the average temp is 3°C.

Explore a world of travel with Expedia