Title: Book the Best Hotels with POOL in Osceola in 2026 | Expedia.ca [Hotels in Osceola](https://expedia.ca/Osceola-Hotels.d553248634983526126.Travel-Guide-Hotels)[Vacation Rentals in Osceola](https://expedia.ca/Osceola-Vacation-Rentals.d553248634983526126.Travel-Guide-VacationRentals)[Osceola Car Rentals](https://expedia.ca/Car-Rentals-In-Osceola.d553248634983526126.Car-Rental-Guide)[Osceola Vacation Packages](https://expedia.ca/Osceola.d553248634983526126.Destination-Travel-Guides) ![Beauty on the backroads.](https://images.trvl-media.com/place/553248634983526126/5c79f899-9d3c-41ad-9472-5f8dc4af0d27.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Kelly Lasswell ![](https://images.trvl-media.com/place/553248634983526126/5c79f899-9d3c-41ad-9472-5f8dc4af0d27.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Osceola Hotels with a Pool Tonight [Jan 17 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248634983526126&startDate=2026-01-17&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 18 - Jan 19](https://www.expedia.ca/Hotel-Search?regionId=553248634983526126&startDate=2026-01-18&endDate=2026-01-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248634983526126&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248634983526126&startDate=2026-01-30&endDate=2026-02-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Osceola hotels with a pool ![Exterior](https://images.trvl-media.com/lodging/60000000/59050000/59043500/59043439/a101a5ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/60000000/59050000/59043500/59043439/fb3e3d60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59050000/59043500/59043439/3ea04ed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/59050000/59043500/59043439/2cb7bc36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Commercial Hotel (Est.1868) Sally Rand Suite [](https://www.expedia.ca/Osceola-Hotels-Historic-Commercial-Hotel-Sally-Rand-Suite.h59043439.Hotel-Information) Osceola 9.6/10 Exceptional (17 reviews) "A unique hotel with lots of history- a fun place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter CA $111 CA $147 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Osceola-Hotels-Historic-Commercial-Hotel-Sally-Rand-Suite.h59043439.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/60000000/59180000/59177800/59177782/03d0015d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59180000/59177800/59177782/9ebf8a8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59180000/59177800/59177782/1149d3d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59180000/59177800/59177782/fd5b4781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Commercial Hotel(Est. 1868)Tom Mix Suite [](https://www.expedia.ca/Osceola-Hotels-Historic-Commercial-Hoteltom-Mix-Suite.h59177782.Hotel-Information) Osceola 9.8/10 Exceptional (17 reviews) "Great place. We loved the historical signs and display cases with artifacts around the hotel. The celebration in the town square was a nice bonus. Very quiet and quaint. I wish we'd have had more time to do a little fishing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) B P. CA $119 CA $155 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Osceola-Hotels-Historic-Commercial-Hoteltom-Mix-Suite.h59177782.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1330000/1328700/1328698/7967f13d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1330000/1328700/1328698/57a2f2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1330000/1328700/1328698/56b61525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, soundproofing, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1330000/1328700/1328698/83af4b4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parkfield Inn [](https://www.expedia.ca/Clinton-Hotels-Parkfield-Inn.h1328698.Hotel-Information) Clinton 9.2/10 Wonderful (977 reviews) "Great place to stay. We will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $134 CA $151 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Clinton-Hotels-Parkfield-Inn.h1328698.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/70000/67500/67453/608cda4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/70000/67500/67453/be83e179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/1000000/70000/67500/67453/ed683b43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/67500/67453/2066b075.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westbridge Inn and Suites [](https://www.expedia.ca/Clinton-Hotels-Westbridge-Inn-And-Suites.h67453.Hotel-Information) Clinton 8.0/10 Very good (730 reviews) "Staff was great! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela CA $106 CA $125 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Clinton-Hotels-Westbridge-Inn-And-Suites.h67453.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723214/ec8f1bd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room | Bathroom sink](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723214/96802420.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723214/f8c7e482.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room | Private kitchenette](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723214/0d4adac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parkfield Inn [](https://www.expedia.ca/Clinton-Hotels-Parkfield-Inn.h1723214.Hotel-Information) Warsaw 9.4/10 Exceptional (597 reviews) "Close to town, places to eat, lake to fish. All around clean, good breakfast and friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary CA $149 CA $167 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Clinton-Hotels-Parkfield-Inn.h1723214.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/28000000/27600000/27597500/27597474/1a9e2fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/28000000/27600000/27597500/27597474/059b8066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room 2 Beds Nonsmoking Upper Level](https://images.trvl-media.com/lodging/28000000/27600000/27597500/27597474/227ad2f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, soundproofing, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/28000000/27600000/27597500/27597474/46d2ae02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakes Inn [](https://www.expedia.ca/Clinton-Hotels-Lakes-Inn.h27597474.Hotel-Information) Warsaw 8.0/10 Very good (354 reviews) "It was a great stay. Better than I could have imagined. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $110 CA $124 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Clinton-Hotels-Lakes-Inn.h27597474.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/104000000/103250000/103244300/103244252/ea60bc29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Cabin, Resort View | Private kitchen](https://images.trvl-media.com/lodging/104000000/103250000/103244300/103244252/7cce3d59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fishing](https://images.trvl-media.com/lodging/104000000/103250000/103244300/103244252/33ed06b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Cabin, Resort View | Terrace/patio](https://images.trvl-media.com/lodging/104000000/103250000/103244300/103244252/79178aa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hickory Hollow Resort [](https://www.expedia.ca/Clinton-Hotels-Hickory-Hollow-Resort.h103244252.Hotel-Information) Clinton 8.4/10 Very good (13 reviews) "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](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry CA $124 CA $146 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Clinton-Hotels-Hickory-Hollow-Resort.h103244252.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/106000000/105610000/105609400/105609346/c9c62eaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/106000000/105610000/105609400/105609346/e823320a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105610000/105609400/105609346/4081d30e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105610000/105609400/105609346/85d80305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil Wooded Retreat Overlooking Truman Lake only 2 minutes from Warsaw, MO [](https://www.expedia.ca/Warsaw-Hotels-Tranquil-Wooded-Retreat-Overlooking-Truman-Lake-Only-2-Minutes-From-Warsaw.h105609346.Hotel-Information) Warsaw 10/10 Exceptional (8 reviews) "Perfect getaway in the woods. Very clean. Lovely accommodations." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin R. CA $356 CA $871 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Warsaw-Hotels-Tranquil-Wooded-Retreat-Overlooking-Truman-Lake-Only-2-Minutes-From-Warsaw.h105609346.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2026-01-31&endDate=2026-02-01®ionId=553248634983526126&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Osceola Hotel Reviews ![Parkfield Inn](https://images.trvl-media.com/lodging/2000000/1330000/1328700/1328698/a54e6ce3_y.jpg) ### Parkfield Inn 10/10 Excellent "The room was kept very clean each day. The hotel must have been recently renovated, as everything seemed new." [](https://expedia.ca/Clinton-Hotels-Parkfield-Inn.h1328698.Hotel-Information) ![Westbridge Inn and Suites](https://images.trvl-media.com/lodging/1000000/70000/67500/67453/917a0904_y.jpg) ### Westbridge Inn and Suites 10/10 Excellent "Everything, it was very nice place and very clean" [](https://expedia.ca/Clinton-Hotels-Westbridge-Inn-And-Suites.h67453.Hotel-Information) ![Parkfield Inn](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723214/0d4adac6_y.jpg) ### Parkfield Inn 10/10 Excellent "Friendly, helpful staff, clean facilities, nice amenities and convenient location. Thank you!" [](https://expedia.ca/Clinton-Hotels-Parkfield-Inn.h1723214.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Osceola? ### What is there to see and do in Osceola? ### When is the best time to book a hotel with a pool in Osceola? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Cabin Rentals in Appleton City ](https://www.expedia.ca/Appleton-City-Cabins.d553248634983571988-aaCabins.Travel-Guide-Accommodation) - [Appleton City Hotels ](https://www.expedia.ca/Appleton-City-Hotels.d553248634983571988.Travel-Guide-Hotels) - [Pet-Friendly Hotels in Bolivar ](https://www.expedia.ca/Bolivar-Hotels-Pet-Friendly-Hotel.0-0-d6763-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [B&B in Cedar County ](https://www.expedia.ca/Cedar-County-Bed-And-Breakfast.d553248635083916800-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Aparthotels in Clinton ](https://www.expedia.ca/Clinton-Apart-Hotels.d7500-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Clinton ](https://www.expedia.ca/Clinton-Bed-And-Breakfast.d7500-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Clinton ](https://www.expedia.ca/Clinton-Guest-Houses.d7500-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Clinton ](https://www.expedia.ca/Clinton-Hotels-Cheap-Hotels.0-0-d7500-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Clinton ](https://www.expedia.ca/Clinton-Hotels-Hotels-With-Indoor-Pool.0-0-d7500-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Clinton ](https://www.expedia.ca/Clinton-Hotels-Luxury-Hotel.0-0-d7500-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Clinton ](https://www.expedia.ca/Clinton-Hotels-Pet-Friendly-Hotel.0-0-d7500-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Clinton Hotels ](https://www.expedia.ca/Clinton-Hotels.d7500.Travel-Guide-Hotels) - [Lodges in Clinton ](https://www.expedia.ca/Clinton-Lodges.d7500-aaLodges.Travel-Guide-Accommodation) - [Hotels with Balconies in Missouri ](https://www.expedia.ca/Destinations-In-Missouri-Hotels-With-Balconies.0-0-d227-tHotelswithBalconies.Hotel-Filter-Destinations) - [Aparthotels in El Dorado Springs ](https://www.expedia.ca/El-Dorado-Springs-Apart-Hotels.d6126783-aaApartHotels.Travel-Guide-Accommodation) - [El Dorado Springs Hotels ](https://www.expedia.ca/El-Dorado-Springs-Hotels.d6126783.Travel-Guide-Hotels) - [Galmey Hotels ](https://www.expedia.ca/Galmey-Hotels.d6351834.Travel-Guide-Hotels) - [Lodges in Galmey ](https://www.expedia.ca/Galmey-Lodges.d6351834-aaLodges.Travel-Guide-Accommodation) - [Hotels near Harry S. 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