Osceola Holiday Rentals : Search Short-Term Rentals

Q: What are some of the best holiday rentals that Osceola has to offer?

Rm 1 - Waterfront Double Queen / 1st floor : This holiday home rental outside of Osceola has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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Holiday Rentals in Osceola

Stunning staircase with a patterned carpet and a bench on the landing, surrounded by framed pictures and a historic sign.

"The history and atmosphere was so unique. Our room was quiet and very peaceful. We would stay there again."

includes taxes & fees

20 Jul - 21 Jul

Enjoy a serene riverside retreat with a covered patio and scenic views.

"Nice people. Very quiet and close fishing. "

includes taxes & fees

23 Jul - 24 Jul

Enjoy outdoor cooking on the covered porch, surrounded by mature trees in a natural setting.

"Great property"

includes taxes & fees

19 Jul - 20 Jul

Enjoy a meal with a view at this scenic picnic area, featuring a pavilion with picnic tables and a grill.

"Had a great time!! Checkin couldn’t have been easier, was clean and was able to find anything we needed as far as frying up some fish:) lake must be low as the boat ramp was fairly dried up. Great place to take the dogs and get away for a couple days and do some fishing."

includes taxes & fees

27 Jul - 28 Jul

Modern kitchen with white cabinetry, stainless steel appliances, and a black countertop.

"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. "

includes taxes & fees

18 Aug - 19 Aug

Enjoy cooking in this kitchen with a central island, sink, and bar stools for ample workspace and seating.

"Had a great time!"

includes taxes & fees

25 Jul - 26 Jul

Cozy retreat with a traditional lodge feel, featuring a wooden bench and a door leading to a separate room.

"The house was nice and clean, nice getaway."

includes taxes & fees

20 Jul - 21 Jul

Relax under the shaded pergola with a bench and chair, perfect for socializing or unwinding.

"The cabin was amazing everything you need issupplied it is wonderful and with a warm cozy feel "

includes taxes & fees

21 Jul - 22 Jul

"Very nice, very clean. Great location."

includes taxes & fees

21 Jul - 22 Jul

Enjoy dining or socializing in this sheltered patio area with tables and chairs.

"My children really enjoyed all of the animals. There was enough space for two families to spread out, which was wonderful. Although right on the highway, it was quiet and peaceful. Thank you!"

includes taxes & fees

15 Aug - 16 Aug

Enjoy cooking in this well-equipped kitchen with a central island, microwave, oven, and refrigerator.

"Liked long driveway and easy access. Clean comfy respectable place. Communication was great!! "

includes taxes & fees

21 Jul - 22 Jul

Enjoy cooking in this kitchen with dark green cabinetry, granite countertop, and stainless steel sink.

"Roomy and loved quiet neighborhood "

includes taxes & fees

30 Jul - 31 Jul

Relax in this spacious living room with a high ceiling, featuring a large sofa and armchair, a coffee table, and wooden paneling.

"Had 10 people in the house plenty of room will definitely be staying there again"

includes taxes & fees

20 Jul - 21 Jul

Effortlessly cook and entertain in this well-designed kitchen with a black countertop, ample storage, and oven.

"This was a beautiful place to stay and so easy to check in and out of!! Thankful there wasn't the normal check list of things we had to do before leaving the property!"

includes taxes & fees

22 Jul - 23 Jul

Enjoy cooking in this well-equipped kitchen with a large island, stainless steel appliances, and pendant lights.

"Such a perfect house for a family getaway. The kitchen is beautiful and has everything we needed. The hot tub was so relaxing. The beds were comfortable. Nice, quiet neighborhood, close to Sterrett Creek Marina. Wish we could have stayed longer!"

Relax on the patio surrounded by a pergola, a wooden table, and two chairs, with a fire feature and a view of the sky.

"Loved our stay here!! Just my husband and I for a getaway and feels so secluded, but so close to town or any boat ramp or the marina. Very clean, lots of things to make your stay comfy! Will be back for sure!"

includes taxes & fees

19 Jul - 20 Jul

Relax under the pergola, where a table and bench invite you to dine or unwind.

"Great little place to stay. We have stayed at these rentals for 2 years in a row for our anniversary. The hot tub is amazing and so clean and just what we needed to relax."

includes taxes & fees

22 Jul - 23 Jul

Enjoy a serene view of the river from this balcony.

"Very nice stay, awesome view and good fishing !! Super nice owners!"

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Top Osceola Hotel Reviews

Parkfield Inn

10/10 Excellent

"Clean. Friendly. Could use area for outdoor seating. "

Relax at Grandma’s house with a screened in porch overlooking a private lake!

10/10 Excellent

"The property and host were amazing! The location is a short drive from many amenities. I felt like I was in my home away from home. I would highly recommend this location. I often use VRBO, and, I was completely satisfied. If there was an emergency, we had help very close to us. You have to appreciate the small things as well as the big ones. My wife has a few pictures, I am not good at taking pictures so I only have a few of my dog. She loved the screened in porch and supervising the neighbor as he worked hard all day. She was pooped watching him. 5 out of 5!!!"

Whole house on a quiet cove, Lake of the Ozarks, Family owned and operated.

10/10 Excellent

"They really worked with us on some issues and we really appreciated that. Everything is so nice there and if you like to fish and do not have a boat - the dock is good. It's in a cove so there are no waves. We had our little family reunion there and everyone loved it there. We would love to do this again."

Find out more about Osceola

Everything you need to know about Osceola holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osceola holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osceola holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osceola holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osceola holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Osceola rentals

At Expedia, we put the best Osceola holiday 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 holiday.

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 holiday rental in Osceola?

Yes, there are holiday rentals in Osceola close to Osceola Cheese, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Osceola has to offer?

Rm 1 - Waterfront Double Queen / 1st floor: This holiday home rental outside of Osceola has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Osceola?

Truman Lake 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 holiday rentals like in Osceola?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osceola. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for family trips.

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Holiday Rentals in Osceola

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Holiday Rentals in Osceola

Historic Commercial Hotel(Est.1868) "Dam Room"

Rm 1 - Waterfront Double Queen / 1st floor

2-bedroom vacation home just 8 minutes from Stockton Lake

Cozy Home w/ Doggy Fence

Peaceful Lakefront Cabin

The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown

Cedar Lodge is quaint rustic lodge with modern amenities. Relaxing and warm!

Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw

Stockton Lake Getaway Less than 1/2 mi to Lake

Stockton Lakes’ Rustic Retreat - Cozy & Close

The Farmhouse at Truman Lake

Charming 2-bedroom house with WiFi and AC in Warsaw close to launch ramps

Hunters Paradise on The Lake. Cozy 2 bedroom house with large back yard

Lake House on Truman Lake

The Lodge - Large Rental

Modern and Spacious with game/movie room.

Brand New Home near Truman Lake with New Hot Tub, Access to Boat Ramp/Marina.

Minutes away from Stockton Lake

Jupiter at Starburst, a Private modern luxury vacation rental

Rm 2 -Waterfront Double Queen / 2nd floor

Top Osceola Hotel Reviews

Parkfield Inn

Relax at Grandma’s house with a screened in porch overlooking a private lake!

Parkfield Inn

Lakes Inn

Postcard Cabins Ozark Highlands

Westbridge Inn and Suites

Whole house on a quiet cove, Lake of the Ozarks, Family owned and operated.

Lake of the Ozarks Lake Front, 3 mi to Truman Lake, Three Bedrm Lake Home.

The BarnwooD Inn

Find out more about Osceola

Frequently asked questions