Osceola Holiday Rentals

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Our top choices for Osceola holiday rentals

Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Ozark Highlands, Outdoor Collection by Marriott Bonvoy
2.0 star property
Osceola
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful all round !!! "
United States
Debra
The price is NZ$316
includes taxes & fees
11 May - 12 May
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
10.0 out of 10, Exceptional, (26 reviews)
"The property feels vet secluded and a lot of wild life."
United States
Anonymous traveller
The price is NZ$334
includes taxes & fees
6 May - 7 May
Secluded Hunting & Fishing cabin in the Woods - Osceola, MO

Chestnut on the square, unit B

Chestnut on the square, unit B
Osceola
10.0 out of 10, Exceptional, (27 reviews)
"Great place, very clean. "
United States
Evan B.
The price is NZ$252
includes taxes & fees
12 May - 13 May
Chestnut on the square, unit B

The Chestnut on the Square Historic Loft A

The Chestnut on the Square Historic Loft A
Osceola
10.0 out of 10, Exceptional, (43 reviews)
"Great place to stay "
United States
Brandon J.
The price is NZ$325
includes taxes & fees
12 May - 13 May
The Chestnut on the Square Historic Loft A

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

The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown
Clinton
9.8 out of 10, Exceptional, (28 reviews)
"Perfect place to stay during a weekend family visit!"
United States
Terry M.
The price is NZ$290
includes taxes & fees
7 May - 8 May
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown

2-bedroom vacation home just 8 minutes from Stockton Lake

2-bedroom vacation home just 8 minutes from Stockton Lake
Humansville
10.0 out of 10, Exceptional, (15 reviews)
"Nice place"
United States
Robert L.
The price is NZ$230
includes taxes & fees
7 May - 8 May
2-bedroom vacation home just 8 minutes from Stockton Lake

Romantic Country Cabin at Lakeview by Sue

Romantic Country Cabin at Lakeview by Sue
Appleton City
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay, so beautiful! "
United States
Anna G.
The price is NZ$296
includes taxes & fees
10 May - 11 May
Romantic Country Cabin at Lakeview by Sue

Grandma's Cabin at Stockton Lake, Stockton Missouri.

Grandma's Cabin at Stockton Lake, Stockton Missouri.
Stockton
9.8 out of 10, Exceptional, (55 reviews)
"We enjoyed our stay. It was peaceful and quiet. "
United States
Melanie
The price is NZ$243
includes taxes & fees
9 May - 10 May
Grandma's Cabin at Stockton Lake, Stockton Missouri.

2 Mi to Stockton Lake: Family Home w/ Grill

2 Mi to Stockton Lake: Family Home w/ Grill
3.0 star property
Stockton
The price is NZ$331
includes taxes & fees
10 May - 11 May
2 Mi to Stockton Lake: Family Home w/ Grill

Cabin 10 - Reel and Trigger

Cabin 10 - Reel and Trigger
Tom Township
10.0 out of 10, Exceptional, (1 review)
"We had family camping at the state park for the long weekend and wanted to stay close by. The cabin was perfect. We had time to visit easily and also an air conditioned place to sleep in. It also is dog friendly so we were able to bring the dogs. Getting a dog sitter on a long weekend is difficult. "
United States
Audrey B.
The price is NZ$269
includes taxes & fees
6 May - 7 May
Cabin 10 - Reel and Trigger

Peace on the River: King Bed, Dogs Ok (Cabin 3)

Peace on the River: King Bed, Dogs Ok (Cabin 3)
Stockton
The price is NZ$347
includes taxes & fees
10 May - 11 May
Peace on the River: King Bed, Dogs Ok (Cabin 3)

Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.

Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.
Deepwater
10.0 out of 10, Exceptional, (46 reviews)
"Beautiful had everything we needed and was very peaceful "
United States
Raelynn W.
The price is NZ$458
includes taxes & fees
10 May - 11 May
Newly Renovated Cabin on Truman Lake Warsaw, Clinton, Bucksaw.

Cute Family Cabin at Lakeview by Sue

Cute Family Cabin at Lakeview by Sue
Appleton City
10.0 out of 10, Exceptional, (8 reviews)
"This place was fantastic. We will return again next year. "
United States
Lee C.
The price is NZ$320
includes taxes & fees
10 May - 11 May
Cute Family Cabin at Lakeview by Sue

Cozy Home w/ Doggy Fence

Cozy Home w/ Doggy Fence
Warsaw
9.0 out of 10, Wonderful, (60 reviews)
"We enjoyed our stay this was our second time look forward to doing again. "
United States
Gloria G.
The price is NZ$305
includes taxes & fees
13 May - 14 May
Cozy Home w/ Doggy Fence

Hickory Hollow Resort

Hickory Hollow Resort
2.0 star property
Clinton
8.2 out of 10, Very good, (17 reviews)
"Nice place to stay "
United States
Sam
The price is NZ$154
includes taxes & fees
5 June - 6 June
Hickory Hollow Resort

Charming 3-bedroom cabin in delightful Stockton with WiFi, AC,

Charming 3-bedroom cabin in delightful Stockton with WiFi, AC,
Stockton, MO 65785
8.6 out of 10, Excellent, (34 reviews)
"Overall we really liked the property."
United States
Jessica W.
The price is NZ$254
includes taxes & fees
12 May - 13 May
Charming 3-bedroom cabin in delightful Stockton with WiFi, AC,

Stockton Lakes’ Rustic Retreat - Cozy & Close

Stockton Lakes’ Rustic Retreat - Cozy & Close
Stockton
10.0 out of 10, Exceptional, (14 reviews)
"Great place to stay!"
United States
Deanna C.
The price is NZ$475
includes taxes & fees
10 May - 11 May
Stockton Lakes’ Rustic Retreat - Cozy & Close

Barndominium on the lake

Barndominium on the lake
Flemington
9.4 out of 10, Exceptional, (3 reviews)
"We enjoyed the peace and quiet here! Our kids were able to be outside and enjoy the property. Beautiful place to stay and we plan to be back!"
United States
Brittany S.
The price is NZ$435
includes taxes & fees
7 May - 8 May
Barndominium on the lake

2 Mi to Stockton Lake: Family Home w/ Grill

2 Mi to Stockton Lake: Family Home w/ Grill
Stockton
The price is NZ$335
includes taxes & fees
10 May - 11 May
2 Mi to Stockton Lake: Family Home w/ Grill

Rolly's house home away from home

Rolly's house home away from home
Warsaw
8.0 out of 10, Very good, (2 reviews)
"It was a nice little old house . I thought it was better then a hotel for sure no body banging doors or any other ppl to worry about so that was nice "
United States
Kevin C.
The price is NZ$272
includes taxes & fees
6 May - 7 May
Rolly's house home away from home
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

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, 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 NZ$243 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?

Whole house on a quiet cove, Lake of the Ozarks, Family owned and operated.: This holiday home rental outside of Osceola is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Osceola?

Harry S Truman Reservoir 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.