Photo by Kelly Lasswell

Osceola Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Osceola

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

10.0 out of 10, Exceptional, (11)
"Was a great place to get away. This is for hunters and fishermen. My wife and myself found this place and thought how nice. Glad we did! Awesome host no better. Definitely will revisit in the future. Quit and secluded away from all👍"
Secluded Hunting & Fishing cabin in the Woods - Osceola, MO

Historic Commercial Hotel(Est. 1868)Tom Mix Suite

9.8 out of 10, Exceptional, (15)
"Property is very nice. A short walk to a playground by the lake. One block to a nice Mexican Restaurant and one block to a coffee house and a very awesome barber shop where my great grandson got his first haircut. We found out later that his dad had his very first haircut there too. Enjoyed the comfy beds."
The price is AU$191
includes taxes & fees
29 Nov - 30 Nov
Historic Commercial Hotel(Est. 1868)Tom Mix Suite

Lake of the Ozarks Home - waterfront with dock

9.4 out of 10, Exceptional, (57)
"Very clean, great communication. "
Lake of the Ozarks Home - waterfront with dock

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

10.0 out of 10, Exceptional, (8)
"Loved this little home tucked away! "
The price is AU$265
includes taxes & fees
27 Dec - 28 Dec
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown

CABIN IN THE WOODS , FAMILY AND PET FRIENDLY

9.8 out of 10, Exceptional, (58)
"Did not expect the back ride to be as nice as it was. Lots of fire wood, lots of room to sit around the fire pit and plenty of chair provided. Nicely lit. Lovely back covered deck. Great for grilling and out door dining "
CABIN IN THE WOODS , FAMILY AND PET FRIENDLY

Wolf Cub Cab of Pomme de Terre

9.4 out of 10, Exceptional, (95)
"Checked in and everything was how it was described, we will definitely come and stay again in the future "
Wolf Cub Cab of Pomme de Terre

Pet-Friendly Flemington Home w/ Lake Access!

9.8 out of 10, Exceptional, (19)
"Property is clean on the inside. The outside needs some plants tended to by thinning and cutting them back."
Pet-Friendly Flemington Home w/ Lake Access!

Lake view Stockton cabin. Close to water.

9.0 out of 10, Wonderful, (13)
"Very comfortable and cozy. Nice and relaxing and close to town. We were in town for rodeo finals so didn’t get to enjoy the lake or stay at the home very much but while we were there it was perfect "
Lake view Stockton cabin. Close to water.

Hill Top Haven Dock!! Lake access!!

9.2 out of 10, Wonderful, (100)
"It was very comfortable and cozy place to stay. We had a great time."
Hill Top Haven Dock!! Lake access!!

The Cabin by Bucksaw Marina, Truman Lake

The Cabin by Bucksaw Marina, Truman Lake

Wolf Pack place of Pomme de Terre Lake!

9.4 out of 10, Exceptional, (80)
"This cabin was absolutely darling. The private spa hot tub was put ti good use on our anniversary weekend! It was peaceful and relaxing. Will definitely be back. "
Wolf Pack place of Pomme de Terre Lake!

Cedar Ridge, 3BR 2 Bath Cabin on Truman Lake

9.8 out of 10, Exceptional, (11)
"Great stay, peaceful and relaxing great for family "
Cedar Ridge, 3BR 2 Bath Cabin on Truman Lake

Caddyshack - Located on Stockton Golf Course

10.0 out of 10, Exceptional, (22)
"We had a great stay. Tami was very accommodating and kind. "
Caddyshack - Located on Stockton Golf Course

Cabin house on a quiet cove - Lake of the Ozarks near Warsaw

10.0 out of 10, Exceptional, (51)
"Beautiful spot"
Cabin house on a quiet cove - Lake of the Ozarks near Warsaw

Lake house with a view! Overlooks Warsaw and Lake of the Ozarks, Sleeps 4

10.0 out of 10, Exceptional, (33)
"The house was clean and pleasant the neighborhood looked sketchy but had no problems"
Lake house with a view! Overlooks Warsaw and Lake of the Ozarks, Sleeps 4

'Lazy RS Lakehouse' w/ Private Hot Tub & Boat Dock

9.8 out of 10, Exceptional, (18)
"Wonderful stay! Owners were easily to access and helpful with any questions. Very responsive. Check out is the EASIEST I’ve had in years of using VRBO. Will book again. "
'Lazy RS Lakehouse' w/ Private Hot Tub & Boat Dock

Cheerful Carefree Cottage with Stunning Lake Views

9.8 out of 10, Exceptional, (53)
"Loved watching the sunset or “show” each night. Just lovely."
Cheerful Carefree Cottage with Stunning Lake Views

Water front Lake of the Ozarks Studio Apartment

10.0 out of 10, Exceptional, (21)
"Stay for a few days, Very quite place, clean and host was friendly."
Water front Lake of the Ozarks Studio Apartment

Warsaw Cabin w/ Sunroom & Lake Access!

9.6 out of 10, Exceptional, (5)
"The propery was very nice. The rooms were great and we loved that there were fans and AC units in all the rooms. The area was decently quiet. We spent most of our time on the screened porch for meals and just hanging out. Love that it was pet friendly and that we could bring our dogs"
Warsaw Cabin w/ Sunroom & Lake Access!

Cozy Home w/ Boat Parking 5mins From Truman Dam

9.0 out of 10, Wonderful, (44)
"Cute lil cabin atmosphere 5 min from Truman dam. Perfect for us and our dog pack. Owner was very pleasant. Will come back"
Cozy Home w/ Boat Parking 5mins From Truman Dam
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.
Don't see what you're looking for?
See all available properties in Osceola
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Osceola you may be interested in

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

10.0 out of 10, Exceptional, (11)
"Was a great place to get away. This is for hunters and fishermen. My wife and myself found this place and thought how nice. Glad we did! Awesome host no better. Definitely will revisit in the future. Quit and secluded away from all👍"
Secluded Hunting & Fishing cabin in the Woods - Osceola, MO

Historic Commercial Hotel(Est. 1868)Tom Mix Suite

9.8 out of 10, Exceptional, (15)
"Property is very nice. A short walk to a playground by the lake. One block to a nice Mexican Restaurant and one block to a coffee house and a very awesome barber shop where my great grandson got his first haircut. We found out later that his dad had his very first haircut there too. Enjoyed the comfy beds."
The price is AU$191
includes taxes & fees
29 Nov - 30 Nov
Historic Commercial Hotel(Est. 1868)Tom Mix Suite

Westbridge Inn and Suites

2.0 star property
8.0 out of 10, Very good, (556)
"Really enjoyed the jacuzzi tub and size of the room"
The price is AU$133
includes taxes & fees
10 Dec - 11 Dec
Westbridge Inn and Suites
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Lake of the Ozarks Home - waterfront with dock: This holiday home rental outside of Osceola is located on a lake, and has a balcony, a selection of games 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. Make the most of Access to hot tub in this rental home to help you unwind.

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. Turkey Creek State Wildlife Area and Crowes Crossing Public Use 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.