Photo by Kelly Lasswell

Holiday Homes in Osceola

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct

Featured Holiday Homes in Osceola

Our top choices for Osceola holiday homes

Cozy Home w/ Doggy Fence
Outdoor dining

Cozy Home w/ Doggy Fence

9.2 out of 10, Wonderful, (53)
"House was clean and had everything we needed to make our stay comfortable! "
The price is AU$280
includes taxes & fees
8 Sept - 9 Sept
Cozy Home w/ Doggy Fence
Stockton Lake Getaway Less than 1/2 mi to Lake
Terrace/patio

Stockton Lake Getaway Less than 1/2 mi to Lake

10.0 out of 10, Exceptional, (5)
"The cabin was amazing everything you need issupplied it is wonderful and with a warm cozy feel "
The price is AU$684
includes taxes & fees
25 Sept - 26 Sept
Stockton Lake Getaway Less than 1/2 mi to Lake
This house is a 2 bedroom(s), 2 bathrooms, located in Fair Play, MO.
Fridge, microwave, oven, stovetop

This house is a 2 bedroom(s), 2 bathrooms, located in Fair Play, MO.

10.0 out of 10, Exceptional, (1)
"Very nice house, clean, and spacious."
The price is AU$808
includes taxes & fees
3 Sept - 4 Sept
This house is a 2 bedroom(s), 2 bathrooms, located in Fair Play, MO.
Rm 3 - Waterfront Double Queen / 2nd floor
Property grounds

Rm 3 - Waterfront Double Queen / 2nd floor

10.0 out of 10, Exceptional, (6)
"Really enjoyed our overnight stay here. Very friendly and beautiful view. Dock was peaceful at night. Didn't have time to fish, unfortunately - but the setup looks fantastic."
The price is AU$225
includes taxes & fees
6 Sept - 7 Sept
Rm 3 - Waterfront Double Queen / 2nd floor
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (16)
"House itself is amazing. Stayed here prior to Katy Trail ride- only 1.5 miles from the trailhead. Neighborhood is sketchy looking but no issues other than appearance."
The price is AU$247
includes taxes & fees
8 Sept - 9 Sept
The Orchard House: Close to the Katy Trail, Truman Lake and Historic Downtown
Charming 2-bedroom house with WiFi and AC in Warsaw close to launch ramps
Microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (1)
"Liked long driveway and easy access. Clean comfy respectable place. Communication was great!! "
The price is AU$379
includes taxes & fees
8 Sept - 9 Sept
Charming 2-bedroom house with WiFi and AC in Warsaw close to launch ramps
Rm 2 -Waterfront Double Queen / 2nd floor
Property grounds

Rm 2 -Waterfront Double Queen / 2nd floor

10.0 out of 10, Exceptional, (4)
"Very clean and greats hosts! We will be coming back!"
The price is AU$225
includes taxes & fees
7 Sept - 8 Sept
Rm 2 -Waterfront Double Queen / 2nd floor
2-bedroom vacation home just 8 minutes from Stockton Lake
Exterior

2-bedroom vacation home just 8 minutes from Stockton Lake

9.8 out of 10, Exceptional, (9)
"An outstanding place to stay, and such lovely people to host! Seriously, they were extremely accommodating and so amazing "
The price is AU$200
includes taxes & fees
31 Aug - 1 Sept
2-bedroom vacation home just 8 minutes from Stockton Lake
Lake House on Truman Lake
Fridge, microwave, oven, stovetop

Lake House on Truman Lake

10.0 out of 10, Exceptional, (4)
"House was described very well and did not disappoint."
Lake House on Truman Lake
Cedar Lodge is quaint rustic lodge with modern amenities. Relaxing and warm!
Interior

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

10.0 out of 10, Exceptional, (80)
"A wonderful stay- highly recommend for anyone visiting the area!"
The price is AU$228
includes taxes & fees
28 Aug - 29 Aug
Cedar Lodge is quaint rustic lodge with modern amenities. Relaxing and warm!
Peaceful Lakefront Cabin
Fridge, microwave, oven, stovetop

Peaceful Lakefront Cabin

9.6 out of 10, Exceptional, (5)
"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. "
The price is AU$621
includes taxes & fees
28 Aug - 29 Aug
Peaceful Lakefront Cabin
Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw
Property grounds

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

The price is AU$470
includes taxes & fees
10 Sept - 11 Sept
Fisherman’s Paradise at The Lake. Charming 2 bedroom house by the lake in Warsaw
Hunters Paradise on The Lake. Cozy 2 bedroom house with large back yard
Property grounds

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

The price is AU$470
includes taxes & fees
10 Sept - 11 Sept
Hunters Paradise on The Lake. Cozy 2 bedroom house with large back yard
T's Fish Camp--Crappie Are Biting—Sleeps up to Six
Property grounds

T's Fish Camp--Crappie Are Biting—Sleeps up to Six

10.0 out of 10, Exceptional, (26)
"We went as a guys trip and it was perfect to get on the water and to clean fish etc. owners are wonderful at communicating and accommodating! Thank you!! "
The price is AU$289
includes taxes & fees
10 Sept - 11 Sept
T's Fish Camp--Crappie Are Biting—Sleeps up to Six
Stockton Lakes’ Rustic Retreat - Cozy & Close
Exterior detail

Stockton Lakes’ Rustic Retreat - Cozy & Close

10.0 out of 10, Exceptional, (11)
"Great place to stay!"
The price is AU$410
includes taxes & fees
28 Aug - 29 Aug
Stockton Lakes’ Rustic Retreat - Cozy & Close
Brand New Home near Truman Lake with New Hot Tub, Access to Boat Ramp/Marina.
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (12)
"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!"
The price is AU$603
includes taxes & fees
28 Aug - 29 Aug
Brand New Home near Truman Lake with New Hot Tub, Access to Boat Ramp/Marina.
Minutes away from Stockton Lake
Terrace/patio

Minutes away from Stockton Lake

10.0 out of 10, Exceptional, (10)
"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!"
The price is AU$516
includes taxes & fees
2 Sept - 3 Sept
Minutes away from Stockton Lake
The Lodge - Large Rental
Living area

The Lodge - Large Rental

10.0 out of 10, Exceptional, (1)
"Had 10 people in the house plenty of room will definitely be staying there again"
The price is AU$814
includes taxes & fees
7 Sept - 8 Sept
The Lodge - Large Rental
Modern and Spacious with game/movie room.
Fridge, microwave, oven, stovetop

Modern and Spacious with game/movie room.

10.0 out of 10, Exceptional, (5)
"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!"
The price is AU$638
includes taxes & fees
27 Sept - 28 Sept
Modern and Spacious with game/movie room.
Modern luxury vacation home
Terrace/patio

Modern luxury vacation home

10.0 out of 10, Exceptional, (6)
"This property was perfect for our weekend trip to the lake with a couple of friends. Great outside area and very private."
The price is AU$513
includes taxes & fees
27 Sept - 28 Sept
Modern luxury vacation 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osceola Hotel Reviews

Find out more about Osceola

Find out more about Osceola

Osceola Holiday Homes information

Number of reviews
419
Accommodation
91 Holiday Homes
Lowest Price
AU$225
Highest Price
AU$379

Explore a world of travel with Expedia

Explore a world of travel with Expedia