Osceola Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 10 - Dec 11
Tomorrow
Dec 11 - Dec 12
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Our top choices for Osceola vacation rentals

Property grounds
Serenity Heights - Peaceful Country Acres with beautiful view in every direction

Serenity Heights - Peaceful Country Acres with beautiful view in every direction

Serenity Heights - Peaceful Country Acres with beautiful view in every direction
Osceola
10.0 out of 10, Exceptional, (83)
"Beautiful property with great patios. "
United States
Chris S.
The price is ￥35,053
￥60,525 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Serenity Heights - Peaceful Country Acres with beautiful view in every direction
Private kitchen
Cozy pond house nestled in nature waiting for you to enjoy

Cozy pond house nestled in nature waiting for you to enjoy

Cozy pond house nestled in nature waiting for you to enjoy
2.0 star property
Osceola
The price is ￥16,358
￥26,173 total
includes taxes & fees
Dec 16 - Dec 17
Cozy pond house nestled in nature waiting for you to enjoy
Property grounds
The Little Brick House - Walkable to the Square Dining & Shopping

The Little Brick House - Walkable to the Square Dining & Shopping

The Little Brick House - Walkable to the Square Dining & Shopping
Winterset
10.0 out of 10, Exceptional, (3)
"This was an amazing house to rent. It was super cute and clean. It was walkable to the downtown. We stayed during the Bridges of Madison County festival and we were able to walk there. The host was great at communicating. I would stay here again and would recommend it to anyone visiting Winterset. "
United States
Melinda E.
The Little Brick House - Walkable to the Square Dining & Shopping
Property grounds
Beautiful Rustic Barn just waiting for you to kick back and relax.

Beautiful Rustic Barn just waiting for you to kick back and relax.

Beautiful Rustic Barn just waiting for you to kick back and relax.
NEW VIRGINIA
10.0 out of 10, Exceptional, (404)
"Needed a a quick getaway....it was perfect "
United States
Lee F.
The price is ￥17,916
￥29,935 total
includes taxes & fees
Dec 14 - Dec 15
Beautiful Rustic Barn just waiting for you to kick back and relax.
Exterior
Cabin close to Lake Rathbun #3

Cabin close to Lake Rathbun #3

Cabin close to Lake Rathbun #3
Melrose
10.0 out of 10, Exceptional, (7)
"It was the perfect place for a getaway with my wife"
United States
Michael C.
Cabin close to Lake Rathbun #3
Exterior
≋ The Cottage at Sun Valley Lake ≋

≋ The Cottage at Sun Valley Lake ≋

≋ The Cottage at Sun Valley Lake ≋
Ellston
10.0 out of 10, Exceptional, (75)
"Absolutely beautiful place. "
United States
A P.
≋ The Cottage at Sun Valley Lake ≋
Fridge, microwave, oven, stovetop
The Caribou Cabin - Hidden Acres Cabins

The Caribou Cabin - Hidden Acres Cabins

The Caribou Cabin - Hidden Acres Cabins
Bethany
10.0 out of 10, Exceptional, (1)
"The property manager was prompt and courteous. The property was clean and comfortable."
United States
michelle c.
The price is ￥31,158
￥37,966 total
includes taxes & fees
Dec 16 - Dec 17
The Caribou Cabin - Hidden Acres Cabins
Interior
Cabin close to Lake Rathbun #2

Cabin close to Lake Rathbun #2

Cabin close to Lake Rathbun #2
Melrose
9.8 out of 10, Exceptional, (16)
"The area was secluded and quiet and the cabin was clean and well maintained. We enjoyed our stay and the fire pit out back. "
United States
Melissa B.
The price is ￥23,369
￥37,460 total
includes taxes & fees
Dec 16 - Dec 17
Cabin close to Lake Rathbun #2
WiFi, bed sheets
The Gobbler Cabin - Hidden Acres Cabins

The Gobbler Cabin - Hidden Acres Cabins

The Gobbler Cabin - Hidden Acres Cabins
Bethany
9.8 out of 10, Exceptional, (6)
"Great stay. Clean and nice property. "
United States
JA W.
The price is ￥21,811
￥26,639 total
includes taxes & fees
Dec 12 - Dec 13
The Gobbler Cabin - Hidden Acres Cabins
Property grounds
Quiet Escape Near Rathbun Lake & Public Hunting Grounds

Quiet Escape Near Rathbun Lake & Public Hunting Grounds

Quiet Escape Near Rathbun Lake & Public Hunting Grounds
Russell
10.0 out of 10, Exceptional, (1)
"It was a great experience "
United States
Mark N.
Quiet Escape Near Rathbun Lake & Public Hunting Grounds
TV, fireplace
The Elk Cabin - Hidden Acres Cabins

The Elk Cabin - Hidden Acres Cabins

The Elk Cabin - Hidden Acres Cabins
Bethany
10.0 out of 10, Exceptional, (1)
"Yes and yes, everything was good. However, it was not Nove 12-19,, , it was Nov 13-20"
United States
joseph h.
The price is ￥24,926
￥30,466 total
includes taxes & fees
Dec 12 - Dec 13
The Elk Cabin - Hidden Acres Cabins
Fridge, microwave, oven, stovetop
The Hen House Country Living with Farm Life Appeal Indianola, IA

The Hen House Country Living with Farm Life Appeal Indianola, IA

The Hen House Country Living with Farm Life Appeal Indianola, IA
Indianola
10.0 out of 10, Exceptional, (7)
"Our host was amazing. Went above to make sure we had a great stay. Very personable..We both enjoyed visiting with her and learning more about the area. We will definitely return to the Hen House"
United States
Madonna
The price is ￥21,032
￥29,772 total
includes taxes & fees
Dec 14 - Dec 15
The Hen House Country Living with Farm Life Appeal Indianola, IA
Private kitchen
blue sky cottage!!!!

blue sky cottage!!!!

blue sky cottage!!!!
Bethany
10.0 out of 10, Exceptional, (4)
"As promoted, Blue Sky Cottage is a mid-1900s gas station renovated into a studio cottage. And what a delightful adaptation of the property - clean, cozy (perfect size for a couple), bright (lots of light in and reflected), well-furnished and stocked, and even a small patio for enjoying the outdoors. Also a great location for our forays to Pawnee Prairie and Dunn Ranch Prairie in search of birds (bobolinks quite prevalent in June). We enjoyed trying to figure out which parts of the building were...
United States
Paul H.
blue sky cottage!!!!
Microwave, oven, stovetop, dishwasher
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
Winterset
10.0 out of 10, Exceptional, (4)
"The house was absolutely gorgeous! It was very comfortable and had everything we needed. I would most definitely stay here again!"
United States
Heather G.
The price is ￥14,992
￥49,420 total
includes taxes & fees
Dec 15 - Dec 16
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
Interior
Cabin close to Lake Rathbun #1

Cabin close to Lake Rathbun #1

Cabin close to Lake Rathbun #1
Melrose
10.0 out of 10, Exceptional, (9)
"Loved the stay, Awesome location and great experience. The management was awesome, I would likely rent again."
United States
Jeremy A.
The price is ￥23,369
￥37,460 total
includes taxes & fees
Dec 12 - Dec 13
Cabin close to Lake Rathbun #1
Interior
Looking for a getaway? This property is perfect for your vacation!

Looking for a getaway? This property is perfect for your vacation!

Looking for a getaway? This property is perfect for your vacation!
Weldon
9.8 out of 10, Exceptional, (56)
"Our 4th or 5th stay at the Weldon farm. We love the peace and quiet and will always return here for family visits."
United States
Lisa W.
The price is ￥21,032
￥39,259 total
includes taxes & fees
Dec 12 - Dec 13
Looking for a getaway? This property is perfect for your vacation!
Interior
Cabin close to Lake Rathbun #5

Cabin close to Lake Rathbun #5

Cabin close to Lake Rathbun #5
Melrose
9.6 out of 10, Exceptional, (7)
"Perfect for a quick stay while on a fishing trip. "
United States
Ryan D.
Cabin close to Lake Rathbun #5
Fridge, microwave, oven, stovetop
The Bear Cabin - Hidden Acres Cabins

The Bear Cabin - Hidden Acres Cabins

The Bear Cabin - Hidden Acres Cabins
Bethany
10.0 out of 10, Exceptional, (1)
"Clean accommodations, comfy beds, and beautiful location. A couple questions I had for the owner were answered immediately. We will definitely book here next time we come through this area!"
United States
Melody Z.
The price is ￥31,158
￥37,966 total
includes taxes & fees
Dec 16 - Dec 17
The Bear Cabin - Hidden Acres Cabins
House (4 Bedrooms) | Interior
Charming Winterset Vacation Rental w/ Yard & Patio

Charming Winterset Vacation Rental w/ Yard & Patio

Charming Winterset Vacation Rental w/ Yard & Patio
3.0 star property
Winterset
10.0 out of 10, Exceptional, (1)
"We stayed here on a trip for the Knoxville Nationals. Went to the John Wayne Museum, seen the bridges. The house is a nice house, met many locals at the pharmacy-resturaunt in the square downtown, very friendly, ate at several other local spots, all good service and food. The area is quiet and the house in great shape, clean, had plenty of towels and comfortable beds. Would definitely recommend if you need a place in this area. "
United States
Tracy
Charming Winterset Vacation Rental w/ Yard & Patio
Exterior
Cabin close to Lake Rathbun #4

Cabin close to Lake Rathbun #4

Cabin close to Lake Rathbun #4
Melrose
9.2 out of 10, Wonderful, (7)
"Cabin rented for parents to stay to celebrate fathers birthday at Rathbun."
United States
Tara D.
Cabin close to Lake Rathbun #4
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
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

Family Budget Inn Bethany

Family Budget Inn Bethany

10/10 Excellent
"Great stay"
Marcy 1-night trip
Posted 12 hours ago
Family Budget Inn Bethany

Find out more about Osceola

Search for holiday rentals in Osceola on Expedia! You can easily find your home rentals, villas, holiday apartments in Osceola using one of the methods below:

  • View our selection of featured holiday rentals in Osceola
  • Use the map to find apartments and other holiday homes in the Osceola neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Osceola while they last

Look no further and take a look at our great range of rental properties in Osceola!

Frequently asked questions

Can I find vacation rentals in Osceola?

Yes, there are vacation rentals near popular attractions in Osceola, or you can select a more remote option if you're looking for a relaxing stay. Visitors to Osceola speak positively about the lakeside and restaurants in this destination. Make sure you have time to check out the casinos and golf courses during your trip.

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

Serenity Heights - Peaceful Country Acres with beautiful view in every direction: This highly rated vacation home rental in Osceola is located in a rural location and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Osceola?

Grade Lake and West Lake are a couple of lovely local spots to get outside and enjoy nature. While here, Osceola Country Club and Lakeside Casino are other places worth a visit.

What are vacation rentals like in Osceola?

Vacation rentals are privately owned accommodations you can book for a few days or a quick weekend in Osceola. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a small group gathering.