Osceola Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Osceola vacation rentals

A wooden deck with potted plants and carved pumpkins by a lake.

1. Cozy pond house nestled in nature waiting for you to enjoy

Cozy pond house nestled in nature waiting for you to enjoy
Osceola
9.8 out of 10, Exceptional, (6 reviews)
"It was more than we expected, a perfect place to get away for some peace and quiet. Super clean and very well equipped with everything we needed. Can't wait to stay again!"
United States
Eric F.
The price is AED 397
AED 613 total
includes taxes & fees
15 Nov - 16 Nov
Cozy pond house nestled in nature waiting for you to enjoy
A wooden deck with a table and chairs, surrounded by greenery and a wooden pergola with string lights.

2. Charming 3-bedroom house in Decatur City, Minutes from Little River Lake.

Charming 3-bedroom house in Decatur City, Minutes from Little River Lake.
Decatur City
10.0 out of 10, Exceptional, (25 reviews)
"Very clean, comfortable, and accommodating host. We will be staying here again in the future for sure!"
United States
Mark O.
The price is AED 477
AED 706 total
includes taxes & fees
19 Nov - 20 Nov
Charming 3-bedroom house in Decatur City, Minutes from Little River Lake.
A staircase with white railings and a potted plant at the bottom.

3. 2-bedroom apartment close to uptown Creston with WiFi and off street parking.

2-bedroom apartment close to uptown Creston with WiFi and off street parking.
Creston
10.0 out of 10, Exceptional, (10 reviews)
"Great little apartment-like spot for stays on Creston. Easy checkin, clean spot, easy checkout."
United States
Samuel
The price is AED 364
AED 666 total
includes taxes & fees
18 Nov - 19 Nov
2-bedroom apartment close to uptown Creston with WiFi and off street parking.
A kitchen with white cabinets, a stove, and a dishwasher.

4. Adair Hideaway : Quiet Neighborhood - Fenced Yard

Adair Hideaway : Quiet Neighborhood - Fenced Yard
Creston
10.0 out of 10, Exceptional, (13 reviews)
"We absolutely loved our stay. The place was clean and comfortable. Very peaceful and quiet."
United States
Ana M.
The price is AED 477
AED 798 total
includes taxes & fees
18 Nov - 19 Nov
Adair Hideaway : Quiet Neighborhood - Fenced Yard
A house with a red roof and a garden with a pond.

5. 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, (416 reviews)
"This place was so incredibly cute. We loved our little getaway for our first anniversary and we had everything we needed and more. Thank you for providing such a great place, we’ll definitely be back!!"
United States
Genevieve P.
The price is AED 423
AED 683 total
includes taxes & fees
16 Nov - 17 Nov
Beautiful Rustic Barn just waiting for you to kick back and relax.
A covered porch with wicker furniture, columns, and a view of the outdoors.

6. Spacious Farmhouse beautifully decorated waiting for laughs and memories

Spacious Farmhouse beautifully decorated waiting for laughs and memories
New Virginia
10.0 out of 10, Exceptional, (22 reviews)
"Very nice place to stay."
United States
Todd W.
The price is AED 456
AED 745 total
includes taxes & fees
14 Nov - 15 Nov
Spacious Farmhouse beautifully decorated waiting for laughs and memories
A grassy field with trees and a fence in the background.

7. 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, (19 reviews)
"Loved it, every thing was awesome."
United States
Adam b.
The price is AED 496
AED 671 total
includes taxes & fees
15 Nov - 16 Nov
The Hen House Country Living with Farm Life Appeal Indianola, IA
A dining area with a chandelier, wooden chairs, and a table set with plates and a glass dome centerpiece.

8. 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, (15 reviews)
"The house in Winterset was perfect in every way. It was beautifully furnished and extremely comfortable. We are so glad we stayed there."
United States
Nickay M.
The price is AED 336
AED 1,100 total
includes taxes & fees
30 Nov - 1 Dec
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
A wooden hallway with a painting on the left, a mirror, and a door on the right.

9. Pleasant 3-bedroom bungalow with AC in charming Clearfield

Pleasant 3-bedroom bungalow with AC in charming Clearfield
Clearfield
9.6 out of 10, Exceptional, (14 reviews)
"It was a great stay!"
United States
Dustin F.
The price is AED 281
AED 368 total
includes taxes & fees
16 Nov - 17 Nov
Pleasant 3-bedroom bungalow with AC in charming Clearfield
A cozy room with two orange armchairs, a small table, a flat-screen TV displaying Disney+, and a patterned carpet.

10. • Lively Cottage 2 King Beds 4 Bed 2 Bath •

• Lively Cottage 2 King Beds 4 Bed 2 Bath •
Indianola
9.4 out of 10, Exceptional, (24 reviews)
"Had a great stay, will come back!"
United States
Spring A.
• Lively Cottage 2 King Beds 4 Bed 2 Bath •
A bedroom with a bed, a bedside table with a lamp, a ceiling fan, a door, and a wall with a sign.

11. “Call” it Home: Historic Downtown Apartment

“Call” it Home: Historic Downtown Apartment
Mount Ayr
The price is AED 569
AED 687 total
includes taxes & fees
16 Nov - 17 Nov
“Call” it Home: Historic Downtown Apartment
A log cabin with a porch and steps leading to a door.

12. Cabin close to Lake Rathbun #4

Cabin close to Lake Rathbun #4
Melrose
9.4 out of 10, Exceptional, (10 reviews)
"It was amazing.It looked beautiful. We enjoyed ourselves"
United States
Larry H.
The price is AED 551
AED 841 total
includes taxes & fees
16 Nov - 17 Nov
Cabin close to Lake Rathbun #4
A wooden cabin bedroom with a bed, a wooden headboard, and a mirror.

13. The Caribou Cabin - Hidden Acres Cabins

The Caribou Cabin - Hidden Acres Cabins
Bethany
9.6 out of 10, Exceptional, (5 reviews)
"Very nice and very clean. Host was very responsive and helpful. Had a great stay!"
United States
Brandon
The price is AED 735
AED 818 total
includes taxes & fees
16 Nov - 17 Nov
The Caribou Cabin - Hidden Acres Cabins
A wooden staircase with a red warning sign at the top.

14. Cozy studio loft apartment in rural Iowa with beautiful sunrise and sunset views

Cozy studio loft apartment in rural Iowa with beautiful sunrise and sunset views
Clearfield
The price is AED 324
AED 444 total
includes taxes & fees
15 Nov - 16 Nov
Cozy studio loft apartment in rural Iowa with beautiful sunrise and sunset views
A log cabin with a porch and steps leading to a door.

15. Cabin close to Lake Rathbun #3

Cabin close to Lake Rathbun #3
Melrose
10.0 out of 10, Exceptional, (9 reviews)
"Exactly what we were looking for, nice view of the lake."
United States
Zach S.
The price is AED 551
AED 841 total
includes taxes & fees
14 Nov - 15 Nov
Cabin close to Lake Rathbun #3
A log cabin with a porch and steps leading to a deck.

16. Cabin close to Lake Rathbun #2

Cabin close to Lake Rathbun #2
Melrose
9.8 out of 10, Exceptional, (22 reviews)
"Enjoyed our stay."
United States
Missy U.
The price is AED 551
AED 841 total
includes taxes & fees
16 Nov - 17 Nov
Cabin close to Lake Rathbun #2
A log cabin with a porch and steps leading to a deck.

17. Cabin close to Lake Rathbun #1

Cabin close to Lake Rathbun #1
Melrose
9.6 out of 10, Exceptional, (10 reviews)
"Cute cabin exactly as advertised. We would definitely stay again!"
United States
Cassey H.
The price is AED 551
AED 841 total
includes taxes & fees
16 Nov - 17 Nov
Cabin close to Lake Rathbun #1
A log cabin with a porch and steps leading to a deck.

18. Cabin close to Lake Rathbun #6

Cabin close to Lake Rathbun #6
Melrose
9.0 out of 10, Wonderful, (4 reviews)
"Was down near lake Rathbun for a wedding, the cabin was very well maintained, clean, and cozy. Thank you!"
United States
Rylan R.
The price is AED 551
AED 806 total
includes taxes & fees
14 Nov - 15 Nov
Cabin close to Lake Rathbun #6
A small, single-story wooden building with a metal roof, a front door, and a small window.

19. The Elk Cabin - Hidden Acres Cabins

The Elk Cabin - Hidden Acres Cabins
Bethany
10.0 out of 10, Exceptional, (4 reviews)
"Great location, easy access, property was beautiful "
United States
Laura B.
The price is AED 588
AED 656 total
includes taxes & fees
22 Nov - 23 Nov
The Elk Cabin - Hidden Acres Cabins
A spacious kitchen with wooden cabinets, a black refrigerator, a microwave, and a large island with bar stools.

20. The Bear Cabin - Hidden Acres Cabins

The Bear Cabin - Hidden Acres Cabins
Bethany
9.6 out of 10, Exceptional, (7 reviews)
"The place was really clean and had everything we needed. We would definitely stay again!"
United Kingdom
Misty M.
The price is AED 735
AED 855 total
includes taxes & fees
23 Nov - 24 Nov
The Bear Cabin - Hidden Acres Cabins
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

A buffet setup with a bowl of oranges and a container of fruit.
Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA
Winterset

10/10 Excellent

Loved the easy access and first floor room we had. Very quiet building and plenty of choices for breakfast. Staff was very accommodating.
United States
Anonymous traveler
Reviewed July 2, 2021
Cobblestone Inn & Suites - Winterset, IA

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.