Osceola Vacation Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Osceola vacation rentals

A house by a lake with a covered porch and a satellite dish.

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 SAR 450
SAR 678 total
includes taxes & fees
15 Nov - 16 Nov
Cozy pond house nestled in nature waiting for you to enjoy
A compact kitchen with a wooden table, two stools, a refrigerator, a microwave, and an oven.

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, (24 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 SAR 439
SAR 666 total
includes taxes & fees
12 Nov - 13 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
2-bedroom apartment close to uptown Creston with WiFi and off street parking.
A living room with a sofa, a coffee table, a TV, and a dining area with chairs and a table.

4. Adair Hideaway : Quiet Neighborhood - Fenced Yard

Adair Hideaway : Quiet Neighborhood - Fenced Yard
Creston
10.0 out of 10, Exceptional, (12 reviews)
"We absolutely loved our stay. The place was clean and comfortable. Very peaceful and quiet."
United States
Ana M.
The price is SAR 488
SAR 816 total
includes taxes & fees
1 Dec - 2 Dec
Adair Hideaway : Quiet Neighborhood - Fenced Yard
A garden with a stream, rocks, and flowers.

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 SAR 432
SAR 698 total
includes taxes & fees
9 Nov - 10 Nov
Beautiful Rustic Barn just waiting for you to kick back and relax.
A two-story house with a front porch, a red garage door, and a brick wall with a star emblem.

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, (21 reviews)
"Very nice place to stay."
United States
Todd W.
The price is SAR 466
SAR 758 total
includes taxes & fees
9 Nov - 10 Nov
Spacious Farmhouse beautifully decorated waiting for laughs and memories
A kitchen with wooden cabinets, a stove, and various kitchen appliances.

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 SAR 507
SAR 654 total
includes taxes & fees
9 Nov - 10 Nov
The Hen House Country Living with Farm Life Appeal Indianola, IA
A deck with a table and chairs, surrounded by a wooden deck and a white railing.

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 SAR 378
SAR 1,163 total
includes taxes & fees
9 Nov - 10 Nov
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
A modern hotel room with a large bed, a wooden headboard, a flat-screen TV, a bedside table, and a mirror.

9. Charming Highland

Charming Highland
Corydon
10.0 out of 10, Exceptional, (1 review)
"An excellent and communicative host in a wonderful spot in downtown Corydon."
United States
Joe C.
The price is SAR 488
SAR 560 total
includes taxes & fees
9 Nov - 10 Nov
Charming Highland
A wooden hallway with a painting on the left, a mirror, and a door on the right.

10. 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 SAR 287
SAR 408 total
includes taxes & fees
11 Nov - 12 Nov
Pleasant 3-bedroom bungalow with AC in charming Clearfield
A spacious living area with a red sofa, wooden flooring, a flat-screen TV, and a large window with blinds.

11. • 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 kitchen with wooden cabinets, a refrigerator, a microwave, a stove, and a sink.

12. “Call” it Home: Historic Downtown Apartment

“Call” it Home: Historic Downtown Apartment
Mount Ayr
The price is SAR 582
SAR 702 total
includes taxes & fees
11 Nov - 12 Nov
“Call” it Home: Historic Downtown Apartment
A wooden door leading to a porch with a view of a grassy landscape and a body of water.

13. 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 SAR 563
SAR 851 total
includes taxes & fees
9 Nov - 10 Nov
Cabin close to Lake Rathbun #4
A modern living room with a dining area, a sofa, a coffee table, and a fireplace.

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 SAR 331
SAR 454 total
includes taxes & fees
13 Nov - 14 Nov
Cozy studio loft apartment in rural Iowa with beautiful sunrise and sunset views
A log cabin room with a bed, a fireplace, a television, and a window with blinds.

15. The Gobbler Cabin - Hidden Acres Cabins

The Gobbler Cabin - Hidden Acres Cabins
Bethany
9.0 out of 10, Wonderful, (15 reviews)
"Great cabin! Very clean, loved the pond with ducks! Thank you!"
United States
Brandee M.
The price is SAR 526
SAR 612 total
includes taxes & fees
9 Nov - 10 Nov
The Gobbler Cabin - Hidden Acres Cabins
A wooden door leading to a porch with a view of a grassy landscape and a body of water.

16. 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 SAR 563
SAR 851 total
includes taxes & fees
9 Nov - 10 Nov
Cabin close to Lake Rathbun #3
A wooden door leading to a porch with a view of a grassy landscape and a body of water.

17. 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 SAR 563
SAR 851 total
includes taxes & fees
9 Nov - 10 Nov
Cabin close to Lake Rathbun #6
A wooden door leading to a porch with a view of a grassy landscape and a body of water.

18. 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 SAR 563
SAR 851 total
includes taxes & fees
16 Nov - 17 Nov
Cabin close to Lake Rathbun #1
A wooden door leading to a porch with a view of a grassy landscape and a body of water.

19. 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 SAR 563
SAR 851 total
includes taxes & fees
11 Nov - 12 Nov
Cabin close to Lake Rathbun #2
A wooden cabin interior with a living room, kitchen, and dining area.

20. 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 SAR 751
SAR 874 total
includes taxes & fees
16 Nov - 17 Nov
The Caribou 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 hotel entrance with a stone facade, a sign above the entrance, and a covered walkway.
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.