Osceola Vacation Rentals

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Check prices for these dates

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

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.
$167 nightly
The price is $175
Nov 15 - Nov 16
Total with taxes and fees
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, (25 reviews)
"Very clean, comfortable, and accommodating host. We will be staying here again in the future for sure!"
United States
Mark O.
$165 nightly
The price is $173
Nov 12 - Nov 13
Total with taxes and fees
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
$157 nightly
The price is $176
Nov 29 - Nov 30
Total with taxes and fees
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.
$189 nightly
The price is $212
Nov 29 - Nov 30
Total with taxes and fees
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.
$172 nightly
The price is $181
Nov 10 - Nov 11
Total with taxes and fees
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.
$186 nightly
The price is $196
Nov 11 - Nov 12
Total with taxes and fees
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.
$168 nightly
The price is $176
Nov 10 - Nov 11
Total with taxes and fees
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.
$267 nightly
The price is $300
Nov 30 - Dec 1
Total with taxes and fees
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.
$139 nightly
The price is $146
Nov 10 - Nov 11
Total with taxes and fees
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.
$102 nightly
The price is $107
Nov 11 - Nov 12
Total with taxes and fees
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.
$253 nightly
The price is $283
Dec 5 - Dec 6
Total with taxes and fees
• 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
$163 nightly
The price is $183
Nov 11 - Nov 12
Total with taxes and fees
“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.
$210 nightly
The price is $221
Nov 10 - Nov 11
Total with taxes and fees
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
$112 nightly
The price is $118
Nov 13 - Nov 14
Total with taxes and fees
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.
$148 nightly
The price is $159
Nov 10 - Nov 11
Total with taxes and fees
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.
$210 nightly
The price is $221
Nov 10 - Nov 11
Total with taxes and fees
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.
$210 nightly
The price is $221
Nov 10 - Nov 11
Total with taxes and fees
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.
$210 nightly
The price is $221
Nov 16 - Nov 17
Total with taxes and fees
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.
$210 nightly
The price is $221
Nov 11 - Nov 12
Total with taxes and fees
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
$207 nightly
The price is $223
Nov 16 - Nov 17
Total with taxes and fees
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

Find out more about Osceola

Everything you need to know about Osceola vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osceola vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osceola vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osceola vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osceola. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Osceola in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $106 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osceola rentals

At Expedia, we put the best Osceola vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osceola rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osceola vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osceola. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

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