Osceola Holiday 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 holiday 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 AU$263
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 AU$262
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
The price is AU$286
includes taxes & fees
28 Nov - 29 Nov
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 AU$318
includes taxes & fees
29 Nov - 30 Nov
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 AU$273
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 AU$296
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 AU$255
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 AU$452
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 AU$219
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 AU$160
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.
The price is AU$431
includes taxes & fees
5 Dec - 6 Dec
• 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 AU$274
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 AU$328
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 AU$178
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 AU$239
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 AU$328
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 AU$328
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 AU$331
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 AU$328
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 AU$340
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 living room with a stone wall, a fireplace, a flat-screen TV, and two patterned armchairs.
Cobblestone Inn & Suites - Lamoni

Cobblestone Inn & Suites - Lamoni

Cobblestone Inn & Suites - Lamoni
Lamoni

10/10 Excellent

Second visit here great staff and great facilities
Australia
Anonymous traveller
Reviewed January 9, 2019
Cobblestone Inn & Suites - Lamoni

Find out more about Osceola

Everything you need to know about Osceola holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osceola holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Osceola holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osceola holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osceola holiday rentals we have selected for you start as low as AU$160 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Osceola rentals

At Expedia, we put the best Osceola holiday 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 holiday.

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 holiday rentals in Osceola?

Yes, there are holiday rentals close to the most popular sights in Osceola, or you can select a more secluded 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 holiday rentals that Osceola has to offer?

Serenity Heights - Peaceful Country Acres with beautiful view in every direction: This highly rated holiday home rental in Osceola is located in a rural location, and has a fireplace, a balcony and a BBQ 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 that 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 holiday rentals like in Osceola?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osceola. Holiday rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.