Lodging Image

Osceola Holiday Rentals

  • 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

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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)
"Very clean and really nice place. The host is professional and kind. I would definitely stay again."
United States
Mike
The price is HK$902
HK$1,416 total
includes taxes & fees
14 Sept - 15 Sept
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, (23 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 HK$918
HK$1,457 total
includes taxes & fees
15 Sept - 16 Sept
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, (9 reviews)
"Great little apartment-like spot for stays on Creston. Easy checkin, clean spot, easy checkout."
United States
Samuel
The price is HK$776
HK$1,432 total
includes taxes & fees
14 Sept - 15 Sept
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, (11 reviews)
"Nice place"
United States
Dale T.
The price is HK$1,020
HK$1,730 total
includes taxes & fees
14 Sept - 15 Sept
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, (414 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 HK$767
HK$1,340 total
includes taxes & fees
14 Sept - 15 Sept
Beautiful Rustic Barn just waiting for you to kick back and relax.

6. Mulberry Cottage Farm-Stay. A unique farm-stay in Southern Iowa

Mulberry Cottage Farm-Stay. A unique farm-stay in Southern Iowa
Lacona
9.4 out of 10, Exceptional, (9 reviews)
"Everything was awesome "
United States
Richard D.
The price is HK$784
HK$1,070 total
includes taxes & fees
14 Sept - 15 Sept
Mulberry Cottage Farm-Stay. A unique farm-stay in Southern Iowa
A two-story house with a front porch, a red garage door, and a brick wall with a star emblem.

7. 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 HK$931
HK$1,587 total
includes taxes & fees
14 Sept - 15 Sept
Spacious Farmhouse beautifully decorated waiting for laughs and memories
A kitchen with wooden cabinets, a stove, and various kitchen appliances.

8. 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, (18 reviews)
"Loved it, every thing was awesome."
United States
Adam b.
The price is HK$1,059
HK$1,490 total
includes taxes & fees
14 Sept - 15 Sept
The Hen House Country Living with Farm Life Appeal Indianola, IA
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 HK$1,019
HK$1,235 total
includes taxes & fees
14 Sept - 15 Sept
Charming Highland
A spacious living area with a red sofa, wooden flooring, a flat-screen TV, and a large window with blinds.

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, (23 reviews)
"Had a great stay, will come back!"
United States
Spring A.
The price is HK$882
HK$2,007 total
includes taxes & fees
15 Sept - 16 Sept
• Lively Cottage 2 King Beds 4 Bed 2 Bath •
A log cabin room with a bed, a fireplace, a television, and a window with blinds.

11. The Gobbler Cabin - Hidden Acres Cabins

The Gobbler Cabin - Hidden Acres Cabins
Bethany
9.2 out of 10, Wonderful, (11 reviews)
"Great cabin! Very clean, loved the pond with ducks! Thank you!"
United States
Brandee M.
The price is HK$1,098
HK$1,341 total
includes taxes & fees
14 Sept - 15 Sept
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.

12. Cabin close to Lake Rathbun #4

Cabin close to Lake Rathbun #4
Melrose
9.4 out of 10, Exceptional, (9 reviews)
"Cabin rented for parents to stay to celebrate fathers birthday at Rathbun."
United States
Tara D.
The price is HK$1,176
HK$1,861 total
includes taxes & fees
14 Sept - 15 Sept
Cabin close to Lake Rathbun #4
A wooden hallway with a painting on the left, a mirror, and a door on the right.

13. 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, (10 reviews)
"It was a great stay!"
United States
Dustin F.
The price is HK$656
HK$1,010 total
includes taxes & fees
14 Sept - 15 Sept
Pleasant 3-bedroom bungalow with AC in charming Clearfield
A kitchen with a hanging plant, a clock, a framed picture, and various kitchen utensils.

14. Yopp's Hideaway, farm stay near Lake Icaria on 26 acres, w/pond & animal visits.

Yopp's Hideaway, farm stay near Lake Icaria on 26 acres, w/pond & animal visits.
Corning
The price is HK$1,288
HK$2,251 total
includes taxes & fees
16 Sept - 17 Sept
Yopp's Hideaway, farm stay near Lake Icaria on 26 acres, w/pond & animal visits.
A deck with a table and chairs, surrounded by a wooden deck and a white railing.

15. 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 HK$1,364
HK$3,259 total
includes taxes & fees
18 Sept - 19 Sept
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
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 #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 HK$1,176
HK$1,861 total
includes taxes & fees
14 Sept - 15 Sept
Cabin close to Lake Rathbun #6
A cozy cabin interior with a wooden floor, a leather sofa, a wooden dining table with stools, and a kitchen area with wooden cabinets and appliances.

17. 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 HK$1,255
HK$1,518 total
includes taxes & fees
14 Sept - 15 Sept
The Elk Cabin - Hidden Acres Cabins
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 #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 HK$1,176
HK$1,861 total
includes taxes & fees
15 Sept - 16 Sept
Cabin close to Lake Rathbun #2
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 #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 HK$1,176
HK$1,861 total
includes taxes & fees
15 Sept - 16 Sept
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.

20. 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 HK$1,176
HK$1,861 total
includes taxes & fees
15 Sept - 16 Sept
Cabin close to Lake Rathbun #1
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

Super 8 by Wyndham Osceola IA

Super 8 by Wyndham Osceola IA

8/10 Good
"Comfortable beds, quiet and clean room. Breakfast room is way too tiny but the breakfast was decent for the price."
Jonathan 1-night trip
Posted 7 hours ago
Super 8 by Wyndham Osceola IA

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 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.