Osceola Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Osceola

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

Apartment in Creston

10.0 out of 10, Exceptional, (5)
"Well maintained, quiet. Very comfortable and affordable "
United States
Sherry D.
The price is HK$770
HK$1,482 total
includes taxes & fees
3 Jan - 4 Jan 2026
2-bedroom apartment close to uptown Creston with WiFi and off street parking.
Exterior
Charming 3-bedroom house in Decatur City, Minutes from Little River Lake.

Holiday Home in Decatur City

2.0 star property
10.0 out of 10, Exceptional, (15)
"This place is perfect for our short fishing trip. Very clean, great location. Would stay again."
United States
MIKE L.
The price is HK$1,012
HK$1,569 total
includes taxes & fees
9 Dec - 10 Dec
Charming 3-bedroom house in Decatur City, Minutes from Little River Lake.
Fridge, microwave, oven, stovetop
Adair Hideaway : Quiet Neighborhood - Fenced Yard - Garage Parking

Holiday Home in Creston

The price is HK$973
HK$1,700 total
includes taxes & fees
10 Dec - 11 Dec
Adair Hideaway : Quiet Neighborhood - Fenced Yard - Garage Parking
Private kitchen
Cozy pond house nestled in nature waiting for you to enjoy

Cabin in Osceola

2.0 star property
The price is HK$817
HK$1,307 total
includes taxes & fees
17 Dec - 18 Dec
Cozy pond house nestled in nature waiting for you to enjoy
Property grounds
Serenity Heights - Peaceful Country Acres with beautiful view in every direction

Holiday Home in Osceola

10.0 out of 10, Exceptional, (83)
"Beautiful property with great patios. "
United States
Chris S.
The price is HK$1,751
HK$3,023 total
includes taxes & fees
3 Jan - 4 Jan 2026
Serenity Heights - Peaceful Country Acres with beautiful view in every direction
WiFi, bed sheets
The Gobbler Cabin - Hidden Acres Cabins

Cabin in Bethany

10.0 out of 10, Exceptional, (5)
"Great stay. Clean and nice property. "
United States
JA W.
The price is HK$1,089
HK$1,331 total
includes taxes & fees
10 Dec - 11 Dec
The Gobbler Cabin - Hidden Acres Cabins
Fridge, microwave, oven, stovetop
The Hen House Country Living with Farm Life Appeal Indianola, IA

Holiday Home in Indianola

10.0 out of 10, Exceptional, (7)
"Our host was amazing. Went above to make sure we had a great stay. Very personable..We both enjoyed visiting with her and learning more about the area. We will definitely return to the Hen House"
United States
Madonna
The price is HK$1,051
HK$1,487 total
includes taxes & fees
14 Dec - 15 Dec
The Hen House Country Living with Farm Life Appeal Indianola, IA
Microwave, oven, stovetop, dishwasher
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Holiday Home in Winterset

10.0 out of 10, Exceptional, (4)
"The house was absolutely gorgeous! It was very comfortable and had everything we needed. I would most definitely stay here again!"
United States
Heather G.
The price is HK$953
HK$2,733 total
includes taxes & fees
15 Dec - 16 Dec
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
Interior
Cabin close to Lake Rathbun #1

Cabin in Melrose

10.0 out of 10, Exceptional, (9)
"Loved the stay, Awesome location and great experience. The management was awesome, I would likely rent again."
United States
Jeremy A.
The price is HK$1,167
HK$1,871 total
includes taxes & fees
14 Dec - 15 Dec
Cabin close to Lake Rathbun #1
Fridge, microwave, oven, stovetop
The Bear Cabin - Hidden Acres Cabins

Cabin in Bethany

10.0 out of 10, Exceptional, (1)
"Clean accommodations, comfy beds, and beautiful location. A couple questions I had for the owner were answered immediately. We will definitely book here next time we come through this area!"
United States
Melody Z.
The price is HK$1,556
HK$1,881 total
includes taxes & fees
6 Dec - 7 Dec
The Bear Cabin - Hidden Acres Cabins
TV, fireplace
The Elk Cabin - Hidden Acres Cabins

Cabin in Bethany

10.0 out of 10, Exceptional, (1)
"Yes and yes, everything was good. However, it was not Nove 12-19,, , it was Nov 13-20"
United States
joseph h.
The price is HK$1,245
HK$1,506 total
includes taxes & fees
11 Dec - 12 Dec
The Elk Cabin - Hidden Acres Cabins
Fridge, microwave, oven, stovetop
• Lively Cottage 2 King Beds 4 Bed 2 Bath •

Holiday Home in Indianola

9.4 out of 10, Exceptional, (18)
"This is our 4th stay at the property. It's just as advertised and perfect for our needs. The neighborhood is very quiet and perfect for walking our dog. This time we extended our stay by one day at the start. I messaged the host and he made the process very easy."
United States
Mary W.
The price is HK$807
HK$1,924 total
includes taxes & fees
16 Dec - 17 Dec
• Lively Cottage 2 King Beds 4 Bed 2 Bath •
Interior
Cabin close to Lake Rathbun #2

Cabin in Melrose

9.8 out of 10, Exceptional, (16)
"The area was secluded and quiet and the cabin was clean and well maintained. We enjoyed our stay and the fire pit out back. "
United States
Melissa B.
The price is HK$1,167
HK$1,871 total
includes taxes & fees
7 Dec - 8 Dec
Cabin close to Lake Rathbun #2
Property grounds
Beautiful Rustic Barn just waiting for you to kick back and relax.

Holiday Home in NEW VIRGINIA

10.0 out of 10, Exceptional, (403)
"Needed a a quick getaway....it was perfect "
United States
Lee F.
The price is HK$895
HK$1,479 total
includes taxes & fees
10 Dec - 11 Dec
Beautiful Rustic Barn just waiting for you to kick back and relax.
Fridge, microwave, oven, stovetop
The Caribou Cabin - Hidden Acres Cabins

Cabin in Bethany

10.0 out of 10, Exceptional, (1)
"The property manager was prompt and courteous. The property was clean and comfortable."
United States
michelle c.
The price is HK$1,556
HK$1,881 total
includes taxes & fees
6 Dec - 7 Dec
The Caribou Cabin - Hidden Acres Cabins
Interior
Looking for a getaway? This property is perfect for your vacation!

Cabin in Weldon

9.8 out of 10, Exceptional, (56)
"Our 4th or 5th stay at the Weldon farm. We love the peace and quiet and will always return here for family visits."
United States
Lisa W.
The price is HK$1,051
HK$1,961 total
includes taxes & fees
17 Dec - 18 Dec
Looking for a getaway? This property is perfect for your vacation!
Iron/ironing board, WiFi, bed sheets
Corydon Family Home 3-Bedroom

Holiday Home in Corydon

2.0 star property
The price is HK$1,556
HK$3,416 total
includes taxes & fees
11 Dec - 12 Dec
Corydon Family Home 3-Bedroom
Interior
Royal Realm

Holiday Home in Corydon

The price is HK$1,012
HK$1,226 total
includes taxes & fees
6 Dec - 7 Dec
Royal Realm
1 bedroom, free WiFi, bed sheets, wheelchair access
Charming Highland

Holiday Home in Corydon

The price is HK$1,012
HK$1,226 total
includes taxes & fees
6 Dec - 7 Dec
Charming Highland
1 bedroom, free WiFi, bed sheets, wheelchair access
Timeless Prestine

Holiday Home in Corydon

The price is HK$1,012
HK$1,226 total
includes taxes & fees
7 Dec - 8 Dec
Timeless Prestine
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

Lakeside Hotel Casino

Lakeside Hotel Casino

10/10 Excellent
"We had a great time "
Todd 1-night trip
Posted 2 days ago
Lakeside Hotel Casino

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:

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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.