Osceola Holiday Rentals

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Osceola holiday rentals

Exterior

Cabin in Osceola

Cozy pond house nestled in nature waiting for you to enjoy
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"This was our first stay at a place like this. It was an incredibly relaxing stay. Host was very responsive even before our stay with any questions. I plan to come back! "
United States
Kristy A.
The price is HK$819
HK$1,310 total
includes taxes & fees
23 Jan - 24 Jan
Cozy pond house nestled in nature waiting for you to enjoy
Interior

Apartment in Creston

2-bedroom apartment close to uptown Creston with WiFi and off street parking.
10.0 out of 10, Exceptional, (5 reviews)
"Quite nice little place to stay"
United States
Mark P.
The price is HK$772
HK$1,493 total
includes taxes & fees
28 Jan - 29 Jan
2-bedroom apartment close to uptown Creston with WiFi and off street parking.
Fridge, microwave, oven, stovetop

Holiday Home in Decatur City

Charming 3-bedroom house in Decatur City, Minutes from Little River Lake.
2.0 star property
10.0 out of 10, Exceptional, (15 reviews)
"This place is perfect for our short fishing trip. Very clean, great location. Would stay again."
United States
MIKE L.
The price is HK$1,014
HK$1,555 total
includes taxes & fees
24 Jan - 25 Jan
Charming 3-bedroom house in Decatur City, Minutes from Little River Lake.
2 bedrooms, free WiFi, bed sheets

Holiday Home in Creston

Adair Hideaway : Quiet Neighborhood - Fenced Yard - Garage Parking
The price is HK$1,146
HK$1,930 total
includes taxes & fees
26 Jan - 27 Jan
Adair Hideaway : Quiet Neighborhood - Fenced Yard - Garage Parking
3 bedrooms, desk, iron/ironing board, travel cot

Holiday Home in Osceola

Serenity Heights - Peaceful Country Acres with beautiful view in every direction
10.0 out of 10, Exceptional, (84 reviews)
"Beautiful location in the country. Great place to see sunsets and sunrises. Scenery is fantastic. Convenient to stores, places to shop, and activities."
United States
Karen I.
The price is HK$1,228
HK$2,412 total
includes taxes & fees
3 Feb - 4 Feb
Serenity Heights - Peaceful Country Acres with beautiful view in every direction
Smart TV

Holiday Home in Indianola

• Lively Cottage 2 King Beds 4 Bed 2 Bath •
9.4 out of 10, Exceptional, (18 reviews)
"Had a great stay, will come back!"
United States
Spring A.
The price is HK$780
HK$1,843 total
includes taxes & fees
25 Jan - 26 Jan
• Lively Cottage 2 King Beds 4 Bed 2 Bath •
Property grounds

Holiday Home in NEW VIRGINIA

Beautiful Rustic Barn just waiting for you to kick back and relax.
10.0 out of 10, Exceptional, (406 reviews)
"Amazing property "
United States
Anonymous traveller
The price is HK$897
HK$1,474 total
includes taxes & fees
22 Jan - 23 Jan
Beautiful Rustic Barn just waiting for you to kick back and relax.
Outdoor dining

Holiday Home in Winterset

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
10.0 out of 10, Exceptional, (5 reviews)
"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$834
HK$2,584 total
includes taxes & fees
26 Jan - 27 Jan
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
Fridge, microwave, oven, stovetop

Holiday Home in Indianola

The Hen House Country Living with Farm Life Appeal Indianola, IA
10.0 out of 10, Exceptional, (9 reviews)
"Lori and Les make you feel right at home. They go above and beyond to ensure you have everything you could need and more. The farm is so peaceful and watching the animals is entertaining."
United States
Valerie
The price is HK$1,053
HK$1,474 total
includes taxes & fees
22 Jan - 23 Jan
The Hen House Country Living with Farm Life Appeal Indianola, IA
Interior

Holiday Home in Clearfield

Pleasant 3-bedroom bungalow with AC in charming Clearfield
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Outstanding host and amenities."
United States
Jeff T.
The price is HK$530
HK$876 total
includes taxes & fees
1 Feb - 2 Feb
Pleasant 3-bedroom bungalow with AC in charming Clearfield
Interior

Cabin in Melrose

Cabin close to Lake Rathbun #2
9.8 out of 10, Exceptional, (16 reviews)
"Nice cabin! Great for two of us with 2 dogs"
United States
Jeremy S.
The price is HK$1,170
HK$1,875 total
includes taxes & fees
24 Jan - 25 Jan
Cabin close to Lake Rathbun #2
Outdoor dining

Cabin in Weldon

Looking for a getaway? This property is perfect for your vacation!
9.6 out of 10, Exceptional, (58 reviews)
"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$1,053
HK$1,965 total
includes taxes & fees
23 Jan - 24 Jan
Looking for a getaway? This property is perfect for your vacation!
Fridge, microwave, oven, stovetop

Cabin in Bethany

The Bear Cabin - Hidden Acres Cabins
10.0 out of 10, Exceptional, (2 reviews)
"The place was really clean and had everything we needed. We would definitely stay again!"
United Kingdom
Misty M.
The price is HK$1,559
HK$1,884 total
includes taxes & fees
24 Jan - 25 Jan
The Bear Cabin - Hidden Acres Cabins
1 bedroom, free WiFi, bed sheets, wheelchair access

Holiday Home in Corydon

Timeless Prestine
The price is HK$1,013
HK$1,228 total
includes taxes & fees
22 Jan - 23 Jan
Timeless Prestine
1 bedroom, free WiFi, bed sheets, wheelchair access

Holiday Home in Corydon

Boho Bungalow
The price is HK$1,013
HK$1,228 total
includes taxes & fees
30 Jan - 31 Jan
Boho Bungalow
Interior

Holiday Home in Corydon

Corydon Family Home 3-Bedroom
2.0 star property
The price is HK$1,559
HK$3,422 total
includes taxes & fees
22 Jan - 23 Jan
Corydon Family Home 3-Bedroom
1 bedroom, free WiFi, bed sheets, wheelchair access

Holiday Home in Corydon

Charming Highland
The price is HK$1,013
HK$1,228 total
includes taxes & fees
22 Jan - 23 Jan
Charming Highland
Interior

Holiday Home in Corydon

Royal Realm
The price is HK$1,013
HK$1,228 total
includes taxes & fees
22 Jan - 23 Jan
Royal Realm
Interior

Cabin in Melrose

Cabin close to Lake Rathbun #1
10.0 out of 10, Exceptional, (9 reviews)
"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$1,170
HK$1,875 total
includes taxes & fees
24 Jan - 25 Jan
Cabin close to Lake Rathbun #1
TV, fireplace

Cabin in Bethany

The Caribou Cabin - Hidden Acres Cabins
10.0 out of 10, Exceptional, (1 review)
"The property manager was prompt and courteous. The property was clean and comfortable."
United States
michelle c.
The price is HK$1,559
HK$1,884 total
includes taxes & fees
24 Jan - 25 Jan
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

Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA

10/10 Excellent
"Clean rooms. Friendly staff and easy to find "
Tracey 1-night trip
Posted 3 days ago
Cobblestone Inn & Suites - Winterset, IA

Find out more about Osceola

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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 Revelton Distilling Company 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.