A large river winding through a green landscape with trees and fields.

Osceola Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 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 AU$254
includes taxes & fees
24 Sept - 25 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 AU$266
includes taxes & fees
27 Sept - 28 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 AU$269
includes taxes & fees
28 Sept - 29 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 AU$325
includes taxes & fees
24 Sept - 25 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 AU$243
includes taxes & fees
24 Sept - 25 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)
"Great quiet atmosphere. Nice place to relax."
United States
Gary S.
The price is AU$195
includes taxes & fees
5 Oct - 6 Oct
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 AU$292
includes taxes & fees
5 Oct - 6 Oct
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 AU$270
includes taxes & fees
29 Sept - 30 Sept
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.

9. 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$448
includes taxes & fees
28 Sept - 29 Sept
Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset
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
9.8 out of 10, Exceptional, (11 reviews)
"It was a great stay!"
United States
Dustin F.
The price is AU$173
includes taxes & fees
28 Sept - 29 Sept
Pleasant 3-bedroom bungalow with AC in charming Clearfield
A modern hotel room with a large bed, a wooden headboard, a flat-screen TV, a bedside table, and a mirror.

11. 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$224
includes taxes & fees
24 Sept - 25 Sept
Charming Highland
A log cabin room with a bed, a fireplace, a television, and a window with blinds.

12. The Gobbler Cabin - Hidden Acres Cabins

The Gobbler Cabin - Hidden Acres Cabins
Bethany
9.2 out of 10, Wonderful, (12 reviews)
"Great cabin! Very clean, loved the pond with ducks! Thank you!"
United States
Brandee M.
The price is AU$243
includes taxes & fees
24 Sept - 25 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.

13. 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$334
includes taxes & fees
26 Sept - 27 Sept
Cabin close to Lake Rathbun #2
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
10.0 out of 10, Exceptional, (1 review)
"The home was wonderful, the surroundings even better. It is such a peaceful location. Just sitting in the porch in the early morning listening to the birds and frogs makes the stay worthwhile. The owners are very helpful, friendly, and communicative. We enjoyed the amenities such as the outdoor patio, firepit, tvs, and griddle to name a few. And to think they have plans to continue to make improvements! We completely enjoyed our time there and truly hope we can go there again."
United States
Shawn L.
The price is AU$399
includes taxes & fees
24 Sept - 25 Sept
Yopp's Hideaway, farm stay near Lake Icaria on 26 acres, w/pond & animal visits.
A wooden cabin with a porch, large windows, and a stone pathway leading to the entrance.

15. Secluded Cabin

Secluded Cabin
Princeton
The price is AU$623
includes taxes & fees
30 Sept - 1 Oct
Secluded Cabin
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 #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 AU$334
includes taxes & fees
24 Sept - 25 Sept
Cabin close to Lake Rathbun #4
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 #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$334
includes taxes & fees
24 Sept - 25 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.

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$334
includes taxes & fees
26 Sept - 27 Sept
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 #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$334
includes taxes & fees
26 Sept - 27 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.

20. 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 AU$275
includes taxes & fees
24 Sept - 25 Sept
The Elk 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

Lakeside Hotel Casino, a Travelodge by Wyndham

Lakeside Hotel Casino, a Travelodge by Wyndham

10/10 Excellent
"Clean room"
Joyce 1-night trip
Posted 1 hour ago
Lakeside Hotel Casino, a Travelodge by Wyndham

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$195 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.