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

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
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
The Little Brick House - Walkable to the Square Dining & Shopping

Holiday Home in Winterset

10.0 out of 10, Exceptional, (3)
"This was an amazing house to rent. It was super cute and clean. It was walkable to the downtown. We stayed during the Bridges of Madison County festival and we were able to walk there. The host was great at communicating. I would stay here again and would recommend it to anyone visiting Winterset. "
United States
Melinda E.
The Little Brick House - Walkable to the Square Dining & Shopping
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.
Property grounds
Quiet Escape Near Rathbun Lake & Public Hunting Grounds

Holiday Home in Russell

10.0 out of 10, Exceptional, (1)
"It was a great experience "
United States
Mark N.
Quiet Escape Near Rathbun Lake & Public Hunting Grounds
Exterior
Cabin close to Lake Rathbun #3

Cabin in Melrose

10.0 out of 10, Exceptional, (7)
"It was the perfect place for a getaway with my wife"
United States
Michael C.
Cabin close to Lake Rathbun #3
Exterior
≋ The Cottage at Sun Valley Lake ≋

Cottage in Ellston

10.0 out of 10, Exceptional, (75)
"Absolutely beautiful place. "
United States
A P.
≋ The Cottage at Sun Valley Lake ≋
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 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
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
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
7 Dec - 8 Dec
The Gobbler Cabin - Hidden Acres Cabins
Private kitchen
blue sky cottage!!!!

Cottage in Bethany

10.0 out of 10, Exceptional, (4)
"As promoted, Blue Sky Cottage is a mid-1900s gas station renovated into a studio cottage. And what a delightful adaptation of the property - clean, cozy (perfect size for a couple), bright (lots of light in and reflected), well-furnished and stocked, and even a small patio for enjoying the outdoors. Also a great location for our forays to Pawnee Prairie and Dunn Ranch Prairie in search of birds (bobolinks quite prevalent in June). We enjoyed trying to figure out which parts of the building were...
United States
Paul H.
blue sky cottage!!!!
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
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.
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
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
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
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!
Interior
Cabin close to Lake Rathbun #5

Cabin in Melrose

9.6 out of 10, Exceptional, (7)
"Perfect for a quick stay while on a fishing trip. "
United States
Ryan D.
Cabin close to Lake Rathbun #5
Interior
Charming Winterset Vacation Rental w/ Yard & Patio

Cottage in Winterset

3.0 star property
10.0 out of 10, Exceptional, (1)
"We stayed here on a trip for the Knoxville Nationals. Went to the John Wayne Museum, seen the bridges. The house is a nice house, met many locals at the pharmacy-resturaunt in the square downtown, very friendly, ate at several other local spots, all good service and food. The area is quiet and the house in great shape, clean, had plenty of towels and comfortable beds. Would definitely recommend if you need a place in this area. "
United States
Tracy
Charming Winterset Vacation Rental w/ Yard & Patio
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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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.