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Osceola County Holiday Rentals

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Top cities in Osceola County

A red barn with a colorful geometric quilt hanging on the front, a picnic table in front, and a silo in the background.
Vacation Rentals

Sibley

Sibley

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Osceola County holiday rentals

Living area

1. Quiet 1 bedroom in Milford with King Bed

Quiet 1 bedroom in Milford with King Bed
Milford
9.8 out of 10, Exceptional, (134 reviews)
"Very clean property, host were very friendly and attentive. Really enjoyed our stay here and will definitely be back."
United States
Angela H.
The price is AU$177
includes taxes & fees
1 Dec - 2 Dec
Quiet 1 bedroom in Milford with King Bed
A two-story house with a front porch, a garage, and a deck.

2. Located across the road of West Lake Okoboji. 8 beds. Room for parking trailers

Located across the road of West Lake Okoboji. 8 beds. Room for parking trailers
Okoboji
9.6 out of 10, Exceptional, (42 reviews)
"Nice stay"
United States
Jennifer C.
The price is AU$167
includes taxes & fees
16 Nov - 17 Nov
Located across the road of West Lake Okoboji. 8 beds. Room for parking trailers
A compact living space with a kitchenette, a dining area, and a seating area.

3. Nautical 1BR Loft Steps to East Okoboji Park

Nautical 1BR Loft Steps to East Okoboji Park
Spirit Lake
The price is AU$309
includes taxes & fees
15 Dec - 16 Dec
Nautical 1BR Loft Steps to East Okoboji Park
A living room with a grey sofa, a blue armchair, a floor lamp, and a patterned rug.

4. Quick 5-min drive to West Lake from Milford

Quick 5-min drive to West Lake from Milford
Milford
9.8 out of 10, Exceptional, (108 reviews)
"Great place to stay! Everything we needed plus a great bed. Parking for the boat and not far to state boat ramp"
United States
Jim S.
The price is AU$177
includes taxes & fees
1 Dec - 2 Dec
Quick 5-min drive to West Lake from Milford
A dining area with a wooden table, two chairs, a clock on the wall, and a window with curtains.

5. Just steps from The Green Space and Broadway Street. Fantastic Location for All the Fun!

Just steps from The Green Space and Broadway Street. Fantastic Location for All the Fun!
Arnolds Park
10.0 out of 10, Exceptional, (15 reviews)
"We had a great time at this air b n b for my bachelorette!! It was very spacious, close to the bars, and so cute for bachelorettes! I would stay here again and again"
United States
Kelsie H.
The price is AU$635
includes taxes & fees
16 Nov - 17 Nov
Just steps from The Green Space and Broadway Street. Fantastic Location for All the Fun!
A modern bathroom with a wooden vanity, a large mirror, and a dark wooden door.

6. 2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps.

2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps.
Arnolds Park
10.0 out of 10, Exceptional, (28 reviews)
"We enjoyed our stay, great location and host. Loved that there was parking for our boat and trailer as well as plug ins. Highly recommend."
United States
AMY T.
The price is AU$216
includes taxes & fees
16 Nov - 17 Nov
2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps.
A pool area with slides and a view of a building with balconies.

7. Bridges Bay Boji Lake-View Condo For Rent!!

Bridges Bay Boji Lake-View Condo For Rent!!
Arnolds Park
9.8 out of 10, Exceptional, (139 reviews)
"We had an amazing time, with great views. The condo had all the necessities and Janel was great to work with and very responsive. We hope to be back next year!"
United States
Deb E.
The price is AU$577
includes taxes & fees
16 Nov - 17 Nov
Bridges Bay Boji Lake-View Condo For Rent!!
A wooden play structure with a lookout tower and slides, surrounded by a blue pool area.

8. Cozy 2-bedroom suite with full kitchen, living room (couch, 2 chairs), dining table (2 stools), smart TV with cable. Perfect for short or long stays. This suite is one the 2nd level and requires guest to use stairs

Cozy 2-bedroom suite with full kitchen, living room (couch, 2 chairs), dining table (2 stools), smart TV with cable. Perfect for short or long stays. This suite is one the 2nd level and requires guest to use stairs
Arnolds Park
10.0 out of 10, Exceptional, (22 reviews)
"Just what we needed for our stay"
United States
Jeremiah M.
The price is AU$203
includes taxes & fees
22 Nov - 23 Nov
Cozy 2-bedroom suite with full kitchen, living room (couch, 2 chairs), dining table (2 stools), smart TV with cable. Perfect for short or long stays. This suite is one the 2nd level and requires guest to use stairs
A swimming pool with a slide, lounge chairs, and a small building.

9. Bridges Bay spacious, well-stocked kid-friendly home. 6 Pool Passes. Sleeps Ten

Bridges Bay spacious, well-stocked kid-friendly home. 6 Pool Passes. Sleeps Ten
Arnolds Park
10.0 out of 10, Exceptional, (162 reviews)
"Great experience, great location"
United States
Andy M.
The price is AU$574
includes taxes & fees
16 Nov - 17 Nov
Bridges Bay spacious, well-stocked kid-friendly home. 6 Pool Passes. Sleeps Ten
A beach with people sunbathing and swimming, boats docked in the water, and a water tower in the background.

10. 1400 sf 3 bedrooms in Arnolds Park-King bed<br>This suite is on the 3rd floor and does require a guest to use the steps.

1400 sf 3 bedrooms in Arnolds Park-King bed<br>This suite is on the 3rd floor and does require a guest to use the steps.
Arnolds Park
10.0 out of 10, Exceptional, (24 reviews)
"Very clean well cared for property, comfortable accommodations!"
United States
Cynthia M.
The price is AU$329
includes taxes & fees
18 Nov - 19 Nov
1400 sf 3 bedrooms in Arnolds Park-King bed<br>This suite is on the 3rd floor and does require a guest to use the steps.
A beach with people sunbathing and swimming, a dock with boats, and a water tower in the background.

11. 2 Bedroom along Highway 71<br>This suite is on the 2nd level and requires guests to use stairs.

2 Bedroom along Highway 71<br>This suite is on the 2nd level and requires guests to use stairs.
Arnolds Park
9.2 out of 10, Wonderful, (23 reviews)
"Great location. Host was accommodating and helpful. "
United States
Christine R.
The price is AU$298
includes taxes & fees
1 Dec - 2 Dec
2 Bedroom along Highway 71<br>This suite is on the 2nd level and requires guests to use stairs.
A modern living room with a dining area, a sofa, a TV, and a staircase leading to an outdoor area.

12. Suite for 11 Guests in Arnolds Park-4 Bedrooms 2 Bathrooms

Suite for 11 Guests in Arnolds Park-4 Bedrooms 2 Bathrooms
Arnolds Park
10.0 out of 10, Exceptional, (16 reviews)
"Always clean, wonderful place to stay while in Okoboji! Will continue to be repeat guests."
United States
Bethany R.
The price is AU$569
includes taxes & fees
16 Nov - 17 Nov
Suite for 11 Guests in Arnolds Park-4 Bedrooms 2 Bathrooms
A spacious living area with a sofa, coffee table, and a ceiling fan. There is a kitchen area with wooden cabinets and a dishwasher.

13. Beautiful Boji, Cabin #22

Beautiful Boji, Cabin #22
Arnolds Park
9.8 out of 10, Exceptional, (16 reviews)
"Just like a nice home. The kitchen being well-stocked with k cups was appreciated as we forgot to bring coffee. Had we known there was a stocked, private fishing pond out back we would have brought fishing rods! All in all, a really nice place."
United States
S. Mark
The price is AU$703
includes taxes & fees
1 Dec - 2 Dec
Beautiful Boji, Cabin #22
A wooden pier extending into calm water with a sunset in the background.

14. Cozy Condo by Boardwalk, Restaurants, Golf

Cozy Condo by Boardwalk, Restaurants, Golf
Arnolds Park
9.8 out of 10, Exceptional, (26 reviews)
"Great location. Host responds very quickly and is super friendly. Great place to host the family"
United States
Josiah C.
The price is AU$614
includes taxes & fees
16 Nov - 17 Nov
Cozy Condo by Boardwalk, Restaurants, Golf
A beach with people sunbathing and swimming, a dock with boats, and a water tower in the background.

15. Fantastic Location-Roof Top Patio (shared) and King Bed<br>This suite is on the 2nd level and requires guest to use stairs.

Fantastic Location-Roof Top Patio (shared) and King Bed<br>This suite is on the 2nd level and requires guest to use stairs.
Arnolds Park
10.0 out of 10, Exceptional, (37 reviews)
"Very nice and clean place. Great beds. I will stay there again."
United States
Patty F.
The price is AU$339
includes taxes & fees
1 Dec - 2 Dec
Fantastic Location-Roof Top Patio (shared) and King Bed<br>This suite is on the 2nd level and requires guest to use stairs.
A beach with people sunbathing and swimming, a dock with boats, and a water tower in the background.

16. The Stay Cabin is a part of the Stay Properties locations at 271 Hwy 71

The Stay Cabin is a part of the Stay Properties locations at 271 Hwy 71
Arnolds Park
10.0 out of 10, Exceptional, (16 reviews)
"The house was very nice and had plenty of space for our large family. Will stay here again!! "
United States
Carrie H.
The price is AU$606
includes taxes & fees
16 Nov - 17 Nov
The Stay Cabin is a part of the Stay Properties locations at 271 Hwy 71
A modern kitchen with stainless steel appliances, a bar area, and wooden flooring.

17. Charming remodeled 4-Bedroom home with fire pit

Charming remodeled 4-Bedroom home with fire pit
Spirit Lake
10.0 out of 10, Exceptional, (25 reviews)
"Great place, only down side was traffic noise as it is just off of the main road, but it was not a big deal at all."
United States
Becca D.
The price is AU$603
includes taxes & fees
16 Nov - 17 Nov
Charming remodeled 4-Bedroom home with fire pit
A pool area with multiple swimming pools, lounge chairs, and a children's play structure.

18. Bridges Bay Retreat - The Perfect Okoboji Getaway

Bridges Bay Retreat - The Perfect Okoboji Getaway
Arnolds Park
10.0 out of 10, Exceptional, (2 reviews)
"Great for the price, comfy and close to all the activities in Arnold’s park"
United States
Connor S.
The price is AU$578
includes taxes & fees
7 Dec - 8 Dec
Bridges Bay Retreat - The Perfect Okoboji Getaway
A room with a large window overlooking a lake, a wooden deck, and a boat.

19. Beautiful, quiet and fully renovated lakehouse on East Okoboji Lake.

Beautiful, quiet and fully renovated lakehouse on East Okoboji Lake.
Spirit Lake
9.6 out of 10, Exceptional, (9 reviews)
"enjoyed the lake view. relaxing"
United States
marilyn S.
The price is AU$687
includes taxes & fees
17 Nov - 18 Nov
Beautiful, quiet and fully renovated lakehouse on East Okoboji Lake.
A beach with people sunbathing and swimming, boats docked in the water, and a water tower in the background.

20. Fantastic Yard and Fun Location In Arnolds Park. Walk to Everything!

Fantastic Yard and Fun Location In Arnolds Park. Walk to Everything!
Arnolds Park
10.0 out of 10, Exceptional, (33 reviews)
"Very nice property. Friendly owners. Enjoyed our family time in Okoboji."
United States
Gwen
The price is AU$606
includes taxes & fees
18 Nov - 19 Nov
Fantastic Yard and Fun Location In Arnolds Park. Walk to Everything!
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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Find out more about Osceola County

Everything you need to know about Osceola County 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 County 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 County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Osceola County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osceola County. 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 County 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 County holiday rentals we have chosen for you start as low as AU$167 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Osceola County rentals

At Expedia, we put the best Osceola County 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 County 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 County 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 County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.