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Osceola County Vacation Rentals

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Our top choices for Osceola County vacation rentals

A staircase with a patterned carpet and a wall with a black and white abstract design.

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 CA $84
CA $169 total
includes taxes & fees
Dec 12 - Dec 13
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 CA $128
CA $160 total
includes taxes & fees
Nov 15 - Nov 16
Located across the road of West Lake Okoboji. 8 beds. Room for parking trailers
A two-story brick building with a central entrance, a staircase, and a small garden area with plants.

3. Nautical 1BR Loft Steps to East Okoboji Park

Nautical 1BR Loft Steps to East Okoboji Park
Spirit Lake
The price is CA $136
CA $392 total
includes taxes & fees
Nov 14 - Nov 15
Nautical 1BR Loft Steps to East Okoboji Park
A green door with a keypad lock, a 'B' above it, and a 'stay safe' sign on the wall.

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 CA $84
CA $169 total
includes taxes & fees
Dec 12 - Dec 13
Quick 5-min drive to West Lake from Milford
A covered outdoor area with stone pillars and a wooden roof, featuring tables and chairs, likely for dining or events.

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 CA $158
CA $626 total
includes taxes & fees
Nov 14 - Nov 15
Just steps from The Green Space and Broadway Street. Fantastic Location for All the Fun!
A staircase with a sign that reads 'Welcome to Stay Suites.'

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 CA $89
CA $207 total
includes taxes & fees
Nov 15 - Nov 16
2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps.
A multi-story building with balconies overlooking a body of water.

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 CA $214
CA $575 total
includes taxes & fees
Nov 14 - Nov 15
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 CA $110
CA $195 total
includes taxes & fees
Nov 22 - Nov 23
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 covered outdoor area with a table and chairs, a grill, and a view of surrounding buildings.

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 CA $99
CA $572 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $94
CA $304 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $158
CA $289 total
includes taxes & fees
Dec 1 - Dec 2
2 Bedroom along Highway 71<br>This suite is on the 2nd level and requires guests to use stairs.
A modern kitchen with a dining area, a bar, and a seating area with a couch and a chair.

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 CA $206
CA $535 total
includes taxes & fees
Nov 25 - Nov 26
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)
"The cabin was wonderful and well acquainted our large family. The walk to the pool was fast and easy. The hosts were very helpful."
United States
Tonya S.
The price is CA $285
CA $697 total
includes taxes & fees
Dec 1 - Dec 2
Beautiful Boji, Cabin #22
A wooden pier extending into calm waters with boats docked at the end.

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 CA $212
CA $605 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $142
CA $327 total
includes taxes & fees
Dec 1 - Dec 2
Fantastic Location-Roof Top Patio (shared) and King Bed<br>This suite is on the 2nd level and requires guest to use stairs.
A spacious living room with a large sofa, a smaller couch, a coffee table, and a TV mounted on the wall.

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 CA $206
CA $598 total
includes taxes & fees
Nov 14 - Nov 15
The Stay Cabin is a part of the Stay Properties locations at 271 Hwy 71
A wooden deck with wicker furniture and a small table.

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 CA $354
CA $594 total
includes taxes & fees
Nov 16 - Nov 17
Charming remodeled 4-Bedroom home with fire pit
An outdoor patio with a round table and chairs, a small pond, and a view of houses across the water.

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 CA $184
CA $570 total
includes taxes & fees
Dec 7 - Dec 8
Bridges Bay Retreat - The Perfect Okoboji Getaway
A view of a lake with two Adirondack chairs and a fishing rod leaning against a tree.

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 CA $321
CA $695 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $206
CA $598 total
includes taxes & fees
Nov 18 - Nov 19
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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Top Osceola County Hotel Reviews

Cobblestone Inn & Suites - Sheldon

Cobblestone Inn & Suites - Sheldon

8/10 Good
"We checked in for a one night stay. We had a jacuzzi room, it was a good room. The bed was very firm.....so good of that's what you like. The place was modern and clean. No strange smells or dirty areas. The breakfast was a regular hotel breakfast. Not bad. The check in was quick and easy, the staff was nice. The drink choices in the cooler were not great. No regular sodas. Overall not bad, we would stay again."
Heather 1-night trip
Posted 1 day ago
Cobblestone Inn & Suites - Sheldon

Find out more about Osceola County

Everything you need to know about Osceola County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osceola County vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Osceola County vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osceola County vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osceola County vacation rentals we have selected for you start as low as CA $160 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 vacation 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 vacation.

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.