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Osceola County Holiday Rentals

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Our top choices for Osceola County holiday rentals

Pool

1. Year Round Okoboji Vacation Rental at Bridges Bay Resort!

Year Round Okoboji Vacation Rental at Bridges Bay Resort!
Arnolds Park
9.8 out of 10, Exceptional, (136 reviews)
"Good location"
United States
Janean S.
The price is AU$1,072
includes taxes & fees
30 Aug - 31 Aug
Year Round Okoboji Vacation Rental at Bridges Bay Resort!
Exterior

2. BOHO Bungalow on the Pond

BOHO Bungalow on the Pond
Arnolds Park
10.0 out of 10, Exceptional, (13 reviews)
"Very clean. Comfortable beds. We enjoyed our stay!"
United States
Allie W.
BOHO Bungalow on the Pond
Children’s area

3. Cozy Okoboji Vacation Home At Bridges Bay Resort - backs to pool! #118

Cozy Okoboji Vacation Home At Bridges Bay Resort - backs to pool! #118
Arnolds Park
9.8 out of 10, Exceptional, (110 reviews)
"Love all of it had a blast at the pool"
United States
Hendy T.
The price is AU$1,159
includes taxes & fees
19 Aug - 20 Aug
Cozy Okoboji Vacation Home At Bridges Bay Resort - backs to pool! #118
Indoor pool, outdoor pool

4. Spacious & Luxurious Lakefront Bridge Bay Corner Condo. 6 daily waterpark passes

Spacious & Luxurious Lakefront Bridge Bay Corner Condo. 6 daily waterpark passes
Arnolds Park
10.0 out of 10, Exceptional, (33 reviews)
"We were visiting from Arizona and enjoyed our stay!"
United States
Michael G.
The price is AU$1,375
includes taxes & fees
29 Aug - 30 Aug
Spacious & Luxurious Lakefront Bridge Bay Corner Condo. 6 daily waterpark passes
Interior

5. 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, (23 reviews)
"I loved my stay at stay suites. Very clean, everything that was promised was there. No complaints. Will stay there again this summer if the availability is there."
United States
Chris
The price is AU$286
includes taxes & fees
17 Aug - 18 Aug
2 bedrooms with queen beds. <br>This suite is on the 2nd floor and does require a guest to use steps.
Smart TV, offices

6. 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, (99 reviews)
"Great little spot very cozy and would love to back in the future"
United States
Miguel
The price is AU$177
includes taxes & fees
17 Aug - 18 Aug
Quick 5-min drive to West Lake from Milford
Children’s area

7. 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, (26 reviews)
"Great location host and price. Place had everything we needed "
United States
Eric L.
The price is AU$438
includes taxes & fees
23 Aug - 24 Aug
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
Beach

8. 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, (23 reviews)
"Very clean, great location, quick responses from host. Great stay!"
United States
Janean S.
The price is AU$466
includes taxes & fees
26 Aug - 27 Aug
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.
Indoor pool, outdoor pool

9. Lake Front Condo on East Lake Okoboji in Bridges Bay Resort.

Lake Front Condo on East Lake Okoboji in Bridges Bay Resort.
ARNOLDS PARK
9.8 out of 10, Exceptional, (76 reviews)
"Great place with a beatiful view! The hosts were great communicators and the photos accurately depict the spaces."
United States
Candace J.
The price is AU$903
includes taxes & fees
13 Sept - 14 Sept
Lake Front Condo on East Lake Okoboji in Bridges Bay Resort.
Coffee/tea maker, fridge, microwave, oven

10. Charming remodeled 4-Bedroom home with fire pit

Charming remodeled 4-Bedroom home with fire pit
Spirit Lake
10.0 out of 10, Exceptional, (23 reviews)
"Perfect size and location for a family ice fishing trip. Cozy and comfortable, all the amenities you would need, and close to lots of dining options. "
United States
Clint C.
The price is AU$579
includes taxes & fees
17 Aug - 18 Aug
Charming remodeled 4-Bedroom home with fire pit
TV

11. West Lake Okoboji Scout Cottage

West Lake Okoboji Scout Cottage
Arnolds Park
9.8 out of 10, Exceptional, (12 reviews)
"Nice clean cottage style. perfect for a couples stay. location is perfect for walking distance to many attractions including arnold's park and much more!"
United States
Stephanie K.
The price is AU$657
includes taxes & fees
17 Aug - 18 Aug
West Lake Okoboji Scout Cottage
Beach

12. 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, (13 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$1,019
includes taxes & fees
17 Aug - 18 Aug
The Stay Cabin is a part of the Stay Properties locations at 271 Hwy 71
Coffee/tea maker, fridge, microwave, oven

13. Okoboji Oasis at the Lake in Arnolds Park

Okoboji Oasis at the Lake in Arnolds Park
Arnolds Park
9.6 out of 10, Exceptional, (5 reviews)
"Great location. Very close to Arnolds Park"
United States
Tom D.
The price is AU$1,327
includes taxes & fees
20 Aug - 21 Aug
Okoboji Oasis at the Lake in Arnolds Park
Property grounds

14. Lakefront Luxury! Spacious corner condo, wrap around deck. 6 BB waterpark passes

Lakefront Luxury! Spacious corner condo, wrap around deck. 6 BB waterpark passes
Arnolds Park
10.0 out of 10, Exceptional, (116 reviews)
"The condo was wonderful. Well-stocked/equipped, clean, tastefully decorated, and the beautiful water view we were looking for. We will definitely return. "
United States
Pat H.
The price is AU$768
includes taxes & fees
15 Sept - 16 Sept
Lakefront Luxury! Spacious corner condo, wrap around deck. 6 BB waterpark passes
Interior

15. Direct Lakeside View, 3 Bed, 2 Bath Condo at Bridges Bay

Direct Lakeside View, 3 Bed, 2 Bath Condo at Bridges Bay
Arnolds Park
9.8 out of 10, Exceptional, (80 reviews)
"Beautiful lake view and good location."
United States
Nancy C.
The price is AU$801
includes taxes & fees
14 Sept - 15 Sept
Direct Lakeside View, 3 Bed, 2 Bath Condo at Bridges Bay
Interior

16. Poolside Retreat at Bridges Bay

Poolside Retreat at Bridges Bay
Arnolds Park
10.0 out of 10, Exceptional, (3 reviews)
"Very nice house. Everything was clean and well stocked. "
United States
Bill A.
The price is AU$573
includes taxes & fees
23 Aug - 24 Aug
Poolside Retreat at Bridges Bay
Terrace/patio

17. Premier Location! Lake View!

Premier Location! Lake View!
Arnolds Park
10.0 out of 10, Exceptional, (11 reviews)
"Really enjoyed the place. It is within walking distant to all shops and Arnolds Park. "
United States
Jeff Z.
The price is AU$935
includes taxes & fees
24 Aug - 25 Aug
Premier Location! Lake View!
Exterior

18. Bring ALL of your family and friends to stay at the Central Stay Cation in Arnolds Park!

Bring ALL of your family and friends to stay at the Central Stay Cation in Arnolds Park!
Arnolds Park
10.0 out of 10, Exceptional, (133 reviews)
"We love hosting team retreats in this space! It’s always clean, no toxic plugin air fresheners & an amazing location!"
United States
AmandaW
The price is AU$1,488
includes taxes & fees
8 Sept - 9 Sept
Bring ALL of your family and friends to stay at the Central Stay Cation in Arnolds Park!
Terrace/patio

19. The Canal Cottages off West Lake Okoboji

The Canal Cottages off West Lake Okoboji
Milford
8.8 out of 10, Excellent, (3 reviews)
"Great little cottage"
United States
Ben P.
The price is AU$998
includes taxes & fees
11 Sept - 12 Sept
The Canal Cottages off West Lake Okoboji
Indoor pool

20. Beachy Keen at Bridges Bay Resort

Beachy Keen at Bridges Bay Resort
Arnolds Park
10.0 out of 10, Exceptional, (3 reviews)
"The overall condo was clean and spacious! We had a wonderful stay! The condo faces the water and there was easy access for my grandkids to fish in the morning. There were yard games for us to use so the kids loved that! Plenty of linens and blankets as it got pretty chilly Labor Day weekend. There were plenty of kitchen pans to make breakfast in the morning and the grill was great to grill food for lunch! Great Condo! We will be back!"
United States
Sueann F.
The price is AU$496
includes taxes & fees
27 Aug - 28 Aug
Beachy Keen at Bridges Bay Resort
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

Spencer Inn and Suites

Spencer Inn and Suites

10/10 Excellent
"The staff was very welcoming. The hotel is older, but looked well maintained. The beds were comfortable and the shower was so perfectly wonderful... you didn't want to get out! 😊"
Jodi 1-night trip
Posted 13 hours ago
Spencer Inn and Suites

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$560 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.