Osceola County Holiday Rentals

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Our top choices for Osceola County holiday rentals

10.0 out of 10, Exceptional, (106)
"Loved our stay here -remote quiet getaway! Loved the jukebox pinball and Pac-Man game and the jet tub! "
United States
Shannon
The price is NZ$258
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy cabin in the woods
9.6 out of 10, Exceptional, (18)
"Fun A-frame on Muskegon River. Plenty of great activities like kayaking, grilling, board games, and bonfire'n! Will definitely be returning. "
United States
Connor D.
The price is NZ$504
includes taxes & fees
4 Jan - 5 Jan 2026
A-Frame | Hot Tub, Fireplace, River, Kayaks &Tubes
9.4 out of 10, Exceptional, (13)
"Beautiful scenery. Quiet and peaceful. Exactly what we were looking for. "
United States
Samantha H.
The price is NZ$597
includes taxes & fees
6 Jan - 7 Jan 2026
Riverfront | Hot Tub, Fireplace, Kayaks & Tubes
9.2 out of 10, Wonderful, (7)
"Cabin was well appointed and clean upon arrival. Enjoyed the serenity but close enough to town for shopping or food. Would totally rent again."
United States
Scott
The price is NZ$504
includes taxes & fees
5 Jan - 6 Jan 2026
Secluded | Sauna, Fire Pit & 20 Acres of Trails
10.0 out of 10, Exceptional, (12)
"Property was clean, location was beautiful and the host was great to communicate with."
United States
Nicholas B.
The price is NZ$651
includes taxes & fees
7 Jan - 8 Jan 2026
Riverfront | Hot Tub, Fireplace, Kayaks & Tubes
9.6 out of 10, Exceptional, (23)
"I really enjoyed my stay it was very peaceful and calming at this location I love being inside the woods and enjoying the nature outside of my stay. Well worth it and vary safe place to bring your family and enjoying your time."
United States
Tony V.
The price is NZ$607
includes taxes & fees
27 Jan - 28 Jan 2026
Luxe Log Chalet | Sauna, River, Fire, Kayaks/Tubes
9.0 out of 10, Wonderful, (10)
"The moment we pulled up to the drive way I knew it was going to be an amazing stay. From the cottage feel to the abundance of fun things to do (kayaking, fishing, grilling, outdoor / indoor games, and so much more!) there was no shortage of family memories to build. So much so this place would be good for a multitude of stays: from romantic getaways, family (infant and kid friendly) excursions, and even just a fun adventure with friends, the riverside retreat stay was a 10/5 in my book. AC in...
United States
Goku C.
The price is NZ$548
includes taxes & fees
4 Jan - 5 Jan 2026
Riverside Retreat | Sauna, Fireplace, Kayaks/Tubes
8.6 out of 10, Excellent, (7)
"Lovely spot to get in touch with nature :)"
United States
Patrick S.
The price is NZ$617
includes taxes & fees
7 Jan - 8 Jan 2026
Secluded Riverfront Cottage | Sauna, Fire & Kayaks
9.8 out of 10, Exceptional, (19)
"Lake view, pet friendly, cleanliness, location and great communication with host. Beautiful home with amenities included if needed to relax and enjoy yourself to a nice getaway. "
United States
Jennie D.
OPEN! LAKE CABIN Stocked, king bed, Wifi,Games, Smart TVs Washer Dryer, Pet
10.0 out of 10, Exceptional, (2)
"Overall great place to stay. Clean, comfortable bed, had everything we needed. "
United States
Tori R.
The price is NZ$241
includes taxes & fees
11 Jan - 12 Jan 2026
Tiny Excursion Cabin 5 - Michigan Moonlight

Holiday Home in Harrison

The Lodge at Tiny Excursion Cabins
10.0 out of 10, Exceptional, (3)
"Wonderful little place for a weekend stay! "
United States
Shannon S.
The price is NZ$305
includes taxes & fees
5 Jan - 6 Jan 2026
The Lodge at Tiny Excursion Cabins
10.0 out of 10, Exceptional, (14)
"Great spot on the lakeside. Totally recommend this place if you’re in the area and in need of small lakeside accommodations. "
United States
abby S.
The price is NZ$343
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy lakefront cabin with fireplace, private beach, 2 firepits. Open year round!

Holiday Home in Chippewa Lake

Chippewa Lake House
3.0 star property
Chippewa Lake House
2.0 star property
10.0 out of 10, Exceptional, (29)
"Warm, welcoming, everything that you could think of was provided. Very cozy, will be back! "
United States
David J.
The price is NZ$412
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy loft retreat with lake views and access.
9.6 out of 10, Exceptional, (15)
"This was a great place for our family to gather and visit."
United States
Leslie F.
The price is NZ$801
includes taxes & fees
13 Jan - 14 Jan 2026
Amazing lake views for the perfect family getaway at the Lake Thirteen Retreat!
8.0 out of 10, Very good, (1)
"Lot of the houses around it were dumps But it was a nice place"
United States
Jay
The price is NZ$456
includes taxes & fees
4 Jan - 5 Jan 2026
Bear Lake | Kayaks, Firepit, Lake Access, Beach
10.0 out of 10, Exceptional, (3)
"Clean, great location and perfect for families. A little cozy cabin in the woods with great access to downtown and the lake. Nice kitchen and comfortable beds. Highly recommended this stay. 😁"
United States
Kaity M.
The price is NZ$329
includes taxes & fees
11 Jan - 12 Jan 2026
Cottages #7 Tree Tops, 2 Bedroom Cottage

Cabin in Big Rapids

Cozy Little Cabin #4
2.0 star property
9.4 out of 10, Exceptional, (22)
"Very nice little place, just what I needed "
United States
Dusty
The price is NZ$296
includes taxes & fees
11 Jan - 12 Jan 2026
Cozy Little Cabin #4

Holiday Home in Cadillac

Stone Ledge Lake Getaway
3.5 star property
10.0 out of 10, Exceptional, (3)
"Very well stocked and spacious - just a really good fit for our family!"
Canada
Denise
Stone Ledge Lake Getaway
9.8 out of 10, Exceptional, (20)
"Great location, house was clean and comfortable. Would stay again! "
United States
Brei H.
The price is NZ$814
includes taxes & fees
15 Jan - 16 Jan 2026
Charming 4-bedroom house with WiFi and AC in peaceful Lake City. Sleeps 12.
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

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 favorite 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 depends 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 selected for you start as low as NZ$444 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. 

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