An aerial view of a coastal city with high-rise buildings, a curved waterfront promenade, and a beach.

Osceola County Vacation Rentals

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Our top choices for Osceola County vacation rentals

A modern house with a wooden deck, outdoor furniture, and a large umbrella.

1. Modern Hersey Tiny Home w/ Private Hot Tub!

Modern Hersey Tiny Home w/ Private Hot Tub!
3.0 star property
Hersey
The price is CA $224
CA $376 total
includes taxes & fees
Oct 25 - Oct 26
Modern Hersey Tiny Home w/ Private Hot Tub!
A wooden cabin with a snow-covered porch and a small porch area.

2. Quiet Woodland Escape Secluded 3BR Cabin on 30 Acres

Quiet Woodland Escape Secluded 3BR Cabin on 30 Acres
Sears
10.0 out of 10, Exceptional, (11 reviews)
"Absolutely a beautiful getaway! The host was so easy to work with & communicated great with me the entire stay. "
United States
Zoe M.
The price is CA $249
CA $407 total
includes taxes & fees
Oct 12 - Oct 13
Quiet Woodland Escape Secluded 3BR Cabin on 30 Acres
A cabin interior with a wooden floor, large windows, a couch, and a door leading outside.

3. Riverfront Retreat | Fire, Sunroom, Kayaks, Tubes

Riverfront Retreat | Fire, Sunroom, Kayaks, Tubes
Sears
10.0 out of 10, Exceptional, (1 review)
"We had such a great time here for our anniversary! We took the kayaks out on the river, we floated in the tubes, we had brought our fishing poles and did some fishing and had a fire. It was so quiet and peaceful. Honestly I would’ve loved to stay longer there was no shortage of things to do. They had everything we needed there. Robert the property manager was so responsive and was very helpful as well. I highly recommend coming to this cute cottage and experiencing it for yourself! We will...
United States
Samantha W.
The price is CA $349
CA $427 total
includes taxes & fees
Oct 12 - Oct 13
Riverfront Retreat | Fire, Sunroom, Kayaks, Tubes
A wooden cabin interior with a large wooden dining table, kitchen area with appliances, and large windows.

4. Riverfront | Hot Tub, Fireplace, Kayaks & Tubes

Riverfront | Hot Tub, Fireplace, Kayaks & Tubes
Evart
10.0 out of 10, Exceptional, (22 reviews)
"Nice winter get away! Host was very responsive, cabin was clean and had all the basic amenities you could need for a long weekend. Overall great cabin! "
United States
Kim D.
The price is CA $410
CA $505 total
includes taxes & fees
Oct 13 - Oct 14
Riverfront | Hot Tub, Fireplace, Kayaks & Tubes
A log cabin with a wooden porch, a grill, and a number '982' on the door.

5. Luxe Log Chalet | Sauna, River, Fire, Kayaks/Tubes

Luxe Log Chalet | Sauna, River, Fire, Kayaks/Tubes
Hersey
9.6 out of 10, Exceptional, (25 reviews)
"We really enjoyed our stay in this comfortable and private retreat. The bonfire area was great and the house had everything we needed. "
United States
Ben B.
The price is CA $430
CA $528 total
includes taxes & fees
Oct 14 - Oct 15
Luxe Log Chalet | Sauna, River, Fire, Kayaks/Tubes
A cabin surrounded by a forest with a small stream and a wooden dock.

6. A-Frame | Hot Tub, Fireplace, River, Kayaks &Tubes

A-Frame | Hot Tub, Fireplace, River, Kayaks &Tubes
Sears
9.4 out of 10, Exceptional, (22 reviews)
"Had a relaxing stay and enjoyed close hiking trails"
United States
Scott F.
The price is CA $394
CA $482 total
includes taxes & fees
Oct 21 - Oct 22
A-Frame | Hot Tub, Fireplace, River, Kayaks &Tubes
A wooden gazebo with benches and a hanging chair, surrounded by trees and a grassy area.

7. Riverside Retreat | Sauna, Fireplace, Kayaks/Tubes

Riverside Retreat | Sauna, Fireplace, Kayaks/Tubes
Hersey
9.4 out of 10, Exceptional, (14 reviews)
"Great place to stay. The property was private and comfortable, and the outdoor grill areas were awesome. We really enjoyed the river access, and the big yard was perfect for playing lawn games all day. Overall, it was a perfect spot for a weekend getaway!"
United States
Justin N.
The price is CA $447
CA $550 total
includes taxes & fees
Oct 18 - Oct 19
Riverside Retreat | Sauna, Fireplace, Kayaks/Tubes
A cabin with a wooden deck and a second-story balcony overlooking a river, surrounded by dense green forest.

8. Secluded Riverfront Cottage | Sauna, Fire & Kayaks

Secluded Riverfront Cottage | Sauna, Fire & Kayaks
Evart
8.6 out of 10, Excellent, (7 reviews)
"Lovely spot to get in touch with nature :)"
United States
Patrick S.
The price is CA $404
CA $499 total
includes taxes & fees
Oct 12 - Oct 13
Secluded Riverfront Cottage | Sauna, Fire & Kayaks
A cabin with a deck and a river in the foreground.

9. Riverfront | Hot Tub, Fireplace, Kayaks & Tubes

Riverfront | Hot Tub, Fireplace, Kayaks & Tubes
Reed City
9.8 out of 10, Exceptional, (18 reviews)
"The host was very responsive, the house was very clean, quiet and cozy. Perfect for a weekend getaway! Will definitely be back!! "
United States
Ariel O.
The price is CA $433
CA $532 total
includes taxes & fees
Oct 15 - Oct 16
Riverfront | Hot Tub, Fireplace, Kayaks & Tubes
A wooden cabin interior with a dining area, kitchen, and a staircase leading to an upper level.

10. Secluded | Sauna, Fire Pit & 20 Acres of Trails

Secluded | Sauna, Fire Pit & 20 Acres of Trails
Evart
9.0 out of 10, Wonderful, (8 reviews)
"Great cabin very clean and comfortable. Excellent communication with the owner. Highly recommend staying for a long weekend. "
United States
J M.
The price is CA $404
CA $496 total
includes taxes & fees
Oct 26 - Oct 27
Secluded | Sauna, Fire Pit & 20 Acres of Trails
A modern kitchen with a granite countertop, stainless steel sink, and wooden shelves. There is a large window with a view of trees and a bench with a blanket.

11. On-site Trails & Trout Stream! NW Michigan Escape

On-site Trails & Trout Stream! NW Michigan Escape
3.0 star property
Hersey
The price is CA $223
CA $375 total
includes taxes & fees
Oct 20 - Oct 21
On-site Trails & Trout Stream! NW Michigan Escape
A wooden cabin interior with a large wooden dining table, kitchen area with appliances, and large windows.

12. Two Riverfront Homes | Hot Tub, Sauna, Kayaks + More

Two Riverfront Homes | Hot Tub, Sauna, Kayaks + More
Evart
The price is CA $970
CA $1,195 total
includes taxes & fees
Oct 13 - Oct 14
Two Riverfront Homes | Hot Tub, Sauna, Kayaks + More
A yurt interior with a wooden bed, a sofa, a woven chair, and a patterned rug.

13. Yurt at Gray’s Riverside Camp

Yurt at Gray’s Riverside Camp
Big Rapids
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely what we were looking for. A nice, relaxing night away before a pheasant hunt on Sunday. The temp was a little chilly at night but the space heater provided enough heat that we were very comfortable in the Yurt. Close to the showers and restroom. Highly recommend."
United States
Janae
The price is CA $71
CA $135 total
includes taxes & fees
Oct 11 - Oct 12
Yurt at Gray’s Riverside Camp
A compact kitchen with a microwave, stove, and refrigerator.

14. Delightful 1-bedroom recreational vehicle with AC in Paris!

Delightful 1-bedroom recreational vehicle with AC in Paris!
Paris
The price is CA $186
CA $261 total
includes taxes & fees
Oct 13 - Oct 14
Delightful 1-bedroom recreational vehicle with AC in Paris!
Property amenity

15. Chippewa Bluffs Resort

Chippewa Bluffs Resort
3.0 star property
Chippewa Lake
9.6 out of 10, Exceptional, (22 reviews)
"The property was beautiful. We had a very awesome view overlooking Chippewa Lake!! We definitely will be back."
United States
Andrew
The price is CA $98
CA $285 total
includes taxes & fees
Oct 13 - Oct 14
Chippewa Bluffs Resort
Two small cabins with a snow-covered ground, a table, and a grill outside.

16. Week/ Weekend Cabin Rental #2

Week/ Weekend Cabin Rental #2
Luther
9.4 out of 10, Exceptional, (26 reviews)
"Home away from home. "
United States
Thomas P.
The price is CA $142
CA $171 total
includes taxes & fees
Oct 12 - Oct 13
Week/ Weekend Cabin Rental #2
A multi-tiered metal stand with kitchenware and a coffee maker.

17. Gray’s Riverside Camp Cabin 4

Gray’s Riverside Camp Cabin 4
Big Rapids
9.6 out of 10, Exceptional, (30 reviews)
"Really fun little cabin to stay at, comfy with an air conditioner too!"
United States
Louis Y.
The price is CA $142
CA $260 total
includes taxes & fees
Oct 12 - Oct 13
Gray’s Riverside Camp Cabin 4
A lakeside view with a gazebo, chairs, and a tree.

18. Cozy 1 Bdrm cabin/sleeps 4. Fireplace/Lakefront/Kayaks and pedal boat included

Cozy 1 Bdrm cabin/sleeps 4. Fireplace/Lakefront/Kayaks and pedal boat included
Remus
10.0 out of 10, Exceptional, (26 reviews)
"The place was lovely, quaint and comfortable. The view and access to the lake was perfect!We will definitely come back!Leslie"
United States
Leslie M.
The price is CA $178
CA $311 total
includes taxes & fees
Oct 25 - Oct 26
Cozy 1 Bdrm cabin/sleeps 4. Fireplace/Lakefront/Kayaks and pedal boat included
A single-story mobile home with a number '3' on the side, a small porch, and a well-maintained lawn.

19. Twin bed cottage on Chippewa Lake with pickleball court

Twin bed cottage on Chippewa Lake with pickleball court
Chippewa Lake
10.0 out of 10, Exceptional, (3 reviews)
"We had a great time at Chippewa Lake! Cabin was clean, had everything we needed, the set up for a camp fire including the wood! We will be back! Great place to stay! A wonderful and relaxing time😊"
United States
Karla D.
The price is CA $123
CA $333 total
includes taxes & fees
Oct 11 - Oct 12
Twin bed cottage on Chippewa Lake with pickleball court
A laundry room with a table, washing machines, and a door labeled 'Employee Only.'

20. Cozy furnished room with AC

Cozy furnished room with AC
Paris
The price is CA $102
CA $131 total
includes taxes & fees
Oct 23 - Oct 24
Cozy furnished room with AC
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

Osceola Grand Hotel

Osceola Grand Hotel

8/10 Good
"My stay was a short in late and out early the next morning. The hotel was clean and rates good for me."
Karen 1-night trip
Posted 1 day ago
Osceola Grand Hotel

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 $178 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. 

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