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Vacation Rentals in Osceola County

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Top Cities in Osceola County

Top Vacation Rentals in Osceola County

Family/Friend Retreat on Hersey River, close to trails, golf & horseback riding

2.0 star property
10.0 out of 10, Exceptional, (3)
"This was the perfect spot for our visit with great access to the White Pine Trail. The rental was clean and comfy and had everything we needed for a great visit. "
Family/Friend Retreat on Hersey River, close to trails, golf & horseback riding

Maple Lane Lake House

10.0 out of 10, Exceptional, (58)
"Host was great, cabin was well outfitted. Will highly recommend."
Maple Lane Lake House

The Little A frame

9.6 out of 10, Exceptional, (38)
"Was a good in clean cabin "
The Little A frame

Adult Themed Cabin w/ Hot Tub

10.0 out of 10, Exceptional, (32)
"Great place for a romantic getaway "
Adult Themed Cabin w/ Hot Tub

Big Red Lakefront Getaway & Golf Retreat at Canadian Lakes

10.0 out of 10, Exceptional, (45)
"Great family time celebrating anniversaries and Father’s Day! Loved the boat, Fire pit and kayaks. "
Big Red Lakefront Getaway & Golf Retreat at Canadian Lakes

Charming cabin with indoor Pickleball court! Unlimited access during the weekday

9.8 out of 10, Exceptional, (20)
"Great property and freindly staff and other campers on site "
$130 nightly
The price is $137
Oct 5 - Oct 6
Total with taxes and fees
Charming cabin with indoor Pickleball court! Unlimited access during the weekday

Woodward Lake Sanctuary - Perfect Getaway Minutes From Town

9.8 out of 10, Exceptional, (80)
"We loved our stay, the property was gorgeous, everything was very clean, we loved the chocolates on the bed and the extra little tidbits that made it feel homey!"
Woodward Lake Sanctuary - Perfect Getaway Minutes From Town

Dog friendly cozy red cottage near lakes and trails

9.6 out of 10, Exceptional, (32)
"We enjoyed our stay at this cabin. It is very comfortable for small groups and clean. The location is great and walking distance to lakes. We’ll book it again when we come back!"
Dog friendly cozy red cottage near lakes and trails

Secluded Cabin on the Muskegon River, 40 Acres of Private Land, ORV Trail Access

10.0 out of 10, Exceptional, (57)
"Was a fantastic place to stay. This place is a hidden gem!! Would highly recommend!!"
Secluded Cabin on the Muskegon River, 40 Acres of Private Land, ORV Trail Access

Charming Renovated Cabin with a Cottage vibe. Thus "The Cabbage"

9.6 out of 10, Exceptional, (113)
"This adorable cabin is in a lovely location. We enjoyed kayaking on the lake, playing music by the picnic table, and enjoying the tranquility. Everything we needed was included!"
Charming Renovated Cabin with a Cottage vibe. Thus "The Cabbage"

Bigfoot themed cottage. Dog friendly!

10.0 out of 10, Exceptional, (19)
"Love the location of the house very easy to find clean very well love the decorations "
$160 nightly
The price is $167
Oct 7 - Oct 8
Total with taxes and fees
Bigfoot themed cottage. Dog friendly!

Birchwood Resort & Campground

3.0 star property
9.2 out of 10, Wonderful, (152)
"The owner is very friendly and the cabin was clean and well kept."
Birchwood Resort & Campground

Chippewa Bluffs Resort

3.0 star property
9.8 out of 10, Exceptional, (8)
"Cute place. Wish we had longer to enjoy it. "
$185 nightly
The price is $189
Oct 5 - Oct 6
Total with taxes and fees
Chippewa Bluffs Resort

Newly Renovated, Lakefront, Dog Friendly Cottage, Sand Lake, Harrison

10.0 out of 10, Exceptional, (9)
Newly Renovated, Lakefront, Dog Friendly Cottage, Sand Lake, Harrison

Lake cabin, indoor Pickleball court, access to ATV trails near Baldwin,MI ,

10.0 out of 10, Exceptional, (11)
"The cabin was tidy and clean and perfectly located near the NCT hiking paths. We also took advantage of the great pickleball court available. Don and Sandra were great hosts. Highly recommended. "
$120 nightly
The price is $126
Oct 5 - Oct 6
Total with taxes and fees
Lake cabin, indoor Pickleball court, access to ATV trails near Baldwin,MI ,

Peaceful Retreat for Families/Couples/Groups - All Sports Lake w/ Kayaks & SUP's

10.0 out of 10, Exceptional, (154)
"The house was perfect for our 3 generations of family. The lake area was quiet with lots of natural wildlife around: herons, loons, songbirds, toads, fish. The grandkids loved it all!"
Peaceful Retreat for Families/Couples/Groups - All Sports Lake w/ Kayaks & SUP's

Cozy Little Cabin #4

2.0 star property
10.0 out of 10, Exceptional, (16)
"Very nice little place, just what I needed "
$160 nightly
The price is $160
Oct 5 - Oct 6
Total with taxes and fees
Cozy Little Cabin #4

LAKE CABIN! Stocked, Wifi Beach Kayaks, Firepit, Trails, Creek Washer Dryer, Pet

2.0 star property
10.0 out of 10, Exceptional, (16)
"For us, it was great. Very enjoyable. "
$154 nightly
The price is $159
Oct 12 - Oct 13
Total with taxes and fees
LAKE CABIN! Stocked, Wifi Beach Kayaks, Firepit, Trails, Creek Washer Dryer, Pet

Fabulous Beach House on All Sports Lake Sapphire! Sleeps 12 and Parking for 12!

10.0 out of 10, Exceptional, (37)
"Great stay, as always!! Kids had great fun at the beach, dock and paddle boards. "
Fabulous Beach House on All Sports Lake Sapphire! Sleeps 12 and Parking for 12!

Great Cozy Cabin, in Lake Community, Private Beach,State land,Trails,Fishing,Orv

8.8 out of 10, Excellent, (16)
"It was peaceful cuz we love it thank you "
$160 nightly
The price is $165
Oct 13 - Oct 14
Total with taxes and fees
Great Cozy Cabin, in Lake Community, Private Beach,State land,Trails,Fishing,Orv
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

Find out more about Osceola County

Discover your perfect Osceola County vacation rental with Expedia

How many vacation rentals are available in Osceola County?


Expedia has plenty of vacation rentals to choose from in and around  Osceola County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Osceola County?


The selection of Osceola County vacation rentals we have selected for you start as low as $126 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Osceola County?


Vacation rentals in Osceola County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Osceola County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Osceola County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. 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. 


How do I find the best deal on a vacation rental in Osceola County?


Find vacation rentals in Osceola County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Osceola County.  


What amenities are available in a vacation rental in Osceola County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Osceola County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Osceola County?   


Everytime is a great time to head to Osceola County! Staying in a Osceola County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Osceola County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Osceola County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Osceola County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Osceola County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.