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Osceola County Holiday Rentals

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Top Holiday Rentals Destinations 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 "
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)
"Beautiful property, great location, very comfortable and a great deal. This is our 3rd year staying here."
Woodward Lake Sanctuary - Perfect Getaway Minutes From Town

Dog friendly cozy red cottage near lakes and trails

9.6 out of 10, Exceptional, (31)
"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 "
The price is NZ$288
includes taxes & fees
5 Oct - 6 Oct
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. "
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. "
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 "
The price is NZ$276
includes taxes & fees
2 Oct - 3 Oct
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. "
The price is NZ$276
includes taxes & fees
2 Oct - 3 Oct
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 home plenty of space, thoughtful provisions, great for families. Beach area is great."
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 "
The price is NZ$285
includes taxes & fees
2 Oct - 3 Oct
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

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$276 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. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia