A waterfall cascading over a rocky cliff surrounded by lush greenery.

Osceola Holiday Rentals

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Our top choices for Osceola holiday rentals

1. Cozy Mother-in-Law Apartment

Cozy Mother-in-Law Apartment
Osceola
10.0 out of 10, Exceptional, (52 reviews)
"Would absolutely stay here again! Lovely location, clean, communicative host, and they shoveled right when it snowed which was especially helpful when I had a 5am clinical rotation!"
United States
Mallorey K.
The price is AU$218
includes taxes & fees
17 Aug - 18 Aug
Cozy Mother-in-Law Apartment

2. Historic 1880s Home

Historic 1880s Home
Osceola
10.0 out of 10, Exceptional, (80 reviews)
"Great spot to stay for the weekend. Close proximity to downtown. "
United States
Connie S.
The price is AU$378
includes taxes & fees
14 Sept - 15 Sept
Historic 1880s Home

3. White Bear Lake House 3 blocks from Downtown and Lake!

White Bear Lake House 3 blocks from Downtown and Lake!
White Bear Lake
The price is AU$363
includes taxes & fees
16 Aug - 17 Aug
White Bear Lake House 3 blocks from Downtown and Lake!

4. Cozy 3-bedroom cabin on Cedar Lake

Cozy 3-bedroom cabin on Cedar Lake
Star Prairie
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved our stay. What started as a simple family weekend at the lake turned into one of those trips we’ll remember for a long time.Our boys practically lived on the dock. They fished for hours, celebrated every catch like it was a trophy fish, and couldn’t wait to get back out there the next morning. We cooked what they caught, spent our evenings by the water, and genuinely enjoyed just being together without needing an itinerary or much of anything else.There’s something special...
United States
Mike R.
The price is AU$619
includes taxes & fees
21 Aug - 22 Aug
Cozy 3-bedroom cabin on Cedar Lake

5. Wannigan Point Cabin #4

Wannigan Point Cabin #4
Taylors Falls
10.0 out of 10, Exceptional, (2 reviews)
"Everything was as expected- very clean and well maintained. "
United States
Breanne B.
The price is AU$328
includes taxes & fees
16 Aug - 17 Aug
Wannigan Point Cabin #4

6. Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm

Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
Taylors Falls
9.8 out of 10, Exceptional, (12 reviews)
"Convenient downtown location allowing us to just walk to restaurants/bars, coffee, and the state park for hiking. "
United States
Rhonda R.
The price is AU$277
includes taxes & fees
16 Aug - 17 Aug
Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm

7. Lovers Lookout 2 at Big Rock Creek

Lovers Lookout 2 at Big Rock Creek
Saint Croix Falls
10.0 out of 10, Exceptional, (1 review)
"We enjoyed everything about our stay! Just wish we had more time to enjoy the amenities of the property. "
United States
Kim J.
The price is AU$221
includes taxes & fees
14 Sept - 15 Sept
Lovers Lookout 2 at Big Rock Creek

8. Lovers Lookout 3 at Big Rock Creek

Lovers Lookout 3 at Big Rock Creek
Saint Croix Falls
9.8 out of 10, Exceptional, (6 reviews)
"We had an amazing time. The set up is so cute and it’s very peaceful. Very comfortable beds and extremely clean. Loved it!"
United States
Jessica O.
The price is AU$225
includes taxes & fees
15 Sept - 16 Sept
Lovers Lookout 3 at Big Rock Creek

9. The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge

The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
Saint Croix Falls
10.0 out of 10, Exceptional, (1 review)
"Great experience"
United States
Lori M.
The price is AU$251
includes taxes & fees
24 Aug - 25 Aug
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge

10. Wannigan Point Cabin #2

Wannigan Point Cabin #2
Taylors Falls
10.0 out of 10, Exceptional, (5 reviews)
"I had a great stay at Wannigan Point. The cabin was exactly what I needed, very quiet despite being quite close to town. Plenty of shops, restaurants, and nature nearby."
United States
Elijah T.
The price is AU$328
includes taxes & fees
16 Aug - 17 Aug
Wannigan Point Cabin #2

11. Cambrian & Co. Loft Cozy, Charming, Downtown Ease

Cambrian & Co. Loft Cozy, Charming, Downtown Ease
Taylors Falls
10.0 out of 10, Exceptional, (21 reviews)
"Good place to stay."
United States
Douglas J.
The price is AU$276
includes taxes & fees
24 Aug - 25 Aug
Cambrian & Co. Loft Cozy, Charming, Downtown Ease

12. Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (43 reviews)
"Thanks for a lovely stay!"
United States
Megan J.
The price is AU$571
includes taxes & fees
19 Aug - 20 Aug
Scandinavian Retreat

13. Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very good, (892 reviews)
"Older hotel but well maintained and great value for the price."
United States
Dennis
The price is AU$136
includes taxes & fees
17 Aug - 18 Aug
Hudson Inn & Suites

14. Wannigan Point Cabin #3

Wannigan Point Cabin #3
Taylors Falls
8.0 out of 10, Very good, (2 reviews)
"Very nice and clean cabin with plenty of room to move around. Since it was cool outside, the wood stove made for a cozy atmosphere."
United States
Lisa M.
The price is AU$328
includes taxes & fees
16 Aug - 17 Aug
Wannigan Point Cabin #3

15. Wannigan Point Cabin #5

Wannigan Point Cabin #5
Taylors Falls
7.4 out of 10, Good, (3 reviews)
"Very cute and comfy cabin! It was the perfect location for us as we were in town for Hay Days. "
United States
Deanna N.
The price is AU$328
includes taxes & fees
16 Aug - 17 Aug
Wannigan Point Cabin #5

16. Classic Home

Classic Home
Centuria
8.0 out of 10, Very good, (39 reviews)
"Nice clean house that fit our needs perfectly. Were on girls weekend and this was great place to stay and then travel around the wider area trying different routes and restaurants. Got great suggestions from the host! "
United States
Melissa
The price is AU$324
includes taxes & fees
19 Aug - 20 Aug
Classic Home

17. Wannigan Point Cabin #1

Wannigan Point Cabin #1
Taylors Falls
7.0 out of 10, Good, (2 reviews)
"Nice midsized cabin with all the amenities. Quiet for the most part (trucks on the highway nearby). Communication with Mariah was very clear. We enjoyed our little “retreat”."
United States
Eric O.
The price is AU$328
includes taxes & fees
16 Aug - 17 Aug
Wannigan Point Cabin #1

18. Gorgeous A-Frame with Panoramic Views, Nestled Atop White Oak Ridge, Wisconsin

Gorgeous A-Frame with Panoramic Views, Nestled Atop White Oak Ridge, Wisconsin
Saint Croix Falls
The price is AU$264
includes taxes & fees
1 Sept - 2 Sept
Gorgeous A-Frame with Panoramic Views, Nestled Atop White Oak Ridge, Wisconsin

19. Large tent on massive Big Rock Creek Estate!

Large tent on massive Big Rock Creek Estate!
Saint Croix Falls
The price is AU$361
includes taxes & fees
17 Aug - 18 Aug
Large tent on massive Big Rock Creek Estate!

20. Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC

Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC
Somerset
10.0 out of 10, Exceptional, (14 reviews)
"Very clean and exactly as described, would stay again! "
United States
Thomas R.
The price is AU$334
includes taxes & fees
17 Aug - 18 Aug
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, 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 Hotel Reviews

Find out more about Osceola

Everything you need to know about Osceola 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 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Osceola holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osceola. 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 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 holiday rentals we have selected for you start as low as AU$136 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Osceola rentals

At Expedia, we put the best Osceola 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 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 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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Osceola?

Yes, there are holiday rentals in Osceola close to Osceola & St. Croix Valley Railway, or you can select a more secluded option if you're looking for a relaxing stay. Osceola is known for its riverfront and bars. Make sure you have time to check out the waterfalls and entertainment choices during your trip.

What are some of the best holiday rentals that Osceola has to offer?

MINNeSTAY* St. Croix Valley Inn: This highly rated holiday home rental in Osceola is located on the waterfront, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Osceola?

Choose from 7 Expedia holiday rentals in Osceola for a memorable holiday.

What can I see and do in Osceola?

Saint Croix River and Apple River are a couple of lovely local spots to get outside and enjoy nature. Osceola & St. Croix Valley Railway and Trollhaugen are other places to visit while you're in town.

What are holiday rentals like in Osceola?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osceola. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.