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

Osceola Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Osceola vacation rentals

Exterior

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.
$141 nightly
The price is $156
Sep 29 - Sep 30
Total with taxes and fees
Cozy Mother-in-Law Apartment
Interior

2. Historic 1880s Home

Historic 1880s Home
Osceola
10.0 out of 10, Exceptional, (83 reviews)
"Rooms are clean, kitchen is well supplied. If you enjoy staying at historic buildings, this would be a good fit for you."
United States
Kathleen R.
$232 nightly
The price is $257
Sep 9 - Sep 10
Total with taxes and fees
Historic 1880s Home
Smart TV, fireplace

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

Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
Taylors Falls
9.8 out of 10, Exceptional, (13 reviews)
"Convenient downtown location allowing us to just walk to restaurants/bars, coffee, and the state park for hiking. "
United States
Rhonda R.
$183 nightly
The price is $197
Sep 3 - Sep 4
Total with taxes and fees
Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
3 bedrooms, iron/ironing board, travel crib, WiFi (free)

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.
$426 nightly
The price is $449
Sep 3 - Sep 4
Total with taxes and fees
Cozy 3-bedroom cabin on Cedar Lake
Smart TV

5. Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (43 reviews)
"Thanks for a lovely stay!"
United States
Megan J.
$368 nightly
The price is $405
Sep 14 - Sep 15
Total with taxes and fees
Scandinavian Retreat
Outdoor dining

6. 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.
$149 nightly
The price is $154
Sep 13 - Sep 14
Total with taxes and fees
Lovers Lookout 2 at Big Rock Creek
Coffee/tea maker, fridge, microwave, oven

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

Cambrian & Co. Loft Cozy, Charming, Downtown Ease
Taylors Falls
10.0 out of 10, Exceptional, (26 reviews)
"Good place to stay."
United States
Douglas J.
$183 nightly
The price is $197
Sep 3 - Sep 4
Total with taxes and fees
Cambrian & Co. Loft Cozy, Charming, Downtown Ease
Private kitchen

8. 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.
$286 nightly
The price is $309
Sep 6 - Sep 7
Total with taxes and fees
Wannigan Point Cabin #3
Terrace/patio

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.
$171 nightly
The price is $178
Sep 7 - Sep 8
Total with taxes and fees
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
Exterior

10. 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.
$149 nightly
The price is $154
Sep 21 - Sep 22
Total with taxes and fees
Lovers Lookout 3 at Big Rock Creek
1 bedroom, WiFi, bed sheets

11. Nordic Harbor | Room 1 | Acorn Oak

Nordic Harbor | Room 1 | Acorn Oak
Center City
10.0 out of 10, Exceptional, (2 reviews)
"Our stay was wonderful---quaint, modern-rustic and very comfortable. We loved being able to walk across the parking lot to the rooftop bar."
United States
Alisha H.
$283 nightly
The price is $311
Sep 3 - Sep 4
Total with taxes and fees
Nordic Harbor | Room 1 | Acorn Oak
Desk, iron/ironing board, WiFi (free), bed sheets

12. Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very Good, (907 reviews)
"Friendly staff and safe place to stay."
United States
Terry
$96 nightly
The price is $104
Sep 3 - Sep 4
Total with taxes and fees
Hudson Inn & Suites
Interior

13. 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
$210 nightly
The price is $222
Sep 3 - Sep 4
Total with taxes and fees
Classic Home
Exterior detail

14. Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.

Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.
center city
10.0 out of 10, Exceptional, (7 reviews)
$422 nightly
The price is $453
Sep 6 - Sep 7
Total with taxes and fees
Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.
Terrace/patio

15. 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
$188 nightly
The price is $189
Sep 7 - Sep 8
Total with taxes and fees
Gorgeous A-Frame with Panoramic Views, Nestled Atop White Oak Ridge, Wisconsin
Interior

16. Riverside Historic Home near Downtown, Wineries, Hiking

Riverside Historic Home near Downtown, Wineries, Hiking
Taylors Falls
10.0 out of 10, Exceptional, (19 reviews)
"The house was adorable. Clean, organized with personal touches everywhere. The host Andrea was amazing. Would recommend."
United States
Abigail T.
$577 nightly
The price is $635
Sep 17 - Sep 18
Total with taxes and fees
Riverside Historic Home near Downtown, Wineries, Hiking
Private kitchen

17. Scenic Apple River Retreat - Spacious 4BR Home - Fishing, Tubing & Kayaking

Scenic Apple River Retreat - Spacious 4BR Home - Fishing, Tubing & Kayaking
Somerset
10.0 out of 10, Exceptional, (1 review)
"Mike was a great host and was FAST at communicating. I need to comment that I only gave 4 stars on cleaning. On special request, the host got the house ready a week early on the condition I agreed that it was not quite ready to his normal standards and we were the first guests ever in his new property. The yard was huge, no next neighbors crowding you. Kitchen has everything. Bathrooms furnished with towels, soaps, shampoo, etc. The river is just behind the house. We had fun wading,...
United States
David
$426 nightly
The price is $449
Sep 8 - Sep 9
Total with taxes and fees
Scenic Apple River Retreat - Spacious 4BR Home - Fishing, Tubing & Kayaking
Terrace/patio

18. Huge tent with AC at Big Rock Creek

Huge tent with AC at Big Rock Creek
Saint Croix Falls
$203 nightly
The price is $210
Sep 14 - Sep 15
Total with taxes and fees
Huge tent with AC at Big Rock Creek
Outdoor dining

19. Nordic Harbor | Room 3 | Arctic Pine - Suite

Nordic Harbor | Room 3 | Arctic Pine - Suite
Center City
10.0 out of 10, Exceptional, (1 review)
"Beautiful place and will be staying there again. "
United States
SUZANNE M.
$412 nightly
The price is $452
Sep 7 - Sep 8
Total with taxes and fees
Nordic Harbor | Room 3 | Arctic Pine - Suite
Interior

20. 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.
$281 nightly
The price is $304
Sep 6 - Sep 7
Total with taxes and fees
Wannigan Point Cabin #1
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osceola Hotel Reviews

Holiday Inn Express & Suites Hudson I-94 by IHG

Holiday Inn Express & Suites Hudson I-94 by IHG

10/10 Excellent
"Clean and friendly! Breakfast was also really good."
David 1-night trip
Posted 5 hours ago
Holiday Inn Express & Suites Hudson I-94 by IHG

Find out more about Osceola

Everything you need to know about Osceola 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 vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osceola vacation 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 low season months. For more hustle and bustle, you may prefer to visit Osceola in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $104 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osceola rentals

At Expedia, we put the best Osceola 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 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 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. 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

Frequently asked questions

Can I find a vacation rental in Osceola?

Yes, you can find vacation rentals in Osceola near Osceola & St. Croix Valley Railway, or you can go with a secluded option if you're looking for extra privacy while you relax. 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 vacation home rentals that Osceola has to offer?

Historic Swedish Cottage on Quiet Lindstrom Lake: This vacation home rental outside of Osceola is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a private yard and a selection of games.

How many vacation rentals are there in Osceola?

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

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 vacation rentals like in Osceola?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Osceola. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.