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

Osceola Vacation Rentals

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

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.
$137 nightly
The price is $151
Sep 22 - Sep 23
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, (80 reviews)
"Great spot to stay for the weekend. Close proximity to downtown. "
United States
Connie S.
$223 nightly
The price is $247
Sep 1 - Sep 2
Total with taxes and fees
Historic 1880s Home
Desk, iron/ironing board, WiFi (free), bed sheets

3. Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very Good, (899 reviews)
"Older hotel but well maintained and great value for the price."
United States
Dennis
$86 nightly
The price is $94
Sep 8 - Sep 9
Total with taxes and fees
Hudson Inn & Suites
Exterior detail

4. 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)
$423 nightly
The price is $454
Aug 23 - Aug 24
Total with taxes and fees
Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.
Property grounds

5. Nordic Harbor | Room 5 | Cedar Shadows

Nordic Harbor | Room 5 | Cedar Shadows
Center City
9.8 out of 10, Exceptional, (10 reviews)
"VRBO makes a quick getaway so seamless. Stayed in town for a family wedding and could not have been happier with the location. Great rooftop bar with craft cocktails and good beer wine selection. Soon to have restaurant. Gift/essential shop below bar. Really nice people and great view."
United States
Karie S.
$283 nightly
The price is $311
Aug 24 - Aug 25
Total with taxes and fees
Nordic Harbor | Room 5 | Cedar Shadows
Property grounds

6. Historic Swedish Cottage on Quiet Lindstrom Lake

Historic Swedish Cottage on Quiet Lindstrom Lake
Lindstrom
9.4 out of 10, Exceptional, (246 reviews)
"Beautiful home. Well equipped kitchen. Lots of room for everyone "
United States
Sue P.
$686 nightly
The price is $737
Aug 23 - Aug 24
Total with taxes and fees
Historic Swedish Cottage on Quiet Lindstrom Lake
Outdoor dining

7. 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.
$413 nightly
The price is $453
Aug 24 - Aug 25
Total with taxes and fees
Nordic Harbor | Room 3 | Arctic Pine - Suite
Coffee/tea maker, fridge, microwave, oven

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

Cambrian & Co. Loft Cozy, Charming, Downtown Ease
Taylors Falls
10.0 out of 10, Exceptional, (24 reviews)
"Good place to stay."
United States
Douglas J.
$183 nightly
The price is $197
Aug 24 - Aug 25
Total with taxes and fees
Cambrian & Co. Loft Cozy, Charming, Downtown Ease
Smart TV

9. Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (43 reviews)
"Thanks for a lovely stay!"
United States
Megan J.
$344 nightly
The price is $378
Sep 8 - Sep 9
Total with taxes and fees
Scandinavian Retreat
Interior

10. 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.
$594 nightly
The price is $653
Sep 17 - Sep 18
Total with taxes and fees
Riverside Historic Home near Downtown, Wineries, Hiking
Outdoor dining

11. Escape to The Clubhouse, St. Croix Falls city, Wisconsin

Escape to The Clubhouse, St. Croix Falls city, Wisconsin
Saint Croix Falls
$771 nightly
The price is $814
Aug 23 - Aug 24
Total with taxes and fees
Escape to The Clubhouse, St. Croix Falls city, Wisconsin
Private kitchen

12. 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.
$215 nightly
The price is $232
Aug 23 - Aug 24
Total with taxes and fees
Wannigan Point Cabin #2
Property grounds

13. Nordic Harbor | Room 6 | Silver Birch - Suite

Nordic Harbor | Room 6 | Silver Birch - Suite
Center City
10.0 out of 10, Exceptional, (2 reviews)
"Do not hesitate to book at Nordic Harbor. The rooms are stellar and the location is convenient. Steps away from the room is the Nordic Harbor market and roof top bar. The onsite pontoon rental is a blast, and the lake is beautiful. If you're looking for a quick getaway from the cities, this is it!"
United States
Paul F.
$413 nightly
The price is $453
Aug 27 - Aug 28
Total with taxes and fees
Nordic Harbor | Room 6 | Silver Birch - Suite
Terrace/patio

14. 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
Aug 24 - Aug 25
Total with taxes and fees
Gorgeous A-Frame with Panoramic Views, Nestled Atop White Oak Ridge, Wisconsin
1 bedroom, WiFi, bed sheets

15. 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
Aug 27 - Aug 28
Total with taxes and fees
Nordic Harbor | Room 1 | Acorn Oak
Outdoor dining

16. 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
Aug 24 - Aug 25
Total with taxes and fees
Lovers Lookout 2 at Big Rock Creek
Terrace/patio

17. 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
Aug 24 - Aug 25
Total with taxes and fees
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
Smart TV, fireplace

18. 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.
$183 nightly
The price is $197
Aug 24 - Aug 25
Total with taxes and fees
Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
Exterior

19. Creekside Group Glamp Site at Big Rock Creek!

Creekside Group Glamp Site at Big Rock Creek!
Saint Croix Falls
$337 nightly
The price is $350
Aug 24 - Aug 25
Total with taxes and fees
Creekside Group Glamp Site at Big Rock Creek!
Coffee/tea maker, fridge, microwave, cookware/dishes/utensils

20. Nordic Harbor | Room 4 | Nordic Spruce

Nordic Harbor | Room 4 | Nordic Spruce
Center City
$283 nightly
The price is $311
Aug 23 - Aug 24
Total with taxes and fees
Nordic Harbor | Room 4 | Nordic Spruce
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

Water Street Inn

Water Street Inn

10/10 Excellent
"Loved our stay!"
Sara 2-night trip
Posted 2 hours ago
Water Street Inn

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 $94 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?

Sleepy Deer Chalet! Spacious, Well-Appointed home on Beautiful Lake Wapogasset!: This vacation home rental outside of Osceola is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden 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.