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 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, (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.
$224 nightly
The price is $248
Sep 15 - Sep 16
Total with taxes and fees
Historic 1880s Home
Living area

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 7 - Sep 8
Total with taxes and fees
Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
Outdoor dining

4. 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 9 - Sep 10
Total with taxes and fees
Lovers Lookout 2 at Big Rock Creek
Terrace/patio

5. 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.
$170 nightly
The price is $177
Sep 7 - Sep 8
Total with taxes and fees
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
Exterior

6. 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 14 - Sep 15
Total with taxes and fees
Lovers Lookout 3 at Big Rock Creek
Living area

7. Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (43 reviews)
"Thanks for a lovely stay!"
United States
Megan J.
$366 nightly
The price is $403
Sep 8 - Sep 9
Total with taxes and fees
Scandinavian Retreat
Private kitchen

8. 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.
$180 nightly
The price is $193
Sep 7 - Sep 8
Total with taxes and fees
Cambrian & Co. Loft Cozy, Charming, Downtown Ease
Interior

9. 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 7 - Sep 8
Total with taxes and fees
Cozy 3-bedroom cabin on Cedar Lake
Room

10. Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very Good, (909 reviews)
"Friendly staff and safe place to stay."
United States
Terry
$81 nightly
The price is $88
Oct 6 - Oct 7
Total with taxes and fees
Hudson Inn & Suites
Interior

11. 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
$215 nightly
The price is $227
Sep 7 - Sep 8
Total with taxes and fees
Classic Home
Property grounds

12. 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.
$282 nightly
The price is $310
Sep 7 - Sep 8
Total with taxes and fees
Nordic Harbor | Room 5 | Cedar Shadows
Property grounds

13. 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

14. 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.
$563 nightly
The price is $619
Sep 17 - Sep 18
Total with taxes and fees
Riverside Historic Home near Downtown, Wineries, Hiking
Terrace/patio

15. Huge tent with AC at Big Rock Creek

Huge tent with AC at Big Rock Creek
Saint Croix Falls
$197 nightly
The price is $204
Sep 14 - Sep 15
Total with taxes and fees
Huge tent with AC at Big Rock Creek
Living area

16. 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
$421 nightly
The price is $444
Sep 8 - Sep 9
Total with taxes and fees
Scenic Apple River Retreat - Spacious 4BR Home - Fishing, Tubing & Kayaking
Exterior detail

17. 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)
$420 nightly
The price is $451
Sep 7 - Sep 8
Total with taxes and fees
Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.
Exterior detail

18. 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, (15 reviews)
"Very clean and exactly as described, would stay again! "
United States
Thomas R.
$215 nightly
The price is $237
Sep 14 - Sep 15
Total with taxes and fees
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC
Exterior

19. Geo Dome at Big Rock Creek!

Geo Dome at Big Rock Creek!
Saint Croix Falls
$268 nightly
The price is $279
Sep 7 - Sep 8
Total with taxes and fees
Geo Dome at Big Rock Creek!
Terrace/patio

20. Private Suite in historic Stillwater North Hill

Private Suite in historic Stillwater North Hill
Stillwater
10.0 out of 10, Exceptional, (44 reviews)
"This suite was perfect! It was little and cute yet had what was needed. The hosts were very responsive and wonderful. Beautiful well kept property. Would definitely recommend!"
United States
Randy
$229 nightly
The price is $249
Sep 8 - Sep 9
Total with taxes and fees
Private Suite in historic Stillwater North Hill
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

Comfort Inn & Suites St. Paul Northeast

Comfort Inn & Suites St. Paul Northeast

10/10 Excellent
"Short vacation with 2 adults and 2 kids (4 and 7). The pool area and waterslide were a hot. Breakfast was solid and the suite was perfect for us to spread out a bit after travelling. Nice, quiet, well-managed hotel. We would go back which is something we don't say too often."
Matthew 1-night trip
Posted 5 hours ago
Comfort Inn & Suites St. Paul Northeast

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 $88 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.