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

Osceola Vacation Rentals

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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.
$121 nightly
The price is $133
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.
$223 nightly
The price is $247
Sep 22 - Sep 23
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)
"Great location in the heart of Taylor's Falls and the room was well furnished and very clean. Overall a great stay!"
United States
Jacob P.
$182 nightly
The price is $201
Sep 20 - Sep 21
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 20 - Sep 21
Total with taxes and fees
Lovers Lookout 2 at Big Rock Creek
Exterior

5. 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 20 - Sep 21
Total with taxes and fees
Lovers Lookout 3 at Big Rock Creek
Smart TV

6. Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (43 reviews)
"Thanks for a lovely stay!"
United States
Megan J.
$333 nightly
The price is $377
Sep 21 - Sep 22
Total with taxes and fees
Scandinavian Retreat
Terrace/patio

7. 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 21 - Sep 22
Total with taxes and fees
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
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, (26 reviews)
"Good place to stay."
United States
Douglas J.
$182 nightly
The price is $201
Sep 20 - Sep 21
Total with taxes and fees
Cambrian & Co. Loft Cozy, Charming, Downtown Ease
Interior

9. Classic Home

Classic Home
Centuria
8.2 out of 10, Very good, (40 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
$216 nightly
The price is $228
Sep 21 - Sep 22
Total with taxes and fees
Classic Home
Interior

10. Riverside Historic Home near Downtown, Wineries, Hiking

Riverside Historic Home near Downtown, Wineries, Hiking
Taylors Falls
10.0 out of 10, Exceptional, (21 reviews)
"The house was adorable. Clean, organized with personal touches everywhere. The host Andrea was amazing. Would recommend."
United States
Abigail T.
Riverside Historic Home near Downtown, Wineries, Hiking
Interior

11. 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 20 - Sep 21
Total with taxes and fees
Cozy 3-bedroom cabin on Cedar Lake
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.
$283 nightly
The price is $312
Sep 20 - Sep 21
Total with taxes and fees
Nordic Harbor | Room 5 | Cedar Shadows
Terrace/patio

13. Private Suite in historic Stillwater North Hill

Private Suite in historic Stillwater North Hill
Stillwater
10.0 out of 10, Exceptional, (47 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
$221 nightly
The price is $241
Sep 20 - Sep 21
Total with taxes and fees
Private Suite in historic Stillwater North Hill
3 bedrooms, desk, travel crib, WiFi

14. Private riverfront cabin with wooded hiking trails

Private riverfront cabin with wooded hiking trails
Amery
9.4 out of 10, Exceptional, (3 reviews)
"What a beautiful getaway… Charming, amazing property , very relaxing, just lovely!"
United States
Chris D.
$327 nightly
The price is $345
Sep 22 - Sep 23
Total with taxes and fees
Private riverfront cabin with wooded hiking trails
Outdoor dining

15. Lovers Lookout 1: Where Rustic Meets Luxury at Big Rock Creek

Lovers Lookout 1: Where Rustic Meets Luxury at Big Rock Creek
Saint Croix Falls
10.0 out of 10, Exceptional, (1 review)
"Everything was clean and nice when we arrived. Check in was easy by text. We were greatedby the owners not long after check in and they delivered us firewood that we purchased. Was an amazing stay and we hope to come back every year !"
United States
Jenny E.
$167 nightly
The price is $173
Sep 21 - Sep 22
Total with taxes and fees
Lovers Lookout 1: Where Rustic Meets Luxury at Big Rock Creek
Interior

16. Apple River Retreat home in Amery

Apple River Retreat home in Amery
Amery
10.0 out of 10, Exceptional, (7 reviews)
"Great last minute find for weekend!"
United States
Dan W.
$216 nightly
The price is $228
Sep 21 - Sep 22
Total with taxes and fees
Apple River Retreat home in Amery
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, (9 reviews)
$421 nightly
The price is $465
Sep 21 - Sep 22
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.
$204 nightly
The price is $226
Sep 29 - Sep 30
Total with taxes and fees
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC
Property grounds

19. 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
$195 nightly
The price is $196
Sep 21 - Sep 22
Total with taxes and fees
Gorgeous A-Frame with Panoramic Views, Nestled Atop White Oak Ridge, Wisconsin
Desk, iron/ironing board, WiFi (free), bed sheets

20. Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very good, (919 reviews)
"Friendly staff and safe place to stay."
United States
Terry
$86 nightly
The price is $93
Oct 18 - Oct 19
Total with taxes and fees
Hudson Inn & Suites
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

Best Western Plus Hudson I-94

Best Western Plus Hudson I-94

8/10 Good
"Overall the hotel was inviting with great staff but many things were missing in rooms or things were not kept up well. We switched rooms three times due to a fridge that wasn't working, a terrible smell in a room from repairs and our third refrigerator leaked on the floor. The key cards did not work consistently which was frustrating to have to use multiple times or go back down to the front desk to have them reset."
Janice 2-night trip
Posted 18 hours ago
Best Western Plus Hudson I-94

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 $93 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 1880s Home: This highly rated vacation home rental in Osceola is located on a river and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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.