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

Osceola Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Osceola vacation rentals

A two-story house with a front porch, a garage, and a well-maintained lawn.

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.
$116 nightly
The price is $129
Oct 20 - Oct 21
Total with taxes and fees
Cozy Mother-in-Law Apartment
A kitchen with wooden cabinets, a window, a sink, and various kitchen utensils.

2. Historic 1880s Home

Historic 1880s Home
Osceola
9.8 out of 10, Exceptional, (86 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.
$204 nightly
The price is $226
Oct 18 - Oct 19
Total with taxes and fees
Historic 1880s Home
A kitchen with a wooden island, bar stools, a fireplace, and a television.

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.
$180 nightly
The price is $199
Oct 18 - Oct 19
Total with taxes and fees
Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
A modern living room with a spiral staircase, a sofa set, a coffee table, and a chandelier.

4. Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (46 reviews)
"Thanks for a lovely stay!"
United States
Megan J.
$343 nightly
The price is $388
Oct 19 - Oct 20
Total with taxes and fees
Scandinavian Retreat
A hotel room with two beds, green walls, and framed pictures of landscapes.

5. Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.4 out of 10, Very good, (954 reviews)
"Friendly staff and safe place to stay."
United States
Terry
$81 nightly
The price is $88
Oct 19 - Oct 20
Total with taxes and fees
Hudson Inn & Suites
A wooden cabin with a triangular roof, a central door, and a small window.

6. 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.
$191 nightly
The price is $199
Oct 19 - Oct 20
Total with taxes and fees
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
A modern kitchen with black cabinets, a white countertop, and a wooden floor.

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

Cambrian & Co. Loft Cozy, Charming, Downtown Ease
Taylors Falls
10.0 out of 10, Exceptional, (29 reviews)
"Good place to stay."
United States
Douglas J.
$181 nightly
The price is $200
Nov 10 - Nov 11
Total with taxes and fees
Cambrian & Co. Loft Cozy, Charming, Downtown Ease
A bedroom with a wooden ceiling, a bed with a white comforter and patterned pillows, a bedside table with a lamp, and a small table with a potted plant.

8. 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.
$280 nightly
The price is $309
Oct 18 - Oct 19
Total with taxes and fees
Nordic Harbor | Room 1 | Acorn Oak
A cozy cabin interior with a wooden exterior, a green door, a window with a grid pattern, and a rustic wooden wall.

9. Wannigan Point Cabin #1

Wannigan Point Cabin #1
Taylors Falls
8.0 out of 10, Very good, (3 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.
$321 nightly
The price is $349
Nov 10 - Nov 11
Total with taxes and fees
Wannigan Point Cabin #1
A room with wooden walls, a round table with a white top, wicker chairs, two hanging chairs with cushions, and large windows with greenery outside.

10. Riverside Historic Home near Downtown, Wineries, Hiking

Riverside Historic Home near Downtown, Wineries, Hiking
Taylors Falls
10.0 out of 10, Exceptional, (22 reviews)
"Very smooth and easy stay. Home was well thought out and instructions for everything were very well laid out. "
United States
Elite Motorsports
$543 nightly
The price is $613
Oct 25 - Oct 26
Total with taxes and fees
Riverside Historic Home near Downtown, Wineries, Hiking
A bedroom with a bed, a chair, a small stool, and a window.

11. Cozy 3-bedroom cabin on Cedar Lake

Cozy 3-bedroom cabin on Cedar Lake
Star Prairie
10.0 out of 10, Exceptional, (4 reviews)
"House was clean and close to water. Quiet neighborhood. Host communicated quickly when needed. Look forward to coming back."
United States
grant w.
$463 nightly
The price is $488
Oct 26 - Oct 27
Total with taxes and fees
Cozy 3-bedroom cabin on Cedar Lake
A two-story house with a wooden deck, large windows, and a covered porch area.

12. 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, (11 reviews)
"We loved our stay and only wished we could have stayed longer. Everything in the listing is accurate. Beautiful home."
United States
Angie T.
$398 nightly
The price is $439
Nov 1 - Nov 2
Total with taxes and fees
Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.
A kitchen with wooden cabinets, a granite countertop, a window with a faucet, and a black doormat.

13. Classic Home

Classic Home
Centuria
8.2 out of 10, Very good, (43 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
Oct 26 - Oct 27
Total with taxes and fees
Classic Home
A wooden deck with a view of a lake, outdoor seating, and a building with windows.

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

Nordic Harbor | Room 3 | Arctic Pine - Suite
Center City
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful place and will be staying there again. "
United States
SUZANNE M.
$407 nightly
The price is $448
Oct 18 - Oct 19
Total with taxes and fees
Nordic Harbor | Room 3 | Arctic Pine - Suite
A bedroom with a wooden ceiling, large windows with curtains, a bed with white bedding, and a blanket.

15. Private riverfront cabin with wooded hiking trails

Private riverfront cabin with wooded hiking trails
Amery
9.8 out of 10, Exceptional, (8 reviews)
"What a beautiful getaway… Charming, amazing property , very relaxing, just lovely!"
United States
Chris D.
$367 nightly
The price is $387
Oct 21 - Oct 22
Total with taxes and fees
Private riverfront cabin with wooded hiking trails
Room

16. 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
$228 nightly
The price is $230
Oct 19 - Oct 20
Total with taxes and fees
Gorgeous A-Frame with Panoramic Views, Nestled Atop White Oak Ridge, Wisconsin
A large, historic building with a prominent tower and arched windows, featuring a classic architectural style.

17. Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
Balsam Lake Village
9.0 out of 10, Wonderful, (45 reviews)
"Very clear communication, comfortable beds and all the amenities you need for a night stay!"
United States
Farrah S.
$215 nightly
The price is $227
Nov 8 - Nov 9
Total with taxes and fees
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
A dock with two boats, a wooden deck, and a small outdoor seating area.

18. 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.
$281 nightly
The price is $310
Oct 23 - Oct 24
Total with taxes and fees
Nordic Harbor | Room 5 | Cedar Shadows
A room with a large window overlooking a lake and trees, a round table, and a patterned chair.

19. Apple River Retreat home in Amery

Apple River Retreat home in Amery
Amery
10.0 out of 10, Exceptional, (8 reviews)
"Great last minute find for weekend!"
United States
Dan W.
$218 nightly
The price is $230
Oct 19 - Oct 20
Total with taxes and fees
Apple River Retreat home in Amery
A two-story wooden house with a porch, a stone birdbath, and a brick fire pit.

20. Lake Home property

Lake Home property
Luck
9.2 out of 10, Wonderful, (17 reviews)
"Very nice cozy cabin and such a great, accommodating host! "
United States
Jesse S.
$247 nightly
The price is $261
Oct 19 - Oct 20
Total with taxes and fees
Lake Home property
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

Hudson Inn & Suites

Hudson Inn & Suites

8/10 Good
"Clean place, and quiet even though it was full. I recommend a stay here for the price"
Steve 2-night trip
Posted 15 hours ago
Hudson Inn & Suites

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 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?

Farmington Bottoms State Natural Area and Saint Croix 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.