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

Osceola Vacation Rentals

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Our top choices for Osceola vacation rentals

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.
The price is ¥17,819
¥23,085 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Mother-in-Law Apartment

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.
The price is ¥31,542
¥39,632 total
includes taxes & fees
Sep 15 - Sep 16
Historic 1880s Home

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.
The price is ¥20,737
¥30,184 total
includes taxes & fees
Sep 14 - Sep 15
Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm

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.
The price is ¥12,135
¥23,725 total
includes taxes & fees
Sep 14 - Sep 15
Lovers Lookout 2 at Big Rock Creek

5. 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.
The price is ¥34,562
¥69,524 total
includes taxes & fees
Sep 13 - Sep 14
Cozy 3-bedroom cabin on Cedar Lake

6. Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (43 reviews)
"Thanks for a lovely stay!"
United States
Megan J.
The price is ¥29,736
¥60,589 total
includes taxes & fees
Sep 15 - Sep 16
Scandinavian Retreat

7. 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.
The price is ¥12,135
¥23,725 total
includes taxes & fees
Sep 14 - Sep 15
Lovers Lookout 3 at Big Rock Creek

8. 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.
The price is ¥15,207
¥27,129 total
includes taxes & fees
Sep 14 - Sep 15
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge

9. 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.
The price is ¥20,737
¥30,184 total
includes taxes & fees
Sep 24 - Sep 25
Cambrian & Co. Loft Cozy, Charming, Downtown Ease

10. 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.
The price is ¥36,866
¥47,571 total
includes taxes & fees
Sep 16 - Sep 17
Nordic Harbor | Room 5 | Cedar Shadows

11. Classic Home

Classic Home
Centuria
8.0 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
The price is ¥19,201
¥34,843 total
includes taxes & fees
Sep 14 - Sep 15
Classic Home

12. Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very Good, (915 reviews)
"Friendly staff and safe place to stay."
United States
Terry
The price is ¥12,559
¥14,792 total
includes taxes & fees
Sep 14 - Sep 15
Hudson Inn & Suites

13. 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

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
The price is ¥26,092
¥30,144 total
includes taxes & fees
Sep 21 - Sep 22
Gorgeous A-Frame with Panoramic Views, Nestled Atop White Oak Ridge, Wisconsin

15. Huge tent with AC at Big Rock Creek

Huge tent with AC at Big Rock Creek
Saint Croix Falls
The price is ¥15,285
¥31,615 total
includes taxes & fees
Sep 14 - Sep 15
Huge tent with AC at Big Rock Creek

16. 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)
The price is ¥41,475
¥68,286 total
includes taxes & fees
Sep 14 - Sep 15
Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.

17. Private riverfront cabin with wooded hiking trails

Private riverfront cabin with wooded hiking trails
Amery
10.0 out of 10, Exceptional, (2 reviews)
"What a beautiful getaway… Charming, amazing property , very relaxing, just lovely!"
United States
Chris D.
The price is ¥24,857
¥54,078 total
includes taxes & fees
Sep 22 - Sep 23
Private riverfront cabin with wooded hiking trails

18. 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
The price is ¥26,544
¥65,925 total
includes taxes & fees
Sep 15 - Sep 16
Scenic Apple River Retreat - Spacious 4BR Home - Fishing, Tubing & Kayaking

19. 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.
The price is ¥17,834
¥33,078 total
includes taxes & fees
Sep 21 - Sep 22
Apple River Retreat home in Amery

20. Geo Dome at Big Rock Creek!

Geo Dome at Big Rock Creek!
Saint Croix Falls
The price is ¥27,327
¥46,274 total
includes taxes & fees
Sep 15 - Sep 16
Geo Dome at Big Rock Creek!
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

Find out more about Osceola

Search for holiday rentals in Osceola on Expedia! You can easily find your home rentals, villas, holiday apartments in Osceola using one of the methods below:

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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.