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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

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.
The price is AED 456
AED 585 total
includes taxes & fees
11 Aug - 12 Aug
Cozy Mother-in-Law Apartment
Interior

2. Historic 1880s Home

Historic 1880s Home
Osceola
10.0 out of 10, Exceptional, (79 reviews)
"Great spot to stay for the weekend. Close proximity to downtown. "
United States
Connie S.
The price is AED 793
AED 998 total
includes taxes & fees
11 Aug - 12 Aug
Historic 1880s Home
Private kitchen

3. 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.
The price is AED 413
AED 845 total
includes taxes & fees
9 Aug - 10 Aug
Wannigan Point Cabin #2
Smart TV, fireplace

4. 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.
The price is AED 496
AED 722 total
includes taxes & fees
18 Aug - 19 Aug
Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
Outdoor dining

5. 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 AED 290
AED 567 total
includes taxes & fees
1 Sep - 2 Sep
Lovers Lookout 2 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.
The price is AED 734
AED 1,490 total
includes taxes & fees
18 Aug - 19 Aug
Scandinavian Retreat
Exterior

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 AED 371
AED 656 total
includes taxes & fees
12 Aug - 13 Aug
Lovers Lookout 3 at Big Rock Creek
Terrace/patio

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
The price is AED 364
AED 649 total
includes taxes & fees
10 Aug - 11 Aug
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
Coffee/tea maker, fridge, microwave, oven

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

Cambrian & Co. Loft Cozy, Charming, Downtown Ease
Taylors Falls
10.0 out of 10, Exceptional, (20 reviews)
"Good place to stay."
United States
Douglas J.
The price is AED 496
AED 718 total
includes taxes & fees
9 Aug - 10 Aug
Cambrian & Co. Loft Cozy, Charming, Downtown Ease
WiFi, bed sheets

10. Wannigan Point Cabin #4

Wannigan Point Cabin #4
Taylors Falls
10.0 out of 10, Exceptional, (2 reviews)
"Everything was as expected- very clean and well maintained. "
United States
Breanne B.
The price is AED 413
AED 845 total
includes taxes & fees
9 Aug - 10 Aug
Wannigan Point Cabin #4
Property grounds

11. 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 AED 882
AED 1,130 total
includes taxes & fees
16 Aug - 17 Aug
Nordic Harbor | Room 5 | Cedar Shadows
Interior

12. Wannigan Point Cabin #5

Wannigan Point Cabin #5
Taylors Falls
7.4 out of 10, Good, (3 reviews)
"Very cute and comfy cabin! It was the perfect location for us as we were in town for Hay Days. "
United States
Deanna N.
The price is AED 413
AED 845 total
includes taxes & fees
9 Aug - 10 Aug
Wannigan Point Cabin #5
Private kitchen

13. Wannigan Point Cabin #3

Wannigan Point Cabin #3
Taylors Falls
8.0 out of 10, Very Good, (2 reviews)
"Very nice and clean cabin with plenty of room to move around. Since it was cool outside, the wood stove made for a cozy atmosphere."
United States
Lisa M.
The price is AED 413
AED 849 total
includes taxes & fees
12 Aug - 13 Aug
Wannigan Point Cabin #3
1 bedroom, WiFi, bed sheets

14. Secluded Waterfront Bell Tent with Picnic Space in Saint Croix Falls, Wisconsin

Secluded Waterfront Bell Tent with Picnic Space in Saint Croix Falls, Wisconsin
Saint Croix Falls
The price is AED 610
AED 699 total
includes taxes & fees
12 Aug - 13 Aug
Secluded Waterfront Bell Tent with Picnic Space in Saint Croix Falls, Wisconsin
Interior

15. 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
The price is AED 459
AED 833 total
includes taxes & fees
11 Aug - 12 Aug
Classic Home
Desk, iron/ironing board, WiFi (free), bed sheets

16. Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very Good, (881 reviews)
"Older hotel but well maintained and great value for the price."
United States
Dennis
The price is AED 300
AED 354 total
includes taxes & fees
9 Aug - 10 Aug
Hudson Inn & Suites
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, (5 reviews)
The price is AED 992
AED 1,645 total
includes taxes & fees
12 Aug - 13 Aug
Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.
Terrace/patio

18. 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 AED 642
AED 735 total
includes taxes & fees
24 Aug - 25 Aug
Gorgeous A-Frame with Panoramic Views, Nestled Atop White Oak Ridge, Wisconsin
Interior

19. Wannigan Point Cabin #1

Wannigan Point Cabin #1
Taylors Falls
7.0 out of 10, Good, (2 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.
The price is AED 459
AED 907 total
includes taxes & fees
13 Aug - 14 Aug
Wannigan Point Cabin #1
Exterior detail

20. 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, (14 reviews)
"Very clean and exactly as described, would stay again! "
United States
Thomas R.
The price is AED 602
AED 876 total
includes taxes & fees
17 Aug - 18 Aug
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC
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
"I enjoyed a very comfortable stay at the Water Street Inn. The hotel accommodated my request for a disability room with a walk-in shower. This was very helpful for my personal safety and I appreciated their hospitality. My room also had a nice view of the St. Croix river. The restaurant staff members: Chrissy, Deb, Gianna and John were always gracious and accommodating with my menu requests. After a few days the staff at Charlie's were like family. The outside terrace has wonderful view of the river all day long to enjoy your dining experiences. I recommend the Water Street Inn."
Thomas 5-night trip
Posted 1 day ago
Water Street Inn

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?

MINNeSTAY* St. Croix Valley Inn: This highly rated vacation home rental in Osceola is located on the waterfront and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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.