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
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Osceola vacation rentals

Exterior

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.
$154 nightly
The price is $170
Jul 26 - Jul 27
Total with taxes and fees
Cozy Mother-in-Law Apartment
Interior

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.
$271 nightly
The price is $300
Jul 27 - Jul 28
Total with taxes and fees
Historic 1880s Home
Interior

Apple River Retreat home in Amery

Apple River Retreat home in Amery
Amery
10.0 out of 10, Exceptional, (5 reviews)
"Host was very helpful everythig went perfect we had a great time "
United States
Rusty S.
$232 nightly
The price is $245
Jul 27 - Jul 28
Total with taxes and fees
Apple River Retreat home in Amery
Property grounds

Balsam Lake Sunset Cabin with WiFi & Sauna!

Balsam Lake Sunset Cabin with WiFi & Sauna!
Balsam Lake
9.6 out of 10, Exceptional, (47 reviews)
"I had my out of town family stay here and it was just perfect. It's a great location on the lake, easy to get to both by boat and land."
United States
Kris M.
$1,085 nightly
The price is $1,145
Aug 9 - Aug 10
Total with taxes and fees
Balsam Lake Sunset Cabin with WiFi & Sauna!
Exterior

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, (41 reviews)
"Very clear communication, comfortable beds and all the amenities you need for a night stay!"
United States
Farrah S.
$239 nightly
The price is $252
Aug 2 - Aug 3
Total with taxes and fees
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
3 bedrooms, desk, travel crib, WiFi

Peaceful 3-bedroom cabin in charming Amery

Peaceful 3-bedroom cabin in charming Amery
Amery
10.0 out of 10, Exceptional, (2 reviews)
$412 nightly
The price is $435
Aug 18 - Aug 19
Total with taxes and fees
Peaceful 3-bedroom cabin in charming Amery
Interior

Classic Home

Classic Home
Centuria
8.2 out of 10, Very Good, (38 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
Jul 27 - Jul 28
Total with taxes and fees
Classic Home
Exterior

Lake Home property

Lake Home property
Luck
9.2 out of 10, Wonderful, (15 reviews)
"Very nice cozy cabin and such a great, accommodating host! "
United States
Jesse S.
$313 nightly
The price is $330
Jul 27 - Jul 28
Total with taxes and fees
Lake Home property
Outdoor dining

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
Jul 28 - Jul 29
Total with taxes and fees
Lovers Lookout 2 at Big Rock Creek
Outdoor dining

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.
$181 nightly
The price is $188
Jul 26 - Jul 27
Total with taxes and fees
Lovers Lookout 1: Where Rustic Meets Luxury at Big Rock Creek
Outdoor dining

Romantic Quaint Bell Tent Perfect for a Secluded Couple Escape in Saint Croix Falls, Wisconsin

Romantic Quaint Bell Tent Perfect for a Secluded Couple Escape in Saint Croix Falls, Wisconsin
Saint Croix Falls
$199 nightly
The price is $200
Jul 26 - Jul 27
Total with taxes and fees
Romantic Quaint Bell Tent Perfect for a Secluded Couple Escape in Saint Croix Falls, Wisconsin
Terrace/patio

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
$170 nightly
The price is $177
Jul 27 - Jul 28
Total with taxes and fees
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
WiFi, bed sheets

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.
$215 nightly
The price is $232
Jul 26 - Jul 27
Total with taxes and fees
Wannigan Point Cabin #4
Coffee/tea maker, fridge, microwave, oven

Cambrian & Co. Loft Cozy, Charming, Downtown Ease

Cambrian & Co. Loft Cozy, Charming, Downtown Ease
Taylors Falls
10.0 out of 10, Exceptional, (17 reviews)
"Good place to stay."
United States
Douglas J.
$183 nightly
The price is $197
Jul 30 - Jul 31
Total with taxes and fees
Cambrian & Co. Loft Cozy, Charming, Downtown Ease
Smart TV

Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (42 reviews)
"Cute place. Everything is very comfy including the beds. Great location. The host was very responsive throughout the booking and checking in process. "
United States
Michelle B.
$376 nightly
The price is $414
Aug 17 - Aug 18
Total with taxes and fees
Scandinavian Retreat
Exterior detail

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, (13 reviews)
"Very clean and exactly as described, would stay again! "
United States
Thomas R.
$240 nightly
The price is $265
Aug 2 - Aug 3
Total with taxes and fees
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC
Exterior

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.
$162 nightly
The price is $168
Jul 28 - Jul 29
Total with taxes and fees
Lovers Lookout 3 at Big Rock Creek
Outdoor dining

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
$179 nightly
The price is $180
Jul 28 - Jul 29
Total with taxes and fees
Secluded Waterfront Bell Tent with Picnic Space in Saint Croix Falls, Wisconsin
Property grounds

Incredible Tented Cabin Ideal for Glamping with Fireplace and Barbecue in Saint Croix Falls, Wisconsin

Incredible Tented Cabin Ideal for Glamping with Fireplace and Barbecue in Saint Croix Falls, Wisconsin
Saint Croix Falls
$316 nightly
The price is $333
Aug 18 - Aug 19
Total with taxes and fees
Incredible Tented Cabin Ideal for Glamping with Fireplace and Barbecue in Saint Croix Falls, Wisconsin
Exterior

Creekside Group Glamp Site at Big Rock Creek!

Creekside Group Glamp Site at Big Rock Creek!
Saint Croix Falls
$284 nightly
The price is $294
Jul 27 - Jul 28
Total with taxes and fees
Creekside Group Glamp Site 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

Water Street Inn

Water Street Inn

10/10 Excellent
"Friendly staff on the water of the St. Croix River. My stay was relaxing and enjoyable."
Jamie 2-night trip
Posted 2 hours ago
Water Street Inn

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 $102 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?

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 6 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.