Holiday Rentals in Osceola

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Our top choices for Osceola holiday rentals

Cozy Mother-in-Law Apartment

Cozy Mother-in-Law Apartment
Osceola
10.0 out of 10, Exceptional, (50)
"Wonderful stay. So many great features and very clean. Would definitely stay again!"
United States
Nicole A.
The price is €125
includes taxes & fees
8 Jan - 9 Jan 2026
Cozy Mother-in-Law Apartment

Historic 1880s Home

Historic 1880s Home
Osceola
10.0 out of 10, Exceptional, (71)
"The Property was all and more as it was described on VRBO! Very clean, spacious and comfortable for a friend's weekend. Would highly recommend staying here!!"
United States
Debbie C.
The price is €218
includes taxes & fees
11 Jan - 12 Jan 2026
Historic 1880s Home

Home on the Apple River

Home on the Apple River
Amery
10.0 out of 10, Exceptional, (4)
"Great location right on the river. A beautiful view and nice property. Very close to Amery to get supplies and visit nice shopping options. Very comfortable accommodation. Owner was very responsive to any questions. A great value and overall experience. "
United States
Jason D.
The price is €180
includes taxes & fees
5 Jan - 6 Jan 2026
Home on the Apple River

Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very good, (808)
"Great place. Stay there whenever we are in Hudson if they have a room available."
United States
Diana
The price is €78
includes taxes & fees
28 Dec - 29 Dec
Hudson Inn & Suites

Come check out this Cozy 2-bedroom cabin in charming Amery!

Come check out this Cozy 2-bedroom cabin in charming Amery!
Amery
10.0 out of 10, Exceptional, (5)
"Great place to stay. Very clean and comfortable. Host family is very friendly and accommodating."
United States
Susan O.
The price is €209
includes taxes & fees
28 Dec - 29 Dec
Come check out this Cozy 2-bedroom cabin in charming Amery!

Eleanor - 2 bdr Cabin unit on River w/SUPS, Kayaks, & paddle boat. Pet friendly!

Eleanor - 2 bdr Cabin unit on River w/SUPS, Kayaks, & paddle boat. Pet friendly!
Amery
9.6 out of 10, Exceptional, (14)
"The Eleanor is a a pretty, cozy, well-appointed dwelling with a shabby-chic cottage ambience. We stayed one night, after attending a wedding at the Shed, but would have been happy to stay for a long weekend, to explore the countryside around Amery. Winter or summer, this is the perfect place for a family retreat!"
United States
Jennifer K.
The price is €188
includes taxes & fees
5 Jan - 6 Jan 2026
Eleanor - 2 bdr Cabin unit on River w/SUPS, Kayaks, & paddle boat. Pet friendly!

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
9.2 out of 10, Wonderful, (34)
"Lovely, cozy house. We enjoyed our stay!"
United States
Geoff P.
The price is €189
includes taxes & fees
29 Dec - 30 Dec
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

1 Bdr Cabin unit Respite on Apple River. Kayaks, SUPs, and more! Pet friendly!

1 Bdr Cabin unit Respite on Apple River. Kayaks, SUPs, and more! Pet friendly!
Amery
9.8 out of 10, Exceptional, (14)
"We very much enjoyed our stay at this peaceful quaint cabin. We would definitely recommend."
United States
Deb C.
The price is €193
includes taxes & fees
25 Jan - 26 Jan 2026
1 Bdr Cabin unit Respite on Apple River. Kayaks, SUPs, and more! Pet friendly!

Romantic getaway! With gorgeous views from the Hot Tub!

Romantic getaway! With gorgeous views from the Hot Tub!
Taylors Falls
9.4 out of 10, Exceptional, (103)
"This place was great, only down fall was no sink ( just in bathroom) and didnt realize there was no stove/oven and no toaster."
United States
Dawn N.
The price is €234
includes taxes & fees
27 Dec - 28 Dec
Romantic getaway! With gorgeous views from the Hot Tub!

Reflections Retreat on Lake Magnor in Clayton, WI with beautiful lake view

Reflections Retreat on Lake Magnor in Clayton, WI with beautiful lake view
Clayton
10.0 out of 10, Exceptional, (5)
"This was a wonderful time of relaxation!"
United States
Sean H.
Reflections Retreat on Lake Magnor in Clayton, WI with beautiful lake view

Minne-GetAway: Modern Cottage

Minne-GetAway: Modern Cottage
North Saint Paul
9.6 out of 10, Exceptional, (14)
"Comfortable beds and clean bathrooms."
United States
Angelika
The price is €224
includes taxes & fees
5 Jan - 6 Jan 2026
Minne-GetAway: Modern Cottage

Woodsy Retreat: Chef's Kitchen, Dance Room & Gym

Woodsy Retreat: Chef's Kitchen, Dance Room & Gym
2.0 star property
White Bear Lake
10.0 out of 10, Exceptional, (5)
"Great kitchen, terrific bathrooms, and nice bedrooms with comfortable beds. The host is responsive and dedicated to making sure your experience staying at the house is as good as it can be. Highly recommend."
United States
Jeff J.
The price is €313
includes taxes & fees
28 Dec - 29 Dec
Woodsy Retreat: Chef's Kitchen, Dance Room & Gym

Private Suite in historic Stillwater North Hill

Private Suite in historic Stillwater North Hill
Stillwater
9.8 out of 10, Exceptional, (30)
"The hosts and place were fantastic all around! "
United States
Tabitha B.
The price is €187
includes taxes & fees
25 Jan - 26 Jan 2026
Private Suite in historic Stillwater North Hill

Wannigan Point Cabin #4

Wannigan Point Cabin #4
Taylors Falls
10.0 out of 10, Exceptional, (1)
"This was a great location and a lovely cabin. However, when we used the oven there was a strong smell. Other than that, we had a wonderful time. Thank you."
United States
michelle b.
The price is €262
includes taxes & fees
27 Dec - 28 Dec
Wannigan Point Cabin #4

Classic Home

Classic Home
Centuria
8.4 out of 10, Very good, (36)
"comfortable, clean"
United States
Heather R.
Classic Home

Walking distance to public beach, boat landing, and downtown Balsam Lake

Walking distance to public beach, boat landing, and downtown Balsam Lake
Balsam Lake Village
10.0 out of 10, Exceptional, (1)
"The property was very spacious and comfortable. It was well stocked with pots and pans so we were able to cook. Location was great, Overall it was a great stay."
United States
Nancy A.
The price is €170
includes taxes & fees
26 Dec - 27 Dec
Walking distance to public beach, boat landing, and downtown Balsam Lake

Lake Home property

Lake Home property
Luck
9.6 out of 10, Exceptional, (12)
"The place is more of a home than a cabin. Simply beautiful, cozy and comfortable "
United States
Cathy
The price is €247
includes taxes & fees
6 Jan - 7 Jan 2026
Lake Home property

River road cabin

River road cabin
Saint Croix Falls
8.0 out of 10, Very good, (14)
"Great stay. Would do it again."
United States
Jeff W.
The price is €179
includes taxes & fees
28 Dec - 29 Dec
River road cabin

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
9.8 out of 10, Exceptional, (9)
"Very clean and exactly as described, would stay again! "
United States
Thomas R.
The price is €198
includes taxes & fees
31 Dec - 1 Jan 2026
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC

Who knew "Up North" could be so close to home!

Who knew "Up North" could be so close to home!
Saint Croix Falls
9.8 out of 10, Exceptional, (41)
"We enjoyed our stay so much! There is a lot to do around the area and our cabin was cozy & relaxing. Thank you!"
United States
Pwggy D.
The price is €251
includes taxes & fees
8 Jan - 9 Jan 2026
Who knew "Up North" could be so close to home!
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

Everything you need to know about Osceola holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osceola holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Osceola holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osceola holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osceola holiday rentals we have selected for you start as low as €78 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Osceola rentals

At Expedia, we put the best Osceola holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Osceola?

Yes, there are holiday rentals in Osceola close to Osceola & St. Croix Valley Railway, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Osceola has to offer?

Historic Stillwater Home close to downtown: This holiday home rental outside of Osceola offers a patio, a private garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Osceola?

Choose from 6 Expedia holiday rentals in Osceola for a memorable holiday.

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 holiday rentals like in Osceola?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osceola. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.