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, (51 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 €119
includes taxes & fees
31 Mar - 1 Apr
Cozy Mother-in-Law Apartment

Historic 1880s Home

Historic 1880s Home
Osceola
10.0 out of 10, Exceptional, (73 reviews)
"Beautiful home and beautiful vibe. Would visit again!"
United States
Janice
The price is €185
includes taxes & fees
30 Mar - 31 Mar
Historic 1880s Home

Home on the Apple River

Home on the Apple River
Amery
10.0 out of 10, Exceptional, (4 reviews)
"Host was very helpful everythig went perfect we had a great time "
United States
Rusty S.
The price is €177
includes taxes & fees
30 Mar - 31 Mar
Home on the Apple River

Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very good, (817 reviews)
"Great place. Stay there whenever we are in Hudson if they have a room available."
United States
Diana
The price is €79
includes taxes & fees
29 Mar - 30 Mar
Hudson Inn & Suites

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, (105 reviews)
"BEST HOT TUB EVER. Comfortable beds and living room area, nicely set up for food prep, given that there's not a full kitchen. "
United States
MaryBeth S.
The price is €234
includes taxes & fees
3 Apr - 4 Apr
Romantic getaway! With gorgeous views from the Hot Tub!

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, (35 reviews)
"Very clear communication, comfortable beds and all the amenities you need for a night stay!"
United States
Farrah S.
The price is €162
includes taxes & fees
31 Mar - 1 Apr
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, (16 reviews)
"It’s was clean and modern. We enjoyed our stay "
United States
Derek K.
The price is €159
includes taxes & fees
29 Mar - 30 Mar
1 Bdr Cabin unit Respite on Apple River. Kayaks, SUPs, and more! Pet friendly!

Minne-GetAway: Modern Cottage

Minne-GetAway: Modern Cottage
North Saint Paul
9.6 out of 10, Exceptional, (14 reviews)
"Comfortable beds and clean bathrooms."
United States
Angelika
The price is €289
includes taxes & fees
24 Apr - 25 Apr
Minne-GetAway: Modern Cottage

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

Woodsy Retreat: Chef's Kitchen, Dance Room & Gym
White Bear Lake
10.0 out of 10, Exceptional, (7 reviews)
"Fantastic home with ample kitchen space and everything you need to prepare meals. Has a great layout and amenities for entertaining. We thoroughly enjoyed our stay and would visit again!"
United States
Drew R.
The price is €293
includes taxes & fees
30 Mar - 31 Mar
Woodsy Retreat: Chef's Kitchen, Dance Room & Gym

Private Suite in historic Stillwater North Hill

Private Suite in historic Stillwater North Hill
Stillwater
10.0 out of 10, Exceptional, (33 reviews)
"The hosts and place were fantastic all around! "
United States
Tabitha B.
The price is €198
includes taxes & fees
29 Mar - 30 Mar
Private Suite in historic Stillwater North Hill

River road cabin

River road cabin
Saint Croix Falls
8.0 out of 10, Very good, (14 reviews)
"Great stay. Would do it again."
United States
Jeff W.
The price is €157
includes taxes & fees
30 Mar - 31 Mar
River road cabin

Peaceful 3-bedroom cabin in charming Amery

Peaceful 3-bedroom cabin in charming Amery
Amery
Peaceful 3-bedroom cabin in charming Amery

Where Comfort Meets Adventure — In Every Season!

Where Comfort Meets Adventure — In Every Season!
Saint Croix Falls
9.8 out of 10, Exceptional, (41 reviews)
"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 €234
includes taxes & fees
29 Mar - 30 Mar
Where Comfort Meets Adventure — In Every Season!

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, (15 reviews)
"Very clean, comfortable cabin, beautiful area, nice fire pit area, love the large soaking tub! "
United States
Deb P.
The price is €185
includes taxes & fees
29 Mar - 30 Mar
Eleanor - 2 bdr Cabin unit on River w/SUPS, Kayaks, & paddle boat. Pet friendly!

Historic Stillwater Home close to downtown

Historic Stillwater Home close to downtown
Stillwater
10.0 out of 10, Exceptional, (69 reviews)
"Very walkable distance from downtown. We loved our stay and appreciated all the sweet touches and amenities!"
United States
Allyssa M.
The price is €287
includes taxes & fees
29 Mar - 30 Mar
Historic Stillwater Home close to downtown

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 reviews)
"Was great hosted and very nice place."
United States
Jennifer w.
The price is €279
includes taxes & fees
28 Mar - 29 Mar
Reflections Retreat on Lake Magnor in Clayton, WI with beautiful lake view

Nordic Harbor | Room 4 | Nordic Spruce

Nordic Harbor | Room 4 | Nordic Spruce
Center City
The price is €266
includes taxes & fees
8 Apr - 9 Apr
Nordic Harbor | Room 4 | Nordic Spruce

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, (3 reviews)
"Excellent Place to Stay. Perfect for a Small Get-away. "
United States
Zac D.
The price is €266
includes taxes & fees
29 Mar - 30 Mar
Walking distance to public beach, boat landing, and downtown Balsam Lake

Luxurious remodel near historic downtown Hudson!

Luxurious remodel near historic downtown Hudson!
Hudson
10.0 out of 10, Exceptional, (30 reviews)
"Perfect for a girls get away! "
United States
Anne D.
Luxurious remodel near historic downtown Hudson!

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 €213
includes taxes & fees
6 Apr - 7 Apr
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
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 €79 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?

Stillwater's Third Street Inn: This holiday home rental outside of Osceola offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Osceola?

Choose from 5 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.