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Osceola Vacation Rentals

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In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Osceola vacation rentals

Exterior
Cozy Mother-in-Law Apartment

Apartment in Osceola

Cozy Mother-in-Law Apartment
10.0 out of 10, Exceptional, (50)
"Wonderful stay. So many great features and very clean. Would definitely stay again!"
United States
Nicole A.
$118 nightly
The price is $131
Jan 10 - Jan 11
Total with taxes and fees
Cozy Mother-in-Law Apartment
Interior
Historic 1880s Home

Vacation Home in Osceola

Historic 1880s Home
10.0 out of 10, Exceptional, (71)
"This is a beautiful home very close to downtown and restaurants. The host did an amazing job! We would love to stay here again! "
United States
Kristine R.
$205 nightly
The price is $227
Jan 18 - Jan 19
Total with taxes and fees
Historic 1880s Home
Living area
Home on the Apple River

Mobile Home in Amery

Home on the Apple River
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.
$195 nightly
The price is $206
Jan 12 - Jan 13
Total with taxes and fees
Home on the Apple River
Desk, iron/ironing board, free WiFi, bed sheets
Hudson Inn & Suites

Aparthotel in Hudson

Hudson Inn & Suites
3.0 star property
8.2 out of 10, Very Good, (810)
"Great place. Stay there whenever we are in Hudson if they have a room available."
United States
Diana
$85 nightly
The price is $92
Jan 11 - Jan 12
Total with taxes and fees
Hudson Inn & Suites
Private kitchen
Wannigan Point Cabin #2

Cabin in Taylors Falls

Wannigan Point Cabin #2
10.0 out of 10, Exceptional, (2)
"These cabins are a great place to stay while visiting the Taylors Falls area. They are centrally located but feels like you are further out than you are. We enjoyed having a small kitchen and a private place to stay with outdoor seating and fire pit."
United States
Wendy A.
$198 nightly
The price is $214
Jan 9 - Jan 10
Total with taxes and fees
Wannigan Point Cabin #2
Dining
1 Bdr Cabin unit Respite on Apple River. Kayaks, SUPs, and more! Pet friendly!

Cabin in Amery

1 Bdr Cabin unit Respite on Apple River. Kayaks, SUPs, and more! Pet friendly!
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.
$91 nightly
The price is $101
Jan 14 - Jan 15
Total with taxes and fees
1 Bdr Cabin unit Respite on Apple River. Kayaks, SUPs, and more! Pet friendly!
Terrace/patio
Private Suite in historic Stillwater North Hill

Apartment in Stillwater

Private Suite in historic Stillwater North Hill
10.0 out of 10, Exceptional, (32)
"The hosts and place were fantastic all around! "
United States
Tabitha B.
$198 nightly
The price is $216
Jan 12 - Jan 13
Total with taxes and fees
Private Suite in historic Stillwater North Hill
Exterior
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

Vacation Home in Balsam Lake Village

Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
9.2 out of 10, Wonderful, (35)
"Lovely, cozy house. We enjoyed our stay!"
United States
Geoff P.
$176 nightly
The price is $186
Jan 12 - Jan 13
Total with taxes and fees
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
Dining
Eleanor - 2 bdr Cabin unit on River w/SUPS, Kayaks, & paddle boat. Pet friendly!

Cabin in Amery

Eleanor - 2 bdr Cabin unit on River w/SUPS, Kayaks, & paddle boat. Pet friendly!
9.6 out of 10, Exceptional, (15)
"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.
$195 nightly
The price is $215
Jan 11 - Jan 12
Total with taxes and fees
Eleanor - 2 bdr Cabin unit on River w/SUPS, Kayaks, & paddle boat. Pet friendly!
Exterior
Romantic getaway! With gorgeous views from the Hot Tub!

Apartment in Taylors Falls

Romantic getaway! With gorgeous views from the Hot Tub!
9.4 out of 10, Exceptional, (103)
"Great value! I would stay again."
United States
Matt C.
$245 nightly
The price is $263
Feb 8 - Feb 9
Total with taxes and fees
Romantic getaway! With gorgeous views from the Hot Tub!
Smart TV
Minne-GetAway: Modern Cottage

Vacation Home in North Saint Paul

Minne-GetAway: Modern Cottage
9.6 out of 10, Exceptional, (14)
"Comfortable beds and clean bathrooms."
United States
Angelika
$238 nightly
The price is $258
Jan 12 - Jan 13
Total with taxes and fees
Minne-GetAway: Modern Cottage
Exterior
Lake Home property

Cabin in Luck

Lake Home property
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
$240 nightly
The price is $253
Jan 12 - Jan 13
Total with taxes and fees
Lake Home property
Interior
Classic Home

Vacation Home in Centuria

Classic Home
8.4 out of 10, Very Good, (36)
"comfortable, clean"
United States
Heather R.
$199 nightly
The price is $210
Jan 9 - Jan 10
Total with taxes and fees
Classic Home
Interior
Come check out this Cozy 2-bedroom cabin in charming Amery!

Cabin in Amery

Come check out this Cozy 2-bedroom cabin in charming 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.
$229 nightly
The price is $242
Jan 9 - Jan 10
Total with taxes and fees
Come check out this Cozy 2-bedroom cabin in charming Amery!
Interior
Woodsy Retreat: Chef's Kitchen, Dance Room & Gym

Vacation Home in White Bear Lake

Woodsy Retreat: Chef's Kitchen, Dance Room & Gym
2.0 star property
10.0 out of 10, Exceptional, (6)
"The house was great. Clean. Loved the bathroom. Everything we needed for our stay and more"
United States
Rhoda O.
Woodsy Retreat: Chef's Kitchen, Dance Room & Gym
Exterior
River road cabin

Cabin in Saint Croix Falls

River road cabin
8.0 out of 10, Very Good, (14)
"Great stay. Would do it again."
United States
Jeff W.
$171 nightly
The price is $180
Jan 12 - Jan 13
Total with taxes and fees
River road cabin
Smart TV, DVD player, books, video library
Reflections Retreat on Lake Magnor in Clayton, WI with beautiful lake view

Vacation Home in Clayton

Reflections Retreat on Lake Magnor in Clayton, WI with beautiful lake view
10.0 out of 10, Exceptional, (5)
"This was a wonderful time of relaxation!"
United States
Sean H.
$335 nightly
The price is $353
Jan 10 - Jan 11
Total with taxes and fees
Reflections Retreat on Lake Magnor in Clayton, WI with beautiful lake view
Exterior
Who knew "Up North" could be so close to home!

Cabin in Saint Croix Falls

Who knew "Up North" could be so close to home!
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.
$273 nightly
The price is $289
Jan 15 - Jan 16
Total with taxes and fees
Who knew "Up North" could be so close to home!
Living area
Walking distance to public beach, boat landing, and downtown Balsam Lake

Vacation Home in Balsam Lake Village

Walking distance to public beach, boat landing, and downtown Balsam Lake
10.0 out of 10, Exceptional, (2)
"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.
$186 nightly
The price is $196
Jan 9 - Jan 10
Total with taxes and fees
Walking distance to public beach, boat landing, and downtown Balsam Lake
Fridge, microwave, oven, stovetop
CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails

Vacation Home in Stillwater

CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails
10.0 out of 10, Exceptional, (1)
"What a perfect place to stay!!! The hot tub was wonderful and the house was clean and comfortable. The bunkbed room was perfect for the kiddos and the master bedroom has the best mattress I have ever slept on. Highly recommend to anyone wanting to stay in Stillwater. "
United States
Maggie L.
$629 nightly
The price is $685
Jan 11 - Jan 12
Total with taxes and fees
CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails
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

Hotel Crosby

Hotel Crosby

10/10 Excellent
"Great stay"
Tashi 1-night trip
Posted 3 days ago
Hotel Crosby

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 $92 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?

The Pine House: a cozy home for you & yours!: This vacation home rental outside of Osceola offers a patio, an arcade game room, and a barbecue grill 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 you can cook with friends or family.

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.