Osceola Holiday Rentals

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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)
"Wonderful stay. So many great features and very clean. Would definitely stay again!"
United States
Nicole A.
The price is NZ$224
includes taxes & fees
26 Jan - 27 Jan
Cozy Mother-in-Law Apartment

Historic 1880s Home

Historic 1880s Home
Osceola
10.0 out of 10, Exceptional, (72 reviews)
"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.
The price is NZ$411
includes taxes & fees
22 Feb - 23 Feb
Historic 1880s Home

Home on the Apple River

Home on the Apple River
Amery
10.0 out of 10, Exceptional, (4 reviews)
"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 NZ$347
includes taxes & fees
26 Jan - 27 Jan
Home on the Apple River

Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very good, (812 reviews)
"Clean room and very quiet!"
United States
Maureen
The price is NZ$155
includes taxes & fees
26 Jan - 27 Jan
Hudson Inn & Suites

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, (6 reviews)
"The house was great. Clean. Loved the bathroom. Everything we needed for our stay and more"
United States
Rhoda O.
The price is NZ$572
includes taxes & fees
26 Jan - 27 Jan
Woodsy Retreat: Chef's Kitchen, Dance Room & Gym

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 reviews)
"Great place to stay. Very clean and comfortable. Host family is very friendly and accommodating."
United States
Susan O.
The price is NZ$407
includes taxes & fees
4 Feb - 5 Feb
Come check out this Cozy 2-bedroom cabin in charming Amery!

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 NZ$365
includes taxes & fees
24 Jan - 25 Jan
Wannigan Point Cabin #5

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)
"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 NZ$359
includes taxes & fees
26 Jan - 27 Jan
Eleanor - 2 bdr Cabin unit on River w/SUPS, Kayaks, & paddle boat. Pet friendly!

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 reviews)
"It’s was clean and modern. We enjoyed our stay "
United States
Derek K.
The price is NZ$172
includes taxes & fees
28 Jan - 29 Jan
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 NZ$439
includes taxes & fees
4 Feb - 5 Feb
Minne-GetAway: Modern Cottage

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, (104 reviews)
"Great value! I would stay again."
United States
Matt C.
The price is NZ$464
includes taxes & fees
12 Feb - 13 Feb
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)
"Lovely, cozy house. We enjoyed our stay!"
United States
Geoff P.
The price is NZ$310
includes taxes & fees
26 Jan - 27 Jan
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

Lake Home property

Lake Home property
Luck
9.6 out of 10, Exceptional, (13 reviews)
"The place is more of a home than a cabin. Simply beautiful, cozy and comfortable "
United States
Cathy
The price is NZ$425
includes taxes & fees
26 Jan - 27 Jan
Lake Home property

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 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 NZ$425
includes taxes & fees
18 Feb - 19 Feb
Who knew "Up North" could be so close to home!

Private Suite in historic Stillwater North Hill

Private Suite in historic Stillwater North Hill
Stillwater
10.0 out of 10, Exceptional, (32 reviews)
"The hosts and place were fantastic all around! "
United States
Tabitha B.
The price is NZ$367
includes taxes & fees
26 Jan - 27 Jan
Private Suite in historic Stillwater North Hill

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, (2 reviews)
"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 NZ$524
includes taxes & fees
24 Jan - 25 Jan
Walking distance to public beach, boat landing, and downtown Balsam Lake

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 NZ$305
includes taxes & fees
26 Jan - 27 Jan
River road cabin

LumberJill Lodge #3 | Deluxe King Room

LumberJill Lodge #3 | Deluxe King Room
Balsam Lake Village
The price is NZ$319
includes taxes & fees
24 Jan - 25 Jan
LumberJill Lodge #3 | Deluxe King Room

Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (35 reviews)
"The property was so clean and beautifully decorated. Thoughtful hosts and lovely community. "
United States
Hollie A.
The price is NZ$591
includes taxes & fees
25 Jan - 26 Jan
Scandinavian Retreat

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 reviews)
"Very clean and exactly as described, would stay again! "
United States
Thomas R.
The price is NZ$378
includes taxes & fees
5 Feb - 6 Feb
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

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, 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 NZ$155 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?

Just steps to Downtown Hudson and St. Croix River! : This holiday home rental outside of Osceola is located on a river, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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?

Farmington Bottoms State Natural Area and Saint Croix 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.