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 AU$187
includes taxes & fees
16 Feb - 17 Feb
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 AU$319
includes taxes & fees
15 Feb - 16 Feb
Historic 1880s Home

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 was very clean, relaxing and had everything we needed. We enjoyed our stay and the grounds had kayaks for us to get out on the lake. We definitely recommend staying here."
United States
Jayme W.
The price is AU$300
includes taxes & fees
16 Feb - 17 Feb
Eleanor - 2 bdr Cabin unit on River w/SUPS, Kayaks, & paddle boat. Pet friendly!

Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very good, (814 reviews)
"It was clean and staff persons were polite and professional."
United States
Michael
The price is AU$125
includes taxes & fees
15 Feb - 16 Feb
Hudson Inn & Suites

LumberJill Lodge #3 | Deluxe King Room

LumberJill Lodge #3 | Deluxe King Room
Balsam Lake Village
The price is AU$247
includes taxes & fees
18 Feb - 19 Feb
LumberJill Lodge #3 | Deluxe King Room

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, (15 reviews)
"It’s was clean and modern. We enjoyed our stay "
United States
Derek K.
The price is AU$274
includes taxes & fees
15 Mar - 16 Mar
1 Bdr Cabin unit Respite on Apple River. Kayaks, SUPs, and more! Pet friendly!

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 AU$354
includes taxes & fees
17 Feb - 18 Feb
Lake Home property

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 AU$385
includes taxes & fees
13 Mar - 14 Mar
Romantic getaway! With gorgeous views from the Hot Tub!

Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (36 reviews)
"The property was so clean and beautifully decorated. Thoughtful hosts and lovely community. "
United States
Hollie A.
The price is AU$527
includes taxes & fees
15 Feb - 16 Feb
Scandinavian Retreat

Relaxing Townhouse Escape

Relaxing Townhouse Escape
Hugo
8.8 out of 10, Excellent, (16 reviews)
"Nice location "
United States
Mary O.
The price is AU$349
includes taxes & fees
16 Feb - 17 Feb
Relaxing Townhouse Escape

Nordic Harbor | Room 1 | Acorn Oak

Nordic Harbor | Room 1 | Acorn Oak
Center City
10.0 out of 10, Exceptional, (2 reviews)
"Our stay was wonderful---quaint, modern-rustic and very comfortable. We loved being able to walk across the parking lot to the rooftop bar."
United States
Alisha H.
The price is AU$436
includes taxes & fees
13 Feb - 14 Feb
Nordic Harbor | Room 1 | Acorn Oak

Wannigan Point Cabin #4

Wannigan Point Cabin #4
Taylors Falls
10.0 out of 10, Exceptional, (1 review)
"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 AU$366
includes taxes & fees
20 Feb - 21 Feb
Wannigan Point Cabin #4

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 AU$324
includes taxes & fees
13 Feb - 14 Feb
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC

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)
"The house was great. Clean. Loved the bathroom. Everything we needed for our stay and more"
United States
Rhoda O.
The price is AU$485
includes taxes & fees
16 Feb - 17 Feb
Woodsy Retreat: Chef's Kitchen, Dance Room & Gym

Historic Stillwater Home close to downtown

Historic Stillwater Home close to downtown
Stillwater
10.0 out of 10, Exceptional, (65 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 AU$480
includes taxes & fees
17 Feb - 18 Feb
Historic Stillwater Home close to downtown

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 AU$358
includes taxes & fees
25 Feb - 26 Feb
Minne-GetAway: Modern Cottage

BestLocation|Romantic|ViewBridgeFromBed|Couples|Pets|Photo backdrop|Nightlife!!!

BestLocation|Romantic|ViewBridgeFromBed|Couples|Pets|Photo backdrop|Nightlife!!!
Stillwater
9.4 out of 10, Exceptional, (59 reviews)
"Enjoyed our stay in stillwater. Host is very responsive and the property is amazing. The location is perfect for a getaway. We have enjoyed the property before and plan too again "
United States
Michael M.
The price is AU$522
includes taxes & fees
16 Feb - 17 Feb
BestLocation|Romantic|ViewBridgeFromBed|Couples|Pets|Photo backdrop|Nightlife!!!

LumberJill Lodge #6 | King Room

LumberJill Lodge #6 | King Room
Balsam Lake Village
The price is AU$249
includes taxes & fees
21 Feb - 22 Feb
LumberJill Lodge #6 | King Room

Historic Swedish Cottage on Quiet Lindstrom Lake

Historic Swedish Cottage on Quiet Lindstrom Lake
Lindstrom
9.4 out of 10, Exceptional, (237 reviews)
"Beautiful property. Plenty of space."
United States
Colin J.
The price is AU$880
includes taxes & fees
22 Feb - 23 Feb
Historic Swedish Cottage on Quiet Lindstrom Lake

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 AU$325
includes taxes & fees
19 Feb - 20 Feb
Private Suite in historic Stillwater North Hill
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 favourite 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 depend 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 AU$125 per night. Entering your travel dates in the search wizard might find you 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?

Gathering families, friends, & coworkers: This holiday home rental outside of Osceola is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 16 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 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.