Photo by rinchindorj

Osceola Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Osceola

Historic 1880s Home

10.0 out of 10, Exceptional, (65)
"We stayed here for just one night as we were in town for a family wedding. The communication leading up to the stay with Allison was great, the check-in process easy, the home was clean and the beds comfortable. I would definitely stay here again if in the area."
The price is AU$320
includes taxes & fees
23 Sept - 24 Sept
Historic 1880s Home

Hudson Inn & Suites

3.0 star property
8.2 out of 10, Very good, (777)
"The property was perfect for our short stay."
The price is AU$143
includes taxes & fees
23 Sept - 24 Sept
Hudson Inn & Suites

Gathering families, friends, & coworkers

9.8 out of 10, Exceptional, (37)
"This was an amazing property for our large family to gather together to celebrate Christmas. There was plenty of sleeping, dining and gathering space."
Gathering families, friends, & coworkers

Sleepy Deer Chalet! Spacious, Well-Appointed home on Beautiful Lake Wapogasset!

10.0 out of 10, Exceptional, (26)
"We had an awesome stay! Great layout and beautiful outdoor areas."
Sleepy Deer Chalet! Spacious, Well-Appointed home on Beautiful Lake Wapogasset!

Get away from it all and relax on the lake!

9.8 out of 10, Exceptional, (177)
"We are return guests. The cabin was clean, comfortable and in a beautiful location! The king bed is fantastic.We look forward to our next stay. Thank you Mary Beth."
Get away from it all and relax on the lake!

All seasons cabin getaway

10.0 out of 10, Exceptional, (51)
"Very clean and had everything we needed. Lot's of room for a bigger group. Paddle boards were excellent. It is nice having the island to block the wake board waves from the docks as well. Walking distance to downtown!"
All seasons cabin getaway

Romantic getaway! With gorgeous views from the Hot Tub!

9.4 out of 10, Exceptional, (98)
"Very clean & tidy. Cute space below the residence home, a finished 2 bed full bath basement apartment with plenty of extras. Thanx JP"
The price is AU$404
includes taxes & fees
23 Sept - 24 Sept
Romantic getaway! With gorgeous views from the Hot Tub!

Historic Swedish Cottage on Quiet Lindstrom Lake

9.4 out of 10, Exceptional, (224)
"beautiful property and great stay for 4 families with kids. Very friendly and helpful host!"
The price is AU$1,130
includes taxes & fees
23 Sept - 24 Sept
Historic Swedish Cottage on Quiet Lindstrom Lake

Lake Home property

10.0 out of 10, Exceptional, (9)
"Girls getaway was perfect. Hard to find restaurants nearby open that were not bars. "
The price is AU$436
includes taxes & fees
23 Sept - 24 Sept
Lake Home property

Private Suite in historic Stillwater North Hill

10.0 out of 10, Exceptional, (26)
"Highly recommend staying here"
The price is AU$367
includes taxes & fees
23 Sept - 24 Sept
Private Suite in historic Stillwater North Hill

Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

9.2 out of 10, Wonderful, (33)
"Lovely, cozy house. We enjoyed our stay!"
The price is AU$334
includes taxes & fees
23 Sept - 24 Sept
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

Spacious 4-bedroom house with private access to river in Willow River State Park

10.0 out of 10, Exceptional, (5)
"We stayed here based on the terrific location to Willow State Park. The property is gorgeous and you have so many areas to hike and explore including down to a really great stream. The owners were very attentive and they communicated well. Highly recommend this property!"
Spacious 4-bedroom house with private access to river in Willow River State Park

Beautiful Farmhouse Style Country Home with Indoor Pool!

10.0 out of 10, Exceptional, (51)
"It was a wonderful place to stay for the weekend. So much space, activities and accommodations! We would certainly book this place again! "
Beautiful Farmhouse Style Country Home with Indoor Pool!

Lumberjack Inn 2300 sq.ft in DT with a rooftop

9.8 out of 10, Exceptional, (34)
"Great property! Enough space for larger group. "
Lumberjack Inn 2300 sq.ft in DT with a rooftop

Dogs O.K Historic River Home: 6 Beds, 4 Bedrooms, 10 People,

10.0 out of 10, Exceptional, (2)
"The location and property are perfect for a women's trip of hiking, shopping cute shops, wineries, and hanging out. Would stay again!"
Dogs O.K Historic River Home: 6 Beds, 4 Bedrooms, 10 People,

Modern Lake Home!

8.8 out of 10, Excellent, (19)
"Comfortable with great location. Would definitely stay here again. "
The price is AU$844
includes taxes & fees
28 Sept - 29 Sept
Modern Lake Home!

Great Getaway Enjoy Lake Living ~ 20 minutes from St Paul and Wisconsin

9.2 out of 10, Wonderful, (114)
"Very charming and spacious plus an easy walk to the beach. Would definitely do it again!"
Great Getaway Enjoy Lake Living ~ 20 minutes from St Paul and Wisconsin

Cozy 5-Star Guesthouse on Bald Eagle Lake - Serene and Peaceful.

10.0 out of 10, Exceptional, (6)
"Very clean and bright. Would have liked better lake access though"
The price is AU$372
includes taxes & fees
23 Sept - 24 Sept
Cozy 5-Star Guesthouse on Bald Eagle Lake - Serene and Peaceful.

Charming and spacious 5 bedroom, 3 bath,19 guest home on peaceful keewahtin lake

9.8 out of 10, Exceptional, (41)
"Our family loved our stay at the house. We had great weather and were able to use the pontoon boat, kayaks, paddle boats, and canoe on the lake. Kids loved fishing off the dock and catching bluegill too! "
Charming and spacious 5 bedroom, 3 bath,19 guest home on peaceful keewahtin lake

St. Croix Riverview Home...Walking Distance to Downtown Stillwater

9.8 out of 10, Exceptional, (141)
"This property was pleasingly charming and serene, it truly was as beautiful as on the pictures. Excellent host wonderful community. We were truly happy over our stay."
St. Croix Riverview Home...Walking Distance to Downtown Stillwater
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Osceola Hotel Reviews

Find out more about Osceola

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$143 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?

Sleepy Deer Chalet! Spacious, Well-Appointed home on Beautiful Lake Wapogasset!: This holiday home rental outside of Osceola is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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.