Photo by rinchindorj

Osceola Holiday Rentals

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

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Osceola

Historic 1880s Home
10.0 out of 10, Exceptional, (67)
"The Property was all and more as it was described on VRBO! Very clean, spacious and comfortable for a friend's weekend. Would highly recommend staying here!!"
United States
Debbie C.
The price is NZ$401
includes taxes & fees
22 Oct - 23 Oct
Historic 1880s Home
Hudson Inn & Suites
3.0 star property
8.2 out of 10, Very good, (797)
"The property was perfect for our short stay."
United States
Deb
The price is NZ$143
includes taxes & fees
30 Oct - 31 Oct
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."
United States
Margie O.
Gathering families, friends, & coworkers
Romantic getaway! With gorgeous views from the Hot Tub!
9.4 out of 10, Exceptional, (99)
"Very peaceful and relaxing basement apartment. We were very comfortable for our 6 night stay. "
United States
Laura B.
The price is NZ$459
includes taxes & fees
23 Oct - 24 Oct
Romantic getaway! With gorgeous views from the Hot Tub!
Get away from it all and relax on the lake!
9.8 out of 10, Exceptional, (178)
"We all had a great time - it was a great location to relax!"
United States
Taylor T.
Get away from it all and relax on the lake!
All seasons cabin getaway
10.0 out of 10, Exceptional, (52)
"Amazing cabin and host! Would love to stay again!"
United States
Malinda K.
All seasons cabin getaway
Cozy 5-Star Guesthouse on Bald Eagle Lake - Serene and Peaceful.
9.8 out of 10, Exceptional, (8)
"The guest house was clean, bed was comfortable, overall a good experience"
United States
Peter W.
The price is NZ$424
includes taxes & fees
1 Nov - 2 Nov
Cozy 5-Star Guesthouse on Bald Eagle Lake - Serene and Peaceful.
Historic Swedish Cottage on Quiet Lindstrom Lake
9.4 out of 10, Exceptional, (227)
"beautiful property and great stay for 4 families with kids. Very friendly and helpful host!"
United States
Anna K.
The price is NZ$1,282
includes taxes & fees
25 Oct - 26 Oct
Historic Swedish Cottage on Quiet Lindstrom Lake
Beautiful Farmhouse Style Country Home with Indoor Pool!
10.0 out of 10, Exceptional, (55)
"It was a wonderful place to stay for the weekend. So much space, activities and accommodations! We would certainly book this place again! "
United States
Kailee L.
Beautiful Farmhouse Style Country Home with Indoor Pool!
Lumberjack Inn 2300 sq.ft in DT with a rooftop
9.8 out of 10, Exceptional, (39)
"Great patio"
United States
Greg H.
Lumberjack Inn 2300 sq.ft in DT with a rooftop
Private Suite in historic Stillwater North Hill
10.0 out of 10, Exceptional, (28)
"Highly recommend staying here"
United States
Sally E.
The price is NZ$417
includes taxes & fees
2 Nov - 3 Nov
Private Suite in historic Stillwater North Hill
Great Getaway Enjoy Lake Living ~ 20 minutes from St Paul and Wisconsin
9.2 out of 10, Wonderful, (118)
"Very friendly staff"
United States
Jane
Great Getaway Enjoy Lake Living ~ 20 minutes from St Paul and Wisconsin
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!"
United States
Geoff P.
The price is NZ$378
includes taxes & fees
27 Oct - 28 Oct
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
St. Croix Riverview Home...Walking Distance to Downtown Stillwater
9.8 out of 10, Exceptional, (146)
"We stayed a week in this beautiful home, with our children and grandchildren. It had everything we needed to make this a true vacation. The kitchen and bathrooms were better equipped than my own, and my grandkids (9 and 11) said the beds were the most comfortable they had ever slept in. "
United States
Michele S.
St. Croix Riverview Home...Walking Distance to Downtown Stillwater
Downtown Stilwater, Riverview Condo
10.0 out of 10, Exceptional, (72)
"Property was beautiful, very clean, organized, super convenient for a wedding weekend. You are right on Main Street with access to shopping, dining, and great walking along the river. The condo had a lot of space and areas to use. The views on top were really nice, a great way to spend time outside. We really enjoyed our stay. The only downside was some louder people at night on the street one evening."
United States
Linette
The price is NZ$1,577
includes taxes & fees
2 Nov - 3 Nov
Downtown Stilwater, Riverview Condo
Historic Stillwater Home close to downtown
10.0 out of 10, Exceptional, (54)
"Beautiful property with great touches throughout! Very welcoming and comfortable for our stay! Would definitely stay here again the next time I am visiting Stillwater!"
United States
Michelle B.
The price is NZ$587
includes taxes & fees
2 Nov - 3 Nov
Historic Stillwater Home close to downtown
Luxe Lakefront Estate near Minneapolis, Hot Tub, Sauna, Kayaks, Sleeps up to 20
10.0 out of 10, Exceptional, (5)
"Had a great week here with family. Loved the lake access and space in the house. Also, easy drive to activities in Minneapolis. Location was private and quiet. Great communication with our reservation, too. Thank you!"
United States
Kate L.
Luxe Lakefront Estate near Minneapolis, Hot Tub, Sauna, Kayaks, Sleeps up to 20
Spacious 4-bedroom house with private access to river in Willow River State Park
10.0 out of 10, Exceptional, (9)
"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!"
United States
cory b.
Spacious 4-bedroom house with private access to river in Willow River State Park
Historic James Mulvey Carriage house (Whole house)
9.8 out of 10, Exceptional, (32)
"Great place. Perfect for a fun get together. Has an amazing pool and hot tub. Also close to shopping and music by the water!"
United States
Laurie P.
The price is NZ$1,434
includes taxes & fees
2 Nov - 3 Nov
Historic James Mulvey Carriage house (Whole house)
Log Cabin, Lake Retreat
9.8 out of 10, Exceptional, (85)
"It was a perfect cabin and location for a long weekend getaway! Beautiful view of the lake and plenty of space for a group. "
United States
Randi K.
Log Cabin, Lake Retreat
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

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$143 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?

Historic Swedish Cottage on Quiet Lindstrom Lake: This holiday home rental outside of Osceola is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a private 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.