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Osceola Holiday Rentals

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Holiday Rentals in Osceola

Cozy Mother-in-Law Apartment

Osceola
10.0 out of 10, Exceptional, (49)
"Easy check-in. Clean & quiet, and just a couple blocks walk to a cute downtown area (with a waterfall!). Hosts provided a very comfortable, homey place. Would love to come back!"
United States
Debbie
The price is AU$189
includes taxes & fees
12 Nov - 13 Nov
Cozy Mother-in-Law Apartment

Historic 1880s Home

Osceola
10.0 out of 10, Exceptional, (68)
"Wonderful accommodation in a pleasant town and neighborhood. Hope to stay here again."
United States
Annette E.
The price is AU$351
includes taxes & fees
11 Nov - 12 Nov
Historic 1880s Home

Romantic getaway! With gorgeous views from the Hot Tub!

Taylors Falls
9.4 out of 10, Exceptional, (101)
"We wanted a quick, relaxing get away for the weekend not far from home. It is abeautifully decorated and comfortable space"
United States
Megan O.
The price is AU$410
includes taxes & fees
11 Nov - 12 Nov
Romantic getaway! With gorgeous views from the Hot Tub!

Private Suite in historic Stillwater North Hill

Stillwater
10.0 out of 10, Exceptional, (29)
"Highly recommend staying here"
United States
Sally E.
The price is AU$364
includes taxes & fees
11 Nov - 12 Nov
Private Suite in historic Stillwater North Hill

Come check out this Cozy 2-bedroom cabin in charming Amery!

Amery
10.0 out of 10, Exceptional, (5)
"Lovely cabin... Clean, well supplied. Great location, peaceful, lots of places to visit, friendly community and amazing hosts."
United States
Susan S.
The price is AU$367
includes taxes & fees
11 Nov - 12 Nov
Come check out this Cozy 2-bedroom cabin in charming Amery!

Private 3bdr cabin on Apple River kayaks, SUPS, and paddle boat. Pet friendly!

Amery
9.8 out of 10, Exceptional, (8)
"We thoroughly enjoyed our stay. The use of the kayaks and SUPs was a highlight for our son and his 10 year old daughter. Our daughter and son-in-law also enjoyed them. The cabin was fantastic and beyond our expectations. We had the use of both units in the cabin. We definitely will stay here again for a family vacation!"
United States
Gary L.
The price is AU$482
includes taxes & fees
11 Nov - 12 Nov
Private 3bdr cabin on Apple River kayaks, SUPS, and paddle boat. Pet friendly!

Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC

Somerset
9.8 out of 10, Exceptional, (9)
"The pictures really dont do this place justice. Terrys place is decorated so perfectly I want to remodel my kitchen. We had all appliances we needed, beds were comfortable, towels were soft, plenty of room to gather and chat. The little amenities the host left were great! Even though it was very hot the ac kept up just fine. The mornings on porch are definitely the best way to start your morning. Communitcation, check in and check out were a breeze. Thank you so much, we look forward to...
United States
Aimee H.
The price is AU$355
includes taxes & fees
11 Nov - 12 Nov
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC

Scandinavian Retreat

Taylors Falls
10.0 out of 10, Exceptional, (33)
"The property was so clean and beautifully decorated. Thoughtful hosts and lovely community. "
United States
Hollie A.
The price is AU$545
includes taxes & fees
11 Nov - 12 Nov
Scandinavian Retreat

Minne-GetAway: Modern Cottage

North Saint Paul
9.6 out of 10, Exceptional, (13)
"Nancy was very responsive, check in easy. Quiet area! House accommodating to our needs. "
United States
Amber P.
The price is AU$402
includes taxes & fees
11 Nov - 12 Nov
Minne-GetAway: Modern Cottage

River road cabin

Saint Croix Falls
8.0 out of 10, Very good, (14)
"Beautiful little cabin. Lots of space in around the house with a nice fire pit ready for cooking. Really like the kitchen area and the ciuch in the living room was very comfortsbek for relaxing after a good day."
United States
peder
The price is AU$320
includes taxes & fees
11 Nov - 12 Nov
River road cabin

Reflections Retreat on Lake Magnor in Clayton, WI with beautiful lake view

Clayton
10.0 out of 10, Exceptional, (4)
"Was great hosted and very nice place."
United States
Jennifer w.
The price is AU$454
includes taxes & fees
12 Nov - 13 Nov
Reflections Retreat on Lake Magnor in Clayton, WI with beautiful lake view

Historic Stillwater Home close to downtown

Stillwater
10.0 out of 10, Exceptional, (57)
"We had a great time on the 4th of July, The home was in an excellent location and was thoughtfully decorated.Thank you for a great stay!"
United States
Ann S.
The price is AU$525
includes taxes & fees
11 Nov - 12 Nov
Historic Stillwater Home close to downtown

Garden setting within walking distance of River, Local Shops, and Restaurants!

Hudson
9.4 out of 10, Exceptional, (16)
"Gorgeous property. The home was pristine. Fabulous in town location near restaurants, shops and the beautiful St. Croix river. "
United States
Michele L.
The price is AU$576
includes taxes & fees
12 Nov - 13 Nov
Garden setting within walking distance of River, Local Shops, and Restaurants!

Lakefront, Hot Tub, Golf, Kayaks, ATV, Snowmobile Trails, St.Croix Casino

Turtle Lake
10.0 out of 10, Exceptional, (15)
"Really nice and gorgeous house, really clean, has everything you need for the days to stay in. I definitely recommend to everyone. "
United States
Tatyana G.
The price is AU$1,081
includes taxes & fees
11 Nov - 12 Nov
Lakefront, Hot Tub, Golf, Kayaks, ATV, Snowmobile Trails, St.Croix Casino

Home on the Apple River

Amery
10.0 out of 10, Exceptional, (2)
"We definitely found a hidden gem with this one. it was a last minutw booking over thebbusy 4th of July weekend and we stumbled across this location. I think we got really lucky to find such a great place with little notice. the view and location on the river was fantastic through the big windows or the cute play house and play set in the back. Plenty of room for our dogs to play there too.inside there was ample room for 4 adults, we even had guests come for dinner! we felt so comfortable...
United States
Laura K.
The price is AU$349
includes taxes & fees
11 Nov - 12 Nov
Home on the Apple River

Nordic Harbor | Room 1 | Acorn Oak

Center City
10.0 out of 10, Exceptional, (2)
"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$477
includes taxes & fees
11 Nov - 12 Nov
Nordic Harbor | Room 1 | Acorn Oak

Classic Home

Centuria
8.2 out of 10, Very good, (34)
"Was a great house, very clean and great communication with host. Would stay there again!"
United States
Julie S.
The price is AU$339
includes taxes & fees
16 Nov - 17 Nov
Classic Home

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

Hugo
9.8 out of 10, Exceptional, (8)
"Beautiful lake area. "
United States
Jayne O.
The price is AU$380
includes taxes & fees
12 Nov - 13 Nov
Cozy 5-Star Guesthouse on Bald Eagle Lake - Serene and Peaceful.

Lilac Apartment - 5 Minutes to Downtown Stillwater

Stillwater
8.6 out of 10, Excellent, (8)
"Very nice place. Plenty of room for 6 of us. Definitely would recommend! "
United States
Patricia
The price is AU$657
includes taxes & fees
11 Nov - 12 Nov
Lilac Apartment - 5 Minutes to Downtown Stillwater

Spacious light-filled house near Stillwater - The Stone's Throw Riverhouse

Stillwater
9.2 out of 10, Wonderful, (14)
"Hi Jo, THANK YOU for Sharing your Home, with us! It is a GREAT HOUSE and we LOVED Every part of it!! FIVE + STARS! We will be back in a couple of months and will definitely STAY WITH YOU!! THANKS, AGAIN👍‼️"
United States
Bob W.
The price is AU$985
includes taxes & fees
12 Nov - 13 Nov
Spacious light-filled house near Stillwater - The Stone's Throw Riverhouse
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$136 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?

Historic Stillwater Home close to downtown: This holiday home rental outside of Osceola offers a patio, a private garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. 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?

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.