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Osceola Holiday Rentals

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Holiday Rentals in Osceola

Our top choices for Osceola holiday rentals

Hudson Inn & Suites

3.0 star property
8.2 out of 10, Very good, (760)
"This is a great place to stay! It was really clean! And we appreciated how quick the staff checked us in. "
The price is NZ$161
includes taxes & fees
31 Aug - 1 Sept
Hudson Inn & Suites

Gathering families, friends, & coworkers

9.8 out of 10, Exceptional, (36)
"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

Hideaway from the Twin Cities: sharing my home, 5 single rooms, 2 adults 80/rm.

9.6 out of 10, Exceptional, (35)
"We had a great stay!"
Hideaway from the Twin Cities: sharing my home, 5 single rooms, 2 adults 80/rm.

Get away from it all and relax on the lake!

9.8 out of 10, Exceptional, (174)
"We didn’t use hardly any of the amenities, but it was a good place to land at the end of every busy family day. "
Get away from it all and relax on the lake!

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

10.0 out of 10, Exceptional, (24)
"This is our third stay at the property. It is perfect for our family "
Sleepy Deer Chalet! Spacious, Well-Appointed home on Beautiful Lake Wapogasset!

All seasons cabin getaway

10.0 out of 10, Exceptional, (49)
"Was a great stay! We brought a boat and parked it at the dock for the entire stay... worked very well. Property is right there next to the lake and you're walking distance to several places to eat and drink."
All seasons cabin getaway

Romantic getaway! With gorgeous views from the Hot Tub!

9.4 out of 10, Exceptional, (96)
"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 NZ$450
includes taxes & fees
3 Sept - 4 Sept
Romantic getaway! With gorgeous views from the Hot Tub!

Beautiful, clear water lakefront 2-bedroom cabin on Horseshoe Lake pet friendly

10.0 out of 10, Exceptional, (6)
Beautiful, clear water lakefront 2-bedroom cabin on Horseshoe Lake pet friendly

Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options

9.4 out of 10, Exceptional, (44)
"Nice and spacious."
Hideaway From The Twin Cities: Sharing my personal residence, 5 Bedroom options

Lake Home property

10.0 out of 10, Exceptional, (8)
"The Lake Home was perfect for my trip. The home was immaculate with more than enough space and accommodations. The location is private and quiet. Would definitely recommend, exceeds many higher priced locations!"
The price is NZ$484
includes taxes & fees
15 Sept - 16 Sept
Lake Home property

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 NZ$369
includes taxes & fees
3 Sept - 4 Sept
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

Historic Swedish Cottage on Quiet Lindstrom Lake

9.4 out of 10, Exceptional, (220)
"Very homey, open spaces in home for a group to be together. Easy walk to interesting shops. Felt safe to take walks in. Beautiful lake side location."
The price is NZ$1,140
includes taxes & fees
2 Sept - 3 Sept
Historic Swedish Cottage on Quiet Lindstrom Lake

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,

Lucky View Lodge Log Cabin on Big Butternut Lake Luck, WI 3 acre 300ft lakeshore

10.0 out of 10, Exceptional, (27)
"Clean and quiet "
Lucky View Lodge Log Cabin on Big Butternut Lake Luck, WI 3 acre 300ft lakeshore

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

10.0 out of 10, Exceptional, (6)
The price is NZ$450
includes taxes & fees
8 Sept - 9 Sept
Cozy 5-Star Guesthouse on Bald Eagle Lake - Serene and Peaceful.

Lumberjack Inn 2300 sq.ft in DT with a rooftop

9.6 out of 10, Exceptional, (32)
"Property was clean, welcoming, and well situated in downtown Stillwater. Rooftop seating area was awesome. Very responsive hosts. Will stay again!"
Lumberjack Inn 2300 sq.ft in DT with a rooftop

Private Suite in historic Stillwater North Hill

10.0 out of 10, Exceptional, (23)
"Highly recommend staying here"
The price is NZ$424
includes taxes & fees
4 Sept - 5 Sept
Private Suite in historic Stillwater North Hill

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)
"We had a great time enjoying the house, including the pool, tennis courts, and fire ring!"
Beautiful Farmhouse Style Country Home with Indoor Pool!

Historic James Mulvey Carriage house (Whole house)

9.8 out of 10, Exceptional, (29)
"Very nice accommodations within walking distance to town. Enjoyed our stay!"
The price is NZ$1,406
includes taxes & fees
2 Sept - 3 Sept
Historic James Mulvey Carriage house (Whole house)
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

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$161 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?

Hideaway from the Twin Cities: sharing my home, 5 single rooms, 2 adults 80/rm.: This holiday home rental outside of Osceola is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. 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.

How many holiday rentals are there in Osceola?

Choose from 4 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.