A waterfall cascading over a rocky cliff surrounded by lush greenery.

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, (52 reviews)
"Would absolutely stay here again! Lovely location, clean, communicative host, and they shoveled right when it snowed which was especially helpful when I had a 5am clinical rotation!"
United States
Mallorey K.
The price is NZ$296
includes taxes & fees
29 July - 30 July
Cozy Mother-in-Law Apartment

Historic 1880s Home

Historic 1880s Home
Osceola
10.0 out of 10, Exceptional, (79 reviews)
"Great spot to stay for the weekend. Close proximity to downtown. "
United States
Connie S.
The price is NZ$511
includes taxes & fees
28 July - 29 July
Historic 1880s Home

Apple River Retreat home in Amery

Apple River Retreat home in Amery
Amery
10.0 out of 10, Exceptional, (5 reviews)
"Host was very helpful everythig went perfect we had a great time "
United States
Rusty S.
The price is NZ$424
includes taxes & fees
27 July - 28 July
Apple River Retreat home in Amery

Balsam Lake Sunset Cabin with WiFi & Sauna!

Balsam Lake Sunset Cabin with WiFi & Sauna!
Balsam Lake
9.6 out of 10, Exceptional, (47 reviews)
"I had my out of town family stay here and it was just perfect. It's a great location on the lake, easy to get to both by boat and land."
United States
Kris M.
The price is NZ$1,919
includes taxes & fees
9 Aug - 10 Aug
Balsam Lake Sunset Cabin with WiFi & Sauna!

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

Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
Balsam Lake Village
9.0 out of 10, Wonderful, (42 reviews)
"Very clear communication, comfortable beds and all the amenities you need for a night stay!"
United States
Farrah S.
The price is NZ$430
includes taxes & fees
3 Aug - 4 Aug
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

Peaceful 3-bedroom cabin in charming Amery

Peaceful 3-bedroom cabin in charming Amery
Amery
10.0 out of 10, Exceptional, (2 reviews)
"What a beautiful getaway… Charming, amazing property , very relaxing, just lovely!"
United States
Chris D.
The price is NZ$716
includes taxes & fees
29 July - 30 July
Peaceful 3-bedroom cabin in charming Amery

Brand-New House on 130 Acre Farm

Brand-New House on 130 Acre Farm
Wisconsin
10.0 out of 10, Exceptional, (14 reviews)
"Excellent property, friendly host, and great location!"
United States
Jeff P.
The price is NZ$729
includes taxes & fees
27 July - 28 July
Brand-New House on 130 Acre Farm

Classic Home

Classic Home
Centuria
8.2 out of 10, Very good, (38 reviews)
"Nice clean house that fit our needs perfectly. Were on girls weekend and this was great place to stay and then travel around the wider area trying different routes and restaurants. Got great suggestions from the host! "
United States
Melissa
The price is NZ$390
includes taxes & fees
27 July - 28 July
Classic Home

Lake Home property

Lake Home property
Luck
9.2 out of 10, Wonderful, (15 reviews)
"Very nice cozy cabin and such a great, accommodating host! "
United States
Jesse S.
The price is NZ$557
includes taxes & fees
29 July - 30 July
Lake Home property

Lovers Lookout 2 at Big Rock Creek

Lovers Lookout 2 at Big Rock Creek
Saint Croix Falls
10.0 out of 10, Exceptional, (1 review)
"We enjoyed everything about our stay! Just wish we had more time to enjoy the amenities of the property. "
United States
Kim J.
The price is NZ$267
includes taxes & fees
28 July - 29 July
Lovers Lookout 2 at Big Rock Creek

Lovers Lookout 1: Where Rustic Meets Luxury at Big Rock Creek

Lovers Lookout 1: Where Rustic Meets Luxury at Big Rock Creek
Saint Croix Falls
10.0 out of 10, Exceptional, (1 review)
"Everything was clean and nice when we arrived. Check in was easy by text. We were greatedby the owners not long after check in and they delivered us firewood that we purchased. Was an amazing stay and we hope to come back every year !"
United States
Jenny E.
The price is NZ$325
includes taxes & fees
27 July - 28 July
Lovers Lookout 1: Where Rustic Meets Luxury at Big Rock Creek

Romantic Quaint Bell Tent Perfect for a Secluded Couple Escape in Saint Croix Falls, Wisconsin

Romantic Quaint Bell Tent Perfect for a Secluded Couple Escape in Saint Croix Falls, Wisconsin
Saint Croix Falls
The price is NZ$346
includes taxes & fees
27 July - 28 July
Romantic Quaint Bell Tent Perfect for a Secluded Couple Escape in Saint Croix Falls, Wisconsin

The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge

The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
Saint Croix Falls
The price is NZ$305
includes taxes & fees
27 July - 28 July
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge

Gorgeous A-Frame with Panoramic Views, Nestled Atop White Oak Ridge, Wisconsin

Gorgeous A-Frame with Panoramic Views, Nestled Atop White Oak Ridge, Wisconsin
Saint Croix Falls
The price is NZ$367
includes taxes & fees
24 Aug - 25 Aug
Gorgeous A-Frame with Panoramic Views, Nestled Atop White Oak Ridge, Wisconsin

Escape to The Clubhouse, St. Croix Falls city, Wisconsin

Escape to The Clubhouse, St. Croix Falls city, Wisconsin
Saint Croix Falls
The price is NZ$1,581
includes taxes & fees
23 Aug - 24 Aug
Escape to The Clubhouse, St. Croix Falls city, Wisconsin

Escape to The Clubhouse at Big Rock Creek – Your All-Season Adventure Awaits!

Escape to The Clubhouse at Big Rock Creek – Your All-Season Adventure Awaits!
St. Croix
9.6 out of 10, Exceptional, (26 reviews)
"Great for families to play and visit , felt very safe here !"
United States
Karen P.
The price is NZ$1,468
includes taxes & fees
23 Aug - 24 Aug
Escape to The Clubhouse at Big Rock Creek – Your All-Season Adventure Awaits!

Wannigan Point Cabin #4

Wannigan Point Cabin #4
Taylors Falls
10.0 out of 10, Exceptional, (2 reviews)
"Everything was as expected- very clean and well maintained. "
United States
Breanne B.
The price is NZ$397
includes taxes & fees
27 July - 28 July
Wannigan Point Cabin #4

Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm

Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
Taylors Falls
9.8 out of 10, Exceptional, (12 reviews)
"Very conveniently located to downtown Taylors Falls and Interstate Park so we could walk everywhere!"
United States
Allison G.
The price is NZ$334
includes taxes & fees
16 Aug - 17 Aug
Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm

Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (42 reviews)
"Cute place. Everything is very comfy including the beds. Great location. The host was very responsive throughout the booking and checking in process. "
United States
Michelle B.
The price is NZ$719
includes taxes & fees
9 Aug - 10 Aug
Scandinavian Retreat

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
10.0 out of 10, Exceptional, (13 reviews)
"Very clean and exactly as described, would stay again! "
United States
Thomas R.
The price is NZ$445
includes taxes & fees
2 Aug - 3 Aug
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC
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 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$166 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?

MINNeSTAY* St. Croix Valley Inn: This highly rated holiday home rental in Osceola is located on the waterfront, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 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 7 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.