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

1. 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$265
includes taxes & fees
28 Sept - 29 Sept
Cozy Mother-in-Law Apartment

2. Historic 1880s Home

Historic 1880s Home
Osceola
10.0 out of 10, Exceptional, (83 reviews)
"Rooms are clean, kitchen is well supplied. If you enjoy staying at historic buildings, this would be a good fit for you."
United States
Kathleen R.
The price is NZ$419
includes taxes & fees
15 Sept - 16 Sept
Historic 1880s Home

3. Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm

Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
Taylors Falls
9.8 out of 10, Exceptional, (13 reviews)
"Great location in the heart of Taylor's Falls and the room was well furnished and very clean. Overall a great stay!"
United States
Jacob P.
The price is NZ$332
includes taxes & fees
14 Sept - 15 Sept
Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm

4. 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$263
includes taxes & fees
21 Sept - 22 Sept
Lovers Lookout 2 at Big Rock Creek

5. 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
10.0 out of 10, Exceptional, (1 review)
"Great experience"
United States
Lori M.
The price is NZ$299
includes taxes & fees
21 Sept - 22 Sept
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge

6. Lovers Lookout 3 at Big Rock Creek

Lovers Lookout 3 at Big Rock Creek
Saint Croix Falls
9.8 out of 10, Exceptional, (6 reviews)
"We had an amazing time. The set up is so cute and it’s very peaceful. Very comfortable beds and extremely clean. Loved it!"
United States
Jessica O.
The price is NZ$263
includes taxes & fees
14 Sept - 15 Sept
Lovers Lookout 3 at Big Rock Creek

7. Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (43 reviews)
"Thanks for a lovely stay!"
United States
Megan J.
The price is NZ$686
includes taxes & fees
16 Sept - 17 Sept
Scandinavian Retreat

8. Cambrian & Co. Loft Cozy, Charming, Downtown Ease

Cambrian & Co. Loft Cozy, Charming, Downtown Ease
Taylors Falls
10.0 out of 10, Exceptional, (26 reviews)
"Good place to stay."
United States
Douglas J.
The price is NZ$332
includes taxes & fees
10 Sept - 11 Sept
Cambrian & Co. Loft Cozy, Charming, Downtown Ease

9. Cozy 3-bedroom cabin on Cedar Lake

Cozy 3-bedroom cabin on Cedar Lake
Star Prairie
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved our stay. What started as a simple family weekend at the lake turned into one of those trips we’ll remember for a long time.Our boys practically lived on the dock. They fished for hours, celebrated every catch like it was a trophy fish, and couldn’t wait to get back out there the next morning. We cooked what they caught, spent our evenings by the water, and genuinely enjoyed just being together without needing an itinerary or much of anything else.There’s something special...
United States
Mike R.
The price is NZ$761
includes taxes & fees
10 Sept - 11 Sept
Cozy 3-bedroom cabin on Cedar Lake

10. Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very good, (914 reviews)
"Friendly staff and safe place to stay."
United States
Terry
The price is NZ$164
includes taxes & fees
20 Sept - 21 Sept
Hudson Inn & Suites

11. Classic Home

Classic Home
Centuria
8.0 out of 10, Very good, (40 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$377
includes taxes & fees
17 Sept - 18 Sept
Classic Home

12. Nordic Harbor | Room 5 | Cedar Shadows

Nordic Harbor | Room 5 | Cedar Shadows
Center City
9.8 out of 10, Exceptional, (10 reviews)
"VRBO makes a quick getaway so seamless. Stayed in town for a family wedding and could not have been happier with the location. Great rooftop bar with craft cocktails and good beer wine selection. Soon to have restaurant. Gift/essential shop below bar. Really nice people and great view."
United States
Karie S.
The price is NZ$519
includes taxes & fees
20 Sept - 21 Sept
Nordic Harbor | Room 5 | Cedar Shadows

13. 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$330
includes taxes & fees
14 Sept - 15 Sept
Gorgeous A-Frame with Panoramic Views, Nestled Atop White Oak Ridge, Wisconsin

14. Riverside Historic Home near Downtown, Wineries, Hiking

Riverside Historic Home near Downtown, Wineries, Hiking
Taylors Falls
10.0 out of 10, Exceptional, (21 reviews)
"The house was adorable. Clean, organized with personal touches everywhere. The host Andrea was amazing. Would recommend."
United States
Abigail T.
The price is NZ$1,027
includes taxes & fees
17 Sept - 18 Sept
Riverside Historic Home near Downtown, Wineries, Hiking

15. Huge tent with AC at Big Rock Creek

Huge tent with AC at Big Rock Creek
Saint Croix Falls
The price is NZ$344
includes taxes & fees
14 Sept - 15 Sept
Huge tent with AC at Big Rock Creek

16. Scenic Apple River Retreat - Spacious 4BR Home - Fishing, Tubing & Kayaking

Scenic Apple River Retreat - Spacious 4BR Home - Fishing, Tubing & Kayaking
Somerset
10.0 out of 10, Exceptional, (1 review)
"Mike was a great host and was FAST at communicating. I need to comment that I only gave 4 stars on cleaning. On special request, the host got the house ready a week early on the condition I agreed that it was not quite ready to his normal standards and we were the first guests ever in his new property. The yard was huge, no next neighbors crowding you. Kitchen has everything. Bathrooms furnished with towels, soaps, shampoo, etc. The river is just behind the house. We had fun wading,...
United States
David
The price is NZ$758
includes taxes & fees
15 Sept - 16 Sept
Scenic Apple River Retreat - Spacious 4BR Home - Fishing, Tubing & Kayaking

17. Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.

Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.
center city
10.0 out of 10, Exceptional, (7 reviews)
The price is NZ$759
includes taxes & fees
13 Sept - 14 Sept
Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.

18. 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, (15 reviews)
"Very clean and exactly as described, would stay again! "
United States
Thomas R.
The price is NZ$402
includes taxes & fees
16 Sept - 17 Sept
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC

19. Geo Dome at Big Rock Creek!

Geo Dome at Big Rock Creek!
Saint Croix Falls
The price is NZ$503
includes taxes & fees
15 Sept - 16 Sept
Geo Dome at Big Rock Creek!

20. Private Suite in historic Stillwater North Hill

Private Suite in historic Stillwater North Hill
Stillwater
10.0 out of 10, Exceptional, (45 reviews)
"This suite was perfect! It was little and cute yet had what was needed. The hosts were very responsive and wonderful. Beautiful well kept property. Would definitely recommend!"
United States
Randy
The price is NZ$435
includes taxes & fees
15 Sept - 16 Sept
Private Suite in historic Stillwater North Hill
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$164 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 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.