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

Holiday Rentals in Osceola

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Osceola holiday rentals

A two-story house with a front porch, a garage, and a well-maintained lawn.

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 €118
includes taxes & fees
28 Sept - 29 Sept
Cozy Mother-in-Law Apartment
A kitchen with wooden cabinets, a window, a sink, and various kitchen utensils.

2. Historic 1880s Home

Historic 1880s Home
Osceola
10.0 out of 10, Exceptional, (84 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 €218
includes taxes & fees
1 Oct - 2 Oct
Historic 1880s Home
A kitchen with a wooden island, bar stools, a fireplace, and a television.

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 €181
includes taxes & fees
27 Sept - 28 Sept
Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
A kitchen with wooden cabinets, a white refrigerator, a microwave, a stove, and a sink.

4. Wannigan Point Cabin #2

Wannigan Point Cabin #2
Taylors Falls
10.0 out of 10, Exceptional, (5 reviews)
"I had a great stay at Wannigan Point. The cabin was exactly what I needed, very quiet despite being quite close to town. Plenty of shops, restaurants, and nature nearby."
United States
Elijah T.
The price is €203
includes taxes & fees
28 Sept - 29 Sept
Wannigan Point Cabin #2
A campsite with a tent, a grill, and outdoor seating.

5. 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 €139
includes taxes & fees
27 Sept - 28 Sept
Lovers Lookout 2 at Big Rock Creek
A modern living room with a spiral staircase, a sofa set, a coffee table, and a chandelier.

6. 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 €355
includes taxes & fees
5 Oct - 6 Oct
Scandinavian Retreat
A large barn-like building with a sloped roof and multiple chimneys, illuminated by warm lights.

7. 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 €128
includes taxes & fees
29 Sept - 30 Sept
Lovers Lookout 3 at Big Rock Creek
A wooden cabin with a triangular roof, a central door, and a small window.

8. 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 €160
includes taxes & fees
28 Sept - 29 Sept
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
A dock with two boats, a wooden deck, and a small outdoor seating area.

9. 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 €277
includes taxes & fees
27 Sept - 28 Sept
Nordic Harbor | Room 5 | Cedar Shadows
A modern kitchen with a large island, wooden chairs, and a fireplace.

10. 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 €405
includes taxes & fees
29 Sept - 30 Sept
Cozy 3-bedroom cabin on Cedar Lake
A kitchen with wooden cabinets, a granite countertop, a window with a faucet, and a black doormat.

11. Classic Home

Classic Home
Centuria
8.2 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 €199
includes taxes & fees
29 Sept - 30 Sept
Classic Home
A two-story house with a wooden deck, large windows, and a covered porch area.

12. 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, (9 reviews)
The price is €415
includes taxes & fees
29 Sept - 30 Sept
Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.
A cozy cabin interior with a wooden exterior, a green door, a window with a grid pattern, and a rustic wooden wall.

13. Wannigan Point Cabin #1

Wannigan Point Cabin #1
Taylors Falls
8.0 out of 10, Very good, (3 reviews)
"Nice midsized cabin with all the amenities. Quiet for the most part (trucks on the highway nearby). Communication with Mariah was very clear. We enjoyed our little “retreat”."
United States
Eric O.
The price is €207
includes taxes & fees
29 Sept - 30 Sept
Wannigan Point Cabin #1

14. 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 €178
includes taxes & fees
28 Sept - 29 Sept
Gorgeous A-Frame with Panoramic Views, Nestled Atop White Oak Ridge, Wisconsin
A cozy cabin with a porch, outdoor seating, and a fire pit.

15. Huge tent with AC at Big Rock Creek

Huge tent with AC at Big Rock Creek
Saint Croix Falls
The price is €190
includes taxes & fees
6 Oct - 7 Oct
Huge tent with AC at Big Rock Creek
A room with a large window overlooking a lake and trees, a round table, and a patterned chair.

16. Apple River Retreat home in Amery

Apple River Retreat home in Amery
Amery
10.0 out of 10, Exceptional, (7 reviews)
"Great last minute find for weekend!"
United States
Dan W.
The price is €207
includes taxes & fees
28 Sept - 29 Sept
Apple River Retreat home in Amery
A campsite with a tent, a grill, and outdoor seating.

17. 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 €154
includes taxes & fees
29 Sept - 30 Sept
Lovers Lookout 1: Where Rustic Meets Luxury at Big Rock Creek
A wooden deck with a bench, a hot tub, and a pergola covered with greenery.

18. Private Suite in historic Stillwater North Hill

Private Suite in historic Stillwater North Hill
Stillwater
10.0 out of 10, Exceptional, (47 reviews)
The price is €218
includes taxes & fees
30 Sept - 1 Oct
Private Suite in historic Stillwater North Hill
A wooden porch with a red door, two wall-mounted lights, a star decoration, and a number sign.

19. 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.
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC
A hotel room with two beds, green walls, and framed pictures of landscapes.

20. Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very good, (928 reviews)
"Friendly staff and safe place to stay."
United States
Terry
The price is €84
includes taxes & fees
5 Oct - 6 Oct
Hudson Inn & Suites
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osceola Hotel Reviews

Hotel Crosby

Hotel Crosby

10/10 Excellent
"We came as a spur of the moment get away for our anniversary. The staff were all amazing. We got our key, got to the room and they upgraded us massively to an amazing suite without mentioning it. I had to call down and make sure someone didn’t mess up. The lady said no maam we heard it was your anniversary. Absolutely gorgeous! Not to mention a complimentary bottle of wine and card as well. We will most definitely be coming back."
Aaron 1-night trip
Posted 22 hours ago
Hotel Crosby

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, apart-hotels, 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 €84 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 1880s Home: This highly rated holiday home rental in Osceola is located on a river, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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?

Farmington Bottoms State Natural Area and Saint Croix 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.