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

Osceola Holiday Rentals

  • 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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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 NZ$219
includes taxes & fees
27 Oct - 28 Oct
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
9.8 out of 10, Exceptional, (87 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$369
includes taxes & fees
1 Nov - 2 Nov
Historic 1880s Home
A modern kitchen with black cabinets, a white countertop, and a wooden floor.

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

Cambrian & Co. Loft Cozy, Charming, Downtown Ease
Taylors Falls
10.0 out of 10, Exceptional, (29 reviews)
"Good place to stay."
United States
Douglas J.
The price is NZ$349
includes taxes & fees
10 Nov - 11 Nov
Cambrian & Co. Loft Cozy, Charming, Downtown Ease
A cozy cabin interior with a wooden exterior, a green door, a window with a grid pattern, and a rustic wooden wall.

4. 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 NZ$387
includes taxes & fees
15 Nov - 16 Nov
Wannigan Point Cabin #1
A modern living room with a spiral staircase, a sofa set, a coffee table, and a chandelier.

5. Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (46 reviews)
"Thanks for a lovely stay!"
United States
Megan J.
The price is NZ$651
includes taxes & fees
2 Nov - 3 Nov
Scandinavian Retreat
A hotel room with two beds, green walls, and framed pictures of landscapes.

6. Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.4 out of 10, Very good, (966 reviews)
"Softest bed sheets I’ve had in a hotel!"
United States
Rhonda
The price is NZ$155
includes taxes & fees
27 Oct - 28 Oct
Hudson Inn & Suites
A wooden deck with outdoor seating, overlooking a body of water.

7. Nordic Harbor | Room 5 | Cedar Shadows

Nordic Harbor | Room 5 | Cedar Shadows
Center City
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay. Nordic Harbor is a very charming, clean and comfortable boutique hotel! We really enjoyed the patio out back of our room and the rooftop bar overlooking the lake with live music out front of the hotel. We will be back and bring our boat next time!"
United States
Erica F.
The price is NZ$539
includes taxes & fees
27 Oct - 28 Oct
Nordic Harbor | Room 5 | Cedar Shadows
A two-story house with a wooden deck, large windows, and a covered porch area.

8. 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, (12 reviews)
"We loved our stay and only wished we could have stayed longer. Everything in the listing is accurate. Beautiful home."
United States
Angie T.
The price is NZ$697
includes taxes & fees
1 Nov - 2 Nov
Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.
A kitchen with a wooden island, bar stools, a fireplace, and a television.

9. 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$349
includes taxes & fees
1 Nov - 2 Nov
Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
A modern kitchen with a large island, stainless steel appliances, and bar stools.

10. Cozy 3-bedroom cabin on Cedar Lake

Cozy 3-bedroom cabin on Cedar Lake
Star Prairie
9.8 out of 10, Exceptional, (6 reviews)
"We stayed in this home with 6 people. We all fit very comfortably. The kitchen was well stocked. We stayed in the fall but the outdoor seating and dock looked perfect for summer time. Very peaceful! We would stay again!"
United States
Ella
The price is NZ$839
includes taxes & fees
27 Oct - 28 Oct
Cozy 3-bedroom cabin on Cedar Lake
A wooden deck with a view of a lake, outdoor seating, and a building with windows.

11. Nordic Harbor | Room 3 | Arctic Pine - Suite

Nordic Harbor | Room 3 | Arctic Pine - Suite
Center City
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful place and will be staying there again. "
United States
SUZANNE M.
The price is NZ$770
includes taxes & fees
27 Oct - 28 Oct
Nordic Harbor | Room 3 | Arctic Pine - Suite
A kitchen with wooden cabinets, a granite countertop, a window with a faucet, and a black doormat.

12. Classic Home

Classic Home
Centuria
8.2 out of 10, Very good, (43 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$394
includes taxes & fees
5 Nov - 6 Nov
Classic Home
A bedroom with a wooden ceiling, large windows with curtains, a bed with white bedding, and a blanket.

13. Private riverfront cabin with wooded hiking trails

Private riverfront cabin with wooded hiking trails
Amery
9.8 out of 10, Exceptional, (8 reviews)
"What a beautiful getaway… Charming, amazing property , very relaxing, just lovely!"
United States
Chris D.
The price is NZ$648
includes taxes & fees
27 Oct - 28 Oct
Private riverfront cabin with wooded hiking trails
A bedroom with a wooden ceiling, a bed with a white comforter and patterned pillows, a bedside table with a lamp, and a small table with a potted plant.

14. Nordic Harbor | Room 1 | Acorn Oak

Nordic Harbor | Room 1 | Acorn Oak
Center City
10.0 out of 10, Exceptional, (3 reviews)
"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 NZ$539
includes taxes & fees
27 Oct - 28 Oct
Nordic Harbor | Room 1 | Acorn Oak
Relax on Our Porch Swing

15. Historic Swedish Cottage on Quiet Lindstrom Lake

Historic Swedish Cottage on Quiet Lindstrom Lake
Lindstrom
9.4 out of 10, Exceptional, (254 reviews)
"Second time staying at this property with a group and it was excellent once again!"
United States
Leah O.
The price is NZ$1,305
includes taxes & fees
29 Oct - 30 Oct
Historic Swedish Cottage on Quiet Lindstrom Lake
A two-story wooden house with a porch, a stone birdbath, and a brick fire pit.

16. Lake Home property

Lake Home property
Luck
9.2 out of 10, Wonderful, (18 reviews)
"Overall it was a great experience and great location! Host was super communicative. Very clean and good space for our group of 6"
United States
Joseph F.
The price is NZ$459
includes taxes & fees
27 Oct - 28 Oct
Lake Home property
A modern room with a large sliding glass door leading to an outdoor deck with a view of a lake. Inside, there is a bathroom with a toilet and sink, and a bed with a dark blue cover.

17. Nordic Harbor | Room 2 | Tranquil Maple

Nordic Harbor | Room 2 | Tranquil Maple
Center City
8.8 out of 10, Excellent, (3 reviews)
"Absolutely adorable, relaxing and everything’s done with excellence. The room was probably the best I’ve ever stayed in (big statement, I know). So comfortable, beautiful. Loved the rooftop bar. Even on a freezing night it was comfortable with their luxury blankets provided for free. I will definitely be coming back. "
United States
Nicole
The price is NZ$583
includes taxes & fees
27 Oct - 28 Oct
Nordic Harbor | Room 2 | Tranquil Maple
A compact kitchen with a microwave, a sink, and a small countertop.

18. Nordic Harbor | Room 4 | Nordic Spruce

Nordic Harbor | Room 4 | Nordic Spruce
Center City
The price is NZ$539
includes taxes & fees
27 Oct - 28 Oct
Nordic Harbor | Room 4 | Nordic Spruce
A kitchen with wooden cabinets, a white refrigerator, a welcome sign, and a wicker basket.

19. 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, (45 reviews)
"Clean, but rather small for 5 people. Would probably come again"
United States
Chuck B.
The price is NZ$389
includes taxes & fees
8 Nov - 9 Nov
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
A room with a large window overlooking a lake and trees, a round table, and a patterned chair.

20. Apple River Retreat home in Amery

Apple River Retreat home in Amery
Amery
10.0 out of 10, Exceptional, (8 reviews)
"Great last minute find for weekend!"
United States
Dan W.
The price is NZ$402
includes taxes & fees
1 Nov - 2 Nov
Apple River Retreat home in Amery
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

Comfort Inn & Suites St. Paul Northeast

Comfort Inn & Suites St. Paul Northeast

8/10 Good
"Overall it was a nice hotel. breakfast options were just okay. Beds are very firm and not my favorite. Pool was Nice- cold water, water slide only open select hours on Friday, Saturday, Sunday only"
Miranda 4-night trip
Posted 1 hour ago
Comfort Inn & Suites St. Paul Northeast

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$155 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.