Holiday Rentals in Osceola

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Osceola holiday rentals

A kitchen with wooden cabinets, a window, a sink, and various kitchen utensils.

1. 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 €183
includes taxes & fees
9 Nov - 10 Nov
Historic 1880s Home
A two-story house with a front porch, a garage, and a well-maintained lawn.

2. 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 €106
includes taxes & fees
17 Nov - 18 Nov
Cozy Mother-in-Law Apartment
A spacious living room with a fireplace, a large window, and a high ceiling.

3. Historic Beauty w Modern Updates Near Taylor's Falls

Historic Beauty w Modern Updates Near Taylor's Falls
Osceola
9.8 out of 10, Exceptional, (43 reviews)
"Great house! We had a wonderful visit."
United States
Kimberly R.
The price is €284
includes taxes & fees
9 Nov - 10 Nov
Historic Beauty w Modern Updates Near Taylor's Falls
A kitchen with a wooden island, bar stools, a fireplace, and a television.

4. 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 €174
includes taxes & fees
22 Nov - 23 Nov
Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
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)
"Quiet, comfortable, clean, beautifully decorated."
United States
Jeanne M.
The price is €322
includes taxes & fees
9 Nov - 10 Nov
Scandinavian Retreat
A modern kitchen with a large island, stainless steel appliances, and bar stools.

6. 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 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 €419
includes taxes & fees
9 Nov - 10 Nov
Cozy 3-bedroom cabin on Cedar Lake
A wooden deck with a view of a lake, outdoor seating, and a building with windows.

7. 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 €385
includes taxes & fees
16 Nov - 17 Nov
Nordic Harbor | Room 3 | Arctic Pine - Suite
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.

8. 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 €267
includes taxes & fees
9 Nov - 10 Nov
Nordic Harbor | Room 1 | Acorn Oak
A hotel room with two beds, green walls, and framed pictures of landscapes.

9. Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.4 out of 10, Very good, (975 reviews)
"Clean place, and quiet even though it was full. I recommend a stay here for the price"
United States
Steve
The price is €82
includes taxes & fees
25 Nov - 26 Nov
Hudson Inn & Suites
A rustic cabin interior with a stone fireplace, wooden ceiling beams, and a dining area with a table set for four.

10. Where Comfort Meets Adventure — In Every Season!

Where Comfort Meets Adventure — In Every Season!
Saint Croix Falls
9.8 out of 10, Exceptional, (42 reviews)
"We enjoyed our stay so much! There is a lot to do around the area and our cabin was cozy & relaxing. Thank you!"
United States
Pwggy D.
The price is €372
includes taxes & fees
17 Nov - 18 Nov
Where Comfort Meets Adventure — In Every Season!
Relax on Our Porch Swing

11. Historic Swedish Cottage on Quiet Lindstrom Lake

Historic Swedish Cottage on Quiet Lindstrom Lake
Lindstrom
9.4 out of 10, Exceptional, (257 reviews)
"Second time staying at this property with a group and it was excellent once again!"
United States
Leah O.
The price is €688
includes taxes & fees
16 Nov - 17 Nov
Historic Swedish Cottage on Quiet Lindstrom Lake
A barn with a sloped roof, multiple chimneys, and a large door.

12. Elroy's @ Big Rock Creek: Where Adventure Meets Comfort in the St. Croix Valley

Elroy's @ Big Rock Creek: Where Adventure Meets Comfort in the St. Croix Valley
Saint Croix Falls
9.6 out of 10, Exceptional, (4 reviews)
"We had a wonderful time exploring the property. Cant wait to come back with the entire family."
United States
Holly R.
Elroy's @ Big Rock Creek: Where Adventure Meets Comfort in the St. Croix Valley
Exterior

13. Lakefront Cottage Fully Equipped with Excellent Location in Saint Croix Falls, Wisconsin

Lakefront Cottage Fully Equipped with Excellent Location in Saint Croix Falls, Wisconsin
Saint Croix Falls
The price is €1,032
includes taxes & fees
24 Nov - 25 Nov
Lakefront Cottage Fully Equipped with Excellent Location in Saint Croix Falls, Wisconsin
A cozy cabin interior with a wooden exterior, a green door, a window with a grid pattern, and a rustic wooden wall.

14. 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 €193
includes taxes & fees
22 Nov - 23 Nov
Wannigan Point Cabin #1
A modern kitchen with black cabinets, a white countertop, and a wooden floor.

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

Cambrian & Co. Loft Cozy, Charming, Downtown Ease
Taylors Falls
10.0 out of 10, Exceptional, (29 reviews)
"Very nice property, we will be staying here again."
United States
Brian G.
The price is €174
includes taxes & fees
22 Nov - 23 Nov
Cambrian & Co. Loft Cozy, Charming, Downtown Ease
A bedroom with a wooden ceiling, large windows with curtains, a bed with white bedding, and a blanket.

16. Private riverfront cabin with wooded hiking trails

Private riverfront cabin with wooded hiking trails
Amery
9.8 out of 10, Exceptional, (9 reviews)
"What a beautiful getaway… Charming, amazing property , very relaxing, just lovely!"
United States
Chris D.
The price is €297
includes taxes & fees
10 Nov - 11 Nov
Private riverfront cabin with wooded hiking trails
A kitchen with wooden cabinets, a white refrigerator, a welcome sign, and a wicker basket.

17. 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, (46 reviews)
"Clean, but rather small for 5 people. Would probably come again"
United States
Chuck B.
The price is €188
includes taxes & fees
9 Nov - 10 Nov
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
A covered outdoor patio with a table, chairs, and a bench.

18. Nordic Harbor | Room 6 | Silver Birch - Suite

Nordic Harbor | Room 6 | Silver Birch - Suite
Center City
10.0 out of 10, Exceptional, (2 reviews)
"Do not hesitate to book at Nordic Harbor. The rooms are stellar and the location is convenient. Steps away from the room is the Nordic Harbor market and roof top bar. The onsite pontoon rental is a blast, and the lake is beautiful. If you're looking for a quick getaway from the cities, this is it!"
United States
Paul F.
The price is €385
includes taxes & fees
16 Nov - 17 Nov
Nordic Harbor | Room 6 | Silver Birch - Suite
A two-story wooden house with a porch, a stone birdbath, and a brick fire pit.

19. Lake Home property

Lake Home property
Luck
9.2 out of 10, Wonderful, (19 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 €227
includes taxes & fees
9 Nov - 10 Nov
Lake Home property
A wooden interior with a ceiling fan, a woven rug, and a view through a glass door to another room.

20. 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, (3 reviews)
"Very nice,clean property. The only thing it needs is a little more seating in the living room area. A couch would be very nice. We would definitely stay there again."
United States
Trina P.
The price is €511
includes taxes & fees
5 Dec - 6 Dec
Scenic Apple River Retreat - Spacious 4BR Home - Fishing, Tubing & Kayaking
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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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 €82 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.