Osceola, WI Vacation Homes from ￥24,306

Osceola Vacation Homes
United States of America
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A waterfall cascading over a rocky cliff surrounded by lush greenery.

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Our top choices for Osceola vacation homes

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

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

A hammock chair with a striped cushion and a pillow, suspended by ropes and a wooden beam, attached to a white railing on a porch.

A traditional interior with a wooden floor, a sofa set, a dining table with chairs, a chandelier, and a large wooden door.

1. Historic 1880s Home

Historic 1880s Home

Osceola

10.0 out of 10, Exceptional, (85 reviews)

10/10

Exceptional

(85 reviews)

"Rooms are clean, kitchen is well supplied. If you enjoy staying at historic buildings, this would be a good fit for you."

Kathleen R.

The price is ￥28,192

￥28,192

￥35,156 total

includes taxes & fees

Oct 6 - Oct 7

Historic 1880s Home

A campsite with a tent, a grill, and outdoor seating.

An aerial view of a large property with a main building, a barn, and a river.

An inflatable play structure with slides and a small enclosed area.

A wooden structure over a calm body of water, surrounded by trees and vegetation.

2. 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)

10/10

Exceptional

(1 review)

"We enjoyed everything about our stay! Just wish we had more time to enjoy the amenities of the property. "

Kim J.

The price is ￥12,432

￥12,432

￥24,306 total

includes taxes & fees

Oct 1 - Oct 2

Lovers Lookout 2 at Big Rock Creek

A modern living room with a spiral staircase, a sofa set, a coffee table, and a chandelier.

A dining area with a round table, four black chairs, and a yellow pendant light.

A kitchen with white cabinets, a blue island with stools, and a window with blinds.

A modern living room with a sofa, coffee table, and potted plants.

3. Scandinavian Retreat

Scandinavian Retreat

Taylors Falls

10.0 out of 10, Exceptional, (44 reviews)

10/10

Exceptional

(44 reviews)

"Thanks for a lovely stay!"

Megan J.

The price is ￥28,043

￥28,043

￥61,221 total

includes taxes & fees

Oct 12 - Oct 13

Scandinavian Retreat

A wooden cabin with a triangular roof, a central door, and a small window.

A wooden cabin with a sloped roof, situated by a stream with snow on the ground and surrounding trees.

A cozy attic bedroom with a sloped ceiling, a bed with white linens, a fluffy rug, and a window providing a view of trees.

A triangular wooden cabin with a glass door, surrounded by trees and snow-covered ground.

4. 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)

10/10

Exceptional

(1 review)

"Great experience"

Lori M.

The price is ￥17,153

￥17,153

￥29,618 total

includes taxes & fees

Oct 7 - Oct 8

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.

A modern building with a well-maintained lawn and a tree in the foreground.

A compact kitchen with a wooden ceiling, a built-in sink, and a microwave.

A row of modern, two-story buildings with large windows and a well-maintained lawn.

5. Nordic Harbor | Room 5 | Cedar Shadows

Nordic Harbor | Room 5 | Cedar Shadows

Center City

9.8 out of 10, Exceptional, (10 reviews)

9.8/10

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."

Karie S.

The price is ￥37,769

￥37,769

￥48,901 total

includes taxes & fees

Oct 1 - Oct 2

Nordic Harbor | Room 5 | Cedar Shadows

A two-story house with a wooden deck, large windows, and a covered porch area.

A spacious living area with a large window, a comfortable seating arrangement, and a modern kitchen.

A wooden cabin with a porch, a grill, and a stone pathway leading to the entrance.

A modern kitchen with dark cabinets, stainless steel appliances, a wooden island, and a view of the outdoors.

6. 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, (10 reviews)

10/10

Exceptional

(10 reviews)

"We had a wonderful time staying in this beautiful house. House was very clean, well decorated and had everything we needed.Quiet location but only minutes away from great wineries and restaurants.Highly recommend!"

Karen M.

The price is ￥42,490

￥42,490

￥71,912 total

includes taxes & fees

Oct 1 - Oct 2

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

A kitchen with wooden cabinets, a granite countertop, a window with a faucet, and a black doormat.

A house with a wooden front porch, a white door, and a small garden with green plants and pink flowers.

A room with a sloped ceiling, a bed, a window with curtains, a patterned rug, and a staircase with a metal railing.

A kitchen with wooden cabinets, a granite countertop, a microwave, a coffee maker, and a window providing natural light.

7. Classic Home

Classic Home

Centuria

8.2 out of 10, Very good, (41 reviews)

8.2/10

Very good

(41 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! "

Melissa

The price is ￥19,671

￥19,671

￥35,696 total

includes taxes & fees

Oct 1 - Oct 2

Classic Home

A room with wooden walls, a round table with a white top, wicker chairs, two hanging chairs with cushions, and large windows with greenery outside.

A neatly made bed with a white comforter, a wicker tray with two cups and a plant, and a textured throw blanket.

Two hanging chairs with cushions, a wooden floor, and a large window with a view of trees.

A modern kitchen with a central island, pendant lighting, wooden cabinets, and a dining area with a table and chairs.

8. Riverside Historic Home near Downtown, Wineries, Hiking

Riverside Historic Home near Downtown, Wineries, Hiking

Taylors Falls

10.0 out of 10, Exceptional, (22 reviews)

10/10

Exceptional

(22 reviews)

"Very smooth and easy stay. Home was well thought out and instructions for everything were very well laid out. "

Elite Motorsports

The price is ￥43,277

￥43,277

￥101,915 total

includes taxes & fees

Oct 25 - Oct 26

Riverside Historic Home near Downtown, Wineries, Hiking

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.

A bathroom with a shower, sink, mirror, towel rack, and toilet.

A modern kitchen with wooden paneling, a black door with a number, a microwave, and a sink with a soap dispenser.

A door with a number 1 handle and a keyhole.

9. Nordic Harbor | Room 1 | Acorn Oak

Nordic Harbor | Room 1 | Acorn Oak

Center City

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 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."

Alisha H.

The price is ￥37,769

￥37,769

￥48,727 total

includes taxes & fees

Oct 8 - Oct 9

Nordic Harbor | Room 1 | Acorn Oak

Great Room with Fireplace and Game Table

2nd Floor Sitting Room Doubles as Sleeping Area

Formal Dining Room with Additional Table in Family Room

10. Historic Swedish Cottage on Quiet Lindstrom Lake

Historic Swedish Cottage on Quiet Lindstrom Lake

Lindstrom

9.4 out of 10, Exceptional, (250 reviews)

9.4/10

Exceptional

(250 reviews)

"Second time staying at this property with a group and it was excellent once again!"

Leah O.

The price is ￥66,882

￥66,882

￥119,156 total

includes taxes & fees

Oct 5 - Oct 6

Historic Swedish Cottage on Quiet Lindstrom Lake

A compact kitchen with a microwave, a sink, and a small countertop.

A black door with the number 4, a wooden bench, and a wall-mounted sign.

11. Nordic Harbor | Room 4 | Nordic Spruce

Nordic Harbor | Room 4 | Nordic Spruce

Center City

The price is ￥37,769

￥37,769

￥49,074 total

includes taxes & fees

Oct 11 - Oct 12

Nordic Harbor | Room 4 | Nordic Spruce

A large, historic building with a prominent tower and arched windows, featuring a classic architectural style.

A kitchen with a microwave, coffee maker, and wooden cabinets containing dishes and cookware.

A house with a fire pit in the front yard.

A kitchen with wooden cabinets, a white refrigerator, a welcome sign, and a wicker basket.

12. 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)

9.0/10

Wonderful

(45 reviews)

"Very clear communication, comfortable beds and all the amenities you need for a night stay!"

Farrah S.

The price is ￥20,301

￥20,301

￥36,693 total

includes taxes & fees

Oct 18 - Oct 19

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

A wooden interior with a ceiling fan, a woven rug, and a view through a glass door to another room.

A spacious living room with leather armchairs, a coffee table, and a globe.

A modern kitchen with white cabinetry, a black tiled backsplash, a stainless steel dishwasher, a double oven, and a window with a view of greenery.

A bedroom with a wooden bed, a chair, a small stool, and a wardrobe.

13. 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)

10/10

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."

Trina P.

The price is ￥46,031

￥46,031

￥92,229 total

includes taxes & fees

Oct 4 - Oct 5

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

A living room with a fireplace, two armchairs, a dining area with a table and chairs, and a view through an archway to the outside.

A hallway with a white door, a small window, a white dresser with drawers, a woven basket on a table, and a woven rug on the floor.

A kitchen with dark cabinets, stainless steel appliances, a wooden countertop, and a small rug on the floor.

A dining area with a wooden table, chairs, a chandelier, and a view through an open door.

14. White Bear Lake House 3 blocks from Downtown and Lake!

White Bear Lake House 3 blocks from Downtown and Lake!

White Bear Lake

The price is ￥28,185

￥28,185

￥48,114 total

includes taxes & fees

Oct 1 - Oct 2

White Bear Lake House 3 blocks from Downtown and Lake!

A dock with two boats, a wooden deck, and a sandy area with a small chair and table.

A living room with a wooden floor, a large TV, a wooden cabinet, a small table, and a window with blinds.

A modern living room with a wooden floor, a TV mounted on the wall, a dining table with a basket, a plant, and a trash bin.

A modern living room with a wooden ceiling, a large window, a sofa, a coffee table, and a dining area with chairs and a table.

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

Nordic Harbor | Room 6 | Silver Birch - Suite

Center City

10.0 out of 10, Exceptional, (2 reviews)

10/10

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!"

Paul F.

The price is ￥55,080

￥55,080

￥70,959 total

includes taxes & fees

Oct 8 - Oct 9

Nordic Harbor | Room 6 | Silver Birch - Suite

A dining area with a wooden table, grey upholstered chairs, and a tray with beverages and snacks.

A bed with a yellow quilt, a wooden headboard, and a window with a view of a white fence.

A deck with wicker chairs and a glass table, surrounded by a white railing.

A two-story house with a red exterior, a white garage door, and a gravel driveway.

16. Relaxing Townhouse Escape

Relaxing Townhouse Escape

Hugo

9.2 out of 10, Wonderful, (25 reviews)

9.2/10

Wonderful

(25 reviews)

"Nice clean place. Perfect for what we needed."

Sara C.

The price is ￥35,408

￥35,408

￥57,306 total

includes taxes & fees

Oct 1 - Oct 2

Relaxing Townhouse Escape

A two-story house with a front porch, brick facade, and a garage.

A laundry room with a washing machine, a small window with blinds, a hanging rack, and a shelf with folded clothes.

A modern kitchen with white cabinets, a granite countertop, a built-in microwave, and a stainless steel refrigerator.

A living room with a dark-colored sofa, a recliner, a treadmill, and a large window with curtains.

17. Historic Stillwater Home close to downtown

Historic Stillwater Home close to downtown

Stillwater

10.0 out of 10, Exceptional, (88 reviews)

10/10

Exceptional

(88 reviews)

"Our host was lovely, the property was great, and our stay was one to remember. I can't wait to come back and explore this cute community more in the future!"

Katelyn F.

The price is ￥39,343

￥39,343

￥58,086 total

includes taxes & fees

Oct 7 - Oct 8

Historic Stillwater Home close to downtown

A spacious living room with wooden floors, two sofas, a coffee table, and a large rug.

A cozy living room with a stone fireplace, a foosball table, and a large window offering a view of the outdoors.

A modern kitchen with a marble island, black bar stools, and a wine rack.

A modern kitchen with white cabinets, a marble island, and black bar stools.

18. Woodsy Retreat: Chef's Kitchen, Dance Room & Gym

Woodsy Retreat: Chef's Kitchen, Dance Room & Gym

White Bear Lake

9.4 out of 10, Exceptional, (10 reviews)

9.4/10

Exceptional

(10 reviews)

"House very clean and well stocked."

Brad H.

The price is ￥17,421

￥17,421

￥54,356 total

includes taxes & fees

Oct 13 - Oct 14

Woodsy Retreat: Chef's Kitchen, Dance Room & Gym

A spacious living area with a wooden ceiling, a black leather sectional sofa, a wooden coffee table, and a kitchen in the background.

A kitchen with wooden cabinets, a stainless steel refrigerator, a sink, and a bar stool area.

A living room with a leather sectional sofa, a wooden coffee table, a patterned rug, a staircase, and a dining area with wooden chairs.

A wooden staircase leading to a dock over water, surrounded by trees and greenery.

19. Home with Lake Access (Pontoon available to rent!)

Home with Lake Access (Pontoon available to rent!)

Amery

9.6 out of 10, Exceptional, (33 reviews)

9.6/10

Exceptional

(33 reviews)

"This property was the perfect home base for our family as we hosted our daughter's wedding reception at nearby Amery Ale Works. Extra kindness at every step!"

Jennifer E.

The price is ￥62,948

￥62,948

￥89,809 total

includes taxes & fees

Oct 5 - Oct 6

Home with Lake Access (Pontoon available to rent!)

A spacious kitchen with a large island, wooden cabinets, and a stainless steel refrigerator.

A spacious living room with a gray sectional sofa, a wooden dining table with bar stools, and large windows offering views of the outdoors.

A kitchen with a coffee maker, kettle, and storage drawer.

A spacious living room with hardwood floors, a large flat-screen TV, a wooden entertainment unit, and a staircase leading to another level.

20. CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails

CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails

Stillwater

9.6 out of 10, Exceptional, (14 reviews)

9.6/10

Exceptional

(14 reviews)

"Excellent place to stay. We will definitely be returning. Host was very accommodating."

Judy K.

The price is ￥31,474

￥31,474

￥106,917 total

includes taxes & fees

Oct 5 - Oct 6

CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails

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

River Valley Inn & Suites

10/10 Excellent

"Very quite"

Brock 1-night trip

Posted 12 hours ago

River Valley Inn & Suites

Country Inn & Suites by Radisson, Forest Lake, MN

8/10 Good

"Clean room, good breakfast and large hot tub."

Scott 2-night trip

Posted 16 hours ago

Country Inn & Suites by Radisson, Forest Lake, MN

Holiday Inn Express & Suites Vadnais Heights by IHG

10/10 Excellent

"Great place but the ac unit didn’t work properly and I was hoping to get a discount but since I used a third party, they couldn’t help. Who nowadays can call hotels directly!!"

Brad 3-night trip

Posted 17 hours ago

Holiday Inn Express & Suites Vadnais Heights by IHG

Hotel Crosby

10/10 Excellent

"Great boutique hotel with a great restaurant / bar and comfy shared areas. Location could not be better and the dinner we had was one of the best we've ever had anywhere."

Brian 1-night trip

Posted 18 hours ago

Hotel Crosby

AmericInn by Wyndham White Bear Lake St. Paul

10/10 Excellent

"Will stay again."

Terry 1-night trip

Posted 20 hours ago

AmericInn by Wyndham White Bear Lake St. Paul

Country Inn & Suites by Radisson Stillwater MN

8/10 Good

"Pleasant stay."

Kessler 1-night trip

Posted 21 hours ago

Country Inn & Suites by Radisson Stillwater MN

Water Street Inn

8/10 Good

"Only issue we had was the bed mattress was extremely soft or maybe old. Room was beautiful. Area was beautiful. Mattress was the only concern I have with this place which is an easy fix for them if they find time to either flip or get a new one. Could've just been our room too."

THOR 1-night trip

Posted 1 day ago

Water Street Inn

Historic 1880s Home

10/10 Excellent

"A great place to stay!"

Joe B. 4-night trip

Posted 2 days ago

Historic 1880s Home

Best Western Plus White Bear Country Inn

10/10 Excellent

"The hotel was perfect for our stay. Clean rooms, comfortable beds, friendly staff. The housekeeping staff was especially very helpful and very nice!"

Amy 2-night trip

Posted 3 days ago

Best Western Plus White Bear Country Inn

Find out more about Osceola

Osceola Vacation Homes information

Number of reviews	673
Accommodation	161 Vacation Homes
Lowest Price	￥24,306
Highest Price	￥119,156

Explore a world of travel with Expedia

More ways to book

Book Vacation Homes in Osceola on Expedia.com

Search Vacation Homes in Osceola

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Osceola vacation homes

1. Historic 1880s Home

2. Lovers Lookout 2 at Big Rock Creek

3. Scandinavian Retreat

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

5. Nordic Harbor | Room 5 | Cedar Shadows

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

7. Classic Home

8. Riverside Historic Home near Downtown, Wineries, Hiking

9. Nordic Harbor | Room 1 | Acorn Oak

10. Historic Swedish Cottage on Quiet Lindstrom Lake

11. Nordic Harbor | Room 4 | Nordic Spruce

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

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

14. White Bear Lake House 3 blocks from Downtown and Lake!

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

16. Relaxing Townhouse Escape

17. Historic Stillwater Home close to downtown

18. Woodsy Retreat: Chef's Kitchen, Dance Room & Gym

19. Home with Lake Access (Pontoon available to rent!)

20. CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails

Find vacation rentals that suit your style

Top Osceola Hotel Reviews

River Valley Inn & Suites

Find out more about Osceola

Osceola Vacation Homes information

Explore a world of travel with Expedia