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

Search Vacation Homes 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
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 homes

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, (86 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 HK$1,405
HK$1,753 total
includes taxes & fees
25 Oct - 26 Oct
Historic 1880s Home
A modern living room with a spiral staircase, a sofa set, a coffee table, and a chandelier.

2. 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 HK$1,391
HK$3,045 total
includes taxes & fees
27 Oct - 28 Oct
Scandinavian Retreat
A wooden deck with outdoor seating, overlooking a body of water.

3. Nordic Harbor | Room 5 | Cedar Shadows

Nordic Harbor | Room 5 | Cedar Shadows
Center City
9.8 out of 10, Exceptional, (10 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 HK$1,883
HK$2,438 total
includes taxes & fees
26 Oct - 27 Oct
Nordic Harbor | Room 5 | Cedar Shadows
A two-story house with a wooden deck, large windows, and a covered porch area.

4. 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 HK$1,766
HK$3,197 total
includes taxes & fees
1 Nov - 2 Nov
Scandinavian loft Lindstrom-Taylor's Falls with private hot tub year round.
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.

5. Riverside Historic Home near Downtown, Wineries, Hiking

Riverside Historic Home near Downtown, Wineries, Hiking
Taylors Falls
10.0 out of 10, Exceptional, (22 reviews)
"Very smooth and easy stay. Home was well thought out and instructions for everything were very well laid out. "
United States
Elite Motorsports
The price is HK$1,942
HK$4,777 total
includes taxes & fees
25 Oct - 26 Oct
Riverside Historic Home near Downtown, Wineries, Hiking
A wooden cabin with a triangular roof, a central door, and a small window.

6. 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 A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
A kitchen with wooden cabinets, a granite countertop, a window with a faucet, and a black doormat.

7. 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 HK$981
HK$1,788 total
includes taxes & fees
29 Oct - 30 Oct
Classic Home
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 HK$1,883
HK$2,430 total
includes taxes & fees
28 Oct - 29 Oct
Nordic Harbor | Room 1 | Acorn Oak
Relax on Our Porch Swing

9. 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 HK$3,335
HK$5,941 total
includes taxes & fees
29 Oct - 30 Oct
Historic Swedish Cottage on Quiet Lindstrom Lake
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.

10. 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 HK$2,034
HK$2,618 total
includes taxes & fees
1 Nov - 2 Nov
Nordic Harbor | Room 2 | Tranquil Maple
A compact kitchen with a microwave, a sink, and a small countertop.

11. Nordic Harbor | Room 4 | Nordic Spruce

Nordic Harbor | Room 4 | Nordic Spruce
Center City
The price is HK$1,883
HK$2,421 total
includes taxes & fees
22 Nov - 23 Nov
Nordic Harbor | Room 4 | Nordic Spruce
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)
"Very clear communication, comfortable beds and all the amenities you need for a night stay!"
United States
Farrah S.
The price is HK$981
HK$1,780 total
includes taxes & fees
17 Nov - 18 Nov
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
A covered outdoor patio with a table, chairs, and a bench.

13. 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 HK$2,746
HK$3,538 total
includes taxes & fees
21 Nov - 22 Nov
Nordic Harbor | Room 6 | Silver Birch - Suite
A room with a large window, a flat-screen TV, and a wooden cabinet.

14. 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 HK$2,296
HK$4,600 total
includes taxes & fees
26 Oct - 27 Oct
Scenic Apple River Retreat - Spacious 4BR Home - Fishing, Tubing & Kayaking
Fireplace

15. Escape to The Clubhouse, St. Croix Falls city, Wisconsin

Escape to The Clubhouse, St. Croix Falls city, Wisconsin
Saint Croix Falls
The price is HK$6,208
HK$7,485 total
includes taxes & fees
8 Nov - 9 Nov
Escape to The Clubhouse, St. Croix Falls city, Wisconsin
A spacious living area with a wooden ceiling, a black leather sectional sofa, a wooden coffee table, and a kitchen in the background.

16. 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)
"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!"
United States
Jennifer E.
The price is HK$3,139
HK$4,511 total
includes taxes & fees
21 Nov - 22 Nov
Home with Lake Access (Pontoon available to rent!)
A house with a large porch, outdoor seating, and a fire pit.

17. Escape to The Clubhouse at Big Rock Creek – Your All-Season Adventure Awaits!

Escape to The Clubhouse at Big Rock Creek – Your All-Season Adventure Awaits!
St. Croix
9.6 out of 10, Exceptional, (26 reviews)
"Great for families to play and visit , felt very safe here !"
United States
Karen P.
The price is HK$3,876
HK$6,692 total
includes taxes & fees
8 Nov - 9 Nov
Escape to The Clubhouse at Big Rock Creek – Your All-Season Adventure Awaits!
A spacious living room with wooden floors, two sofas, a coffee table, and a large rug.

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)
"House very clean and well stocked."
United States
Brad H.
The price is HK$855
HK$2,695 total
includes taxes & fees
26 Oct - 27 Oct
Woodsy Retreat: Chef's Kitchen, Dance Room & Gym
A dining area with a wooden table, grey upholstered chairs, and a tray with beverages and snacks.

19. Relaxing Townhouse Escape

Relaxing Townhouse Escape
Hugo
9.2 out of 10, Wonderful, (27 reviews)
"Nice clean place. Perfect for what we needed."
United States
Sara C.
Relaxing Townhouse Escape
A two-story house with a front porch, brick facade, and a garage.

20. Historic Stillwater Home close to downtown

Historic Stillwater Home close to downtown
Stillwater
10.0 out of 10, Exceptional, (89 reviews)
"The house was perfect and nice and close to downtown Stillwater!"
United States
Tyler R.
The price is HK$1,962
HK$2,913 total
includes taxes & fees
26 Oct - 27 Oct
Historic Stillwater Home close to downtown
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

Water Street Inn

Water Street Inn

10/10 Excellent
"What a beautiful property! Only here for a night but the young man who checked us in was wonderful and got us a room a little early. Perfect location for a night and some shopping in Stillwater"
LAURA 1-night trip
Posted 6 hours ago
Water Street Inn

Find out more about Osceola

Osceola Vacation Homes information

Number of reviews
613
Accommodation
159 Vacation Homes
Lowest Price
HK$1,753
Highest Price
HK$7,485

Explore a world of travel with Expedia