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

Osceola Holiday Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Osceola holiday rentals

Interior

Historic 1880s Home

Historic 1880s Home
Osceola
10.0 out of 10, Exceptional, (79 reviews)
"Perfect location, very clean and charming house, comfortable beds and very well stocked kitchen and home"
United States
Amy G.
The price is HK$1,899
HK$2,367 total
includes taxes & fees
7 Jul - 8 Jul
Historic 1880s Home
Exterior

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 HK$946
HK$1,219 total
includes taxes & fees
7 Jul - 8 Jul
Cozy Mother-in-Law Apartment
Desk, iron/ironing board, free WiFi, bed sheets

Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very good, (852 reviews)
"Great local hotel!"
United States
Teresa
The price is HK$641
HK$755 total
includes taxes & fees
5 Jul - 6 Jul
Hudson Inn & Suites
Exterior

Historic Stillwater Home close to downtown

Historic Stillwater Home close to downtown
Stillwater
10.0 out of 10, Exceptional, (77 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!"
United States
Katelyn F.
The price is HK$1,961
HK$2,869 total
includes taxes & fees
8 Jul - 9 Jul
Historic Stillwater Home close to downtown
Interior

Luxurious remodel near historic downtown Hudson!

Luxurious remodel near historic downtown Hudson!
Hudson
10.0 out of 10, Exceptional, (32 reviews)
"Great place to stay! We loved it."
United States
Emily Z.
Luxurious remodel near historic downtown Hudson!
Interior

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

Woodsy Retreat: Chef's Kitchen, Dance Room & Gym
White Bear Lake
9.6 out of 10, Exceptional, (9 reviews)
"Fantastic home with ample kitchen space and everything you need to prepare meals. Has a great layout and amenities for entertaining. We thoroughly enjoyed our stay and would visit again!"
United States
Drew R.
The price is HK$1,271
HK$3,188 total
includes taxes & fees
6 Jul - 7 Jul
Woodsy Retreat: Chef's Kitchen, Dance Room & Gym
Property grounds

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$1,882
HK$2,437 total
includes taxes & fees
15 Jul - 16 Jul
Nordic Harbor | Room 5 | Cedar Shadows
Fridge, microwave, oven, stovetop

Gorgeous 5 bed Remodel near Downtown Hudson for Groups!

Gorgeous 5 bed Remodel near Downtown Hudson for Groups!
Hudson
10.0 out of 10, Exceptional, (11 reviews)
"This home was an excellent place to stay. The beds were super comfortable and everything in the home was very clean. We would definitely stay here again. Great communication with the host."
United States
Elizabeth F.
Gorgeous 5 bed Remodel near Downtown Hudson for Groups!
Exterior detail

Just built 3-bedroom Scandinavian loft cottage near Lindstrom-Taylor's Falls

Just built 3-bedroom Scandinavian loft cottage near Lindstrom-Taylor's Falls
center city
10.0 out of 10, Exceptional, (1 review)
"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!"
United States
Karen M.
The price is HK$2,330
HK$3,807 total
includes taxes & fees
8 Jul - 9 Jul
Just built 3-bedroom Scandinavian loft cottage near Lindstrom-Taylor's Falls
Exterior

3-bedroom house in charming Stillwater with AC

3-bedroom house in charming Stillwater with AC
Stillwater
9.6 out of 10, Exceptional, (15 reviews)
"The neighborhood and home were lovely. Inside, the home was very clean and comfortable, and the kitchen had everything we needed. We'd definitely stay here again!"
United States
Amanda S.
The price is HK$1,941
HK$4,283 total
includes taxes & fees
6 Jul - 7 Jul
3-bedroom house in charming Stillwater with AC
Smart TV

Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (40 reviews)
"Beautiful place, great location and amazing hosts!!!!"
United States
Dylan M.
The price is HK$1,737
HK$3,370 total
includes taxes & fees
5 Jul - 6 Jul
Scandinavian Retreat
Exterior detail

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, (12 reviews)
"Very clean and exactly as described, would stay again! "
United States
Thomas R.
The price is HK$1,362
HK$1,974 total
includes taxes & fees
6 Jul - 7 Jul
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC
Outdoor dining

Nordic Harbor | Room 3 | Arctic Pine - Suite

Nordic Harbor | Room 3 | Arctic Pine - Suite
Center City
10.0 out of 10, Exceptional, (1 review)
"Beautiful place and will be staying there again. "
United States
SUZANNE M.
The price is HK$2,745
HK$3,525 total
includes taxes & fees
15 Jul - 16 Jul
Nordic Harbor | Room 3 | Arctic Pine - Suite
Property grounds

Balsam Lake Sunset Cabin with WiFi & Sauna!

Balsam Lake Sunset Cabin with WiFi & Sauna!
Balsam Lake
9.6 out of 10, Exceptional, (47 reviews)
"I had my out of town family stay here and it was just perfect. It's a great location on the lake, easy to get to both by boat and land."
United States
Kris M.
The price is HK$5,490
HK$10,384 total
includes taxes & fees
31 Jul - 1 Aug
Balsam Lake Sunset Cabin with WiFi & Sauna!
Exterior

Lake Home property

Lake Home property
Luck
9.2 out of 10, Wonderful, (14 reviews)
"Very nice cozy cabin and such a great, accommodating host! "
United States
Jesse S.
The price is HK$1,561
HK$2,582 total
includes taxes & fees
8 Jul - 9 Jul
Lake Home property
Living area

Spacious light-filled house near Stillwater - The Stone's Throw Riverhouse

Spacious light-filled house near Stillwater - The Stone's Throw Riverhouse
Stillwater
9.4 out of 10, Exceptional, (18 reviews)
"Our stay was work related . We enjoyed the large space and convience for our location."
United States
Beth
The price is HK$2,235
HK$6,200 total
includes taxes & fees
6 Jul - 7 Jul
Spacious light-filled house near Stillwater - The Stone's Throw Riverhouse
Dining

Relaxing Townhouse Escape

Relaxing Townhouse Escape
Hugo
9.0 out of 10, Wonderful, (20 reviews)
"Clean & comfortable stay. Great location and appreciated use of the garage for additional parking space. "
United States
Jennifer L.
The price is HK$1,294
HK$2,261 total
includes taxes & fees
26 Jul - 27 Jul
Relaxing Townhouse Escape
Fridge, microwave, oven, stovetop

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
9.8 out of 10, Exceptional, (12 reviews)
"Excellent place to stay. We will definitely be returning. Host was very accommodating."
United States
Judy K.
The price is HK$1,788
HK$5,644 total
includes taxes & fees
6 Jul - 7 Jul
CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails
Interior

Classic Home

Classic Home
Centuria
8.2 out of 10, Very good, (38 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$980
HK$1,754 total
includes taxes & fees
9 Jul - 10 Jul
Classic Home
Interior

Apple River Retreat home in Amery

Apple River Retreat home in Amery
Amery
10.0 out of 10, Exceptional, (5 reviews)
"Host was very helpful everythig went perfect we had a great time "
United States
Rusty S.
The price is HK$1,090
HK$1,920 total
includes taxes & fees
27 Jul - 28 Jul
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.
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Top Osceola Hotel Reviews

Hudson Inn & Suites

Hudson Inn & Suites

10/10 Excellent
"such a great location. would stay again"
michele 2-night trip
Posted 22 hours ago
Hudson Inn & Suites

Find out more about Osceola

Search for holiday rentals in Osceola on Expedia! You can easily find your home rentals, villas, holiday apartments in Osceola using one of the methods below:

  • View our selection of featured holiday rentals in Osceola
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  • Enter your travel dates to view the best deals on holiday rentals in Osceola while they last

Look no further and take a look at our great range of rental properties in Osceola!

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?

MINNeSTAY* St. Croix Valley Inn: This highly rated holiday home rental in Osceola is located on the waterfront, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Osceola?

Choose from 6 Expedia holiday rentals in Osceola for a memorable holiday.

What can I see and do in Osceola?

Saint Croix River and Apple 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.