Osceola Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Osceola vacation rentals

Exterior

Cozy Mother-in-Law Apartment

Cozy Mother-in-Law Apartment
Osceola
10.0 out of 10, Exceptional, (51 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 ￥16,134
￥21,336 total
includes taxes & fees
Apr 21 - Apr 22
Cozy Mother-in-Law Apartment
Interior

Historic 1880s Home

Historic 1880s Home
Osceola
10.0 out of 10, Exceptional, (75 reviews)
"Beautiful home and beautiful vibe. Would visit again!"
United States
Janice
The price is ￥26,985
￥33,853 total
includes taxes & fees
Apr 21 - Apr 22
Historic 1880s Home
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, (820 reviews)
"Great place. Stay there whenever we are in Hudson if they have a room available."
United States
Diana
The price is ￥12,314
￥14,565 total
includes taxes & fees
Apr 22 - Apr 23
Hudson Inn & Suites
Exterior

Romantic getaway! With gorgeous views from the Hot Tub!

Romantic getaway! With gorgeous views from the Hot Tub!
Taylors Falls
9.4 out of 10, Exceptional, (106 reviews)
"The hot tub was beautiful and cozy. Our host was wonderful and responsive. We would recommend staying here . "
United States
Amber C.
The price is ￥13,326
￥45,652 total
includes taxes & fees
May 14 - May 15
Romantic getaway! With gorgeous views from the Hot Tub!
Outdoor dining

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)
"We enjoyed everything about our stay! Just wish we had more time to enjoy the amenities of the property. "
United States
Kim J.
Lovers Lookout 2 at Big Rock Creek
Interior

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

Woodsy Retreat: Chef's Kitchen, Dance Room & Gym
White Bear Lake
10.0 out of 10, Exceptional, (7 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 ￥17,276
￥54,139 total
includes taxes & fees
Apr 19 - Apr 20
Woodsy Retreat: Chef's Kitchen, Dance Room & Gym
Smart TV

Minne-GetAway: Modern Cottage

Minne-GetAway: Modern Cottage
North Saint Paul
9.6 out of 10, Exceptional, (14 reviews)
"Comfortable beds and clean bathrooms."
United States
Angelika
The price is ￥16,448
￥44,991 total
includes taxes & fees
Apr 22 - Apr 23
Minne-GetAway: Modern Cottage
Exterior

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
9.2 out of 10, Wonderful, (35 reviews)
"Very clear communication, comfortable beds and all the amenities you need for a night stay!"
United States
Farrah S.
The price is ￥15,705
￥29,289 total
includes taxes & fees
May 4 - May 5
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
Dining

1 Bdr Cabin duplex unit on Apple River. Kayaks, SUPs & Sauna. Pet friendly!

1 Bdr Cabin duplex unit on Apple River. Kayaks, SUPs & Sauna. Pet friendly!
Amery
9.8 out of 10, Exceptional, (17 reviews)
"It’s was clean and modern. We enjoyed our stay "
United States
Derek K.
The price is ￥17,503
￥29,012 total
includes taxes & fees
Apr 30 - May 1
1 Bdr Cabin duplex unit on Apple River. Kayaks, SUPs & Sauna. Pet friendly!
Terrace/patio

Private Suite in historic Stillwater North Hill

Private Suite in historic Stillwater North Hill
Stillwater
10.0 out of 10, Exceptional, (33 reviews)
"Very welcoming and helpful hosts. Such a cute cozy little loft! We loved it! Very clean! "
United States
Jennifer H.
The price is ￥18,244
￥37,138 total
includes taxes & fees
Apr 19 - Apr 20
Private Suite in historic Stillwater North Hill
Terrace/patio

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
The price is ￥16,867
￥29,277 total
includes taxes & fees
Apr 22 - Apr 23
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
Interior

Home on the Apple River

Home on the Apple River
Amery
10.0 out of 10, Exceptional, (4 reviews)
"Host was very helpful everythig went perfect we had a great time "
United States
Rusty S.
The price is ￥18,244
￥32,303 total
includes taxes & fees
Apr 28 - Apr 29
Home on the Apple River
Exterior

River road cabin

River road cabin
Saint Croix Falls
8.0 out of 10, Very Good, (14 reviews)
"Great stay. Would do it again."
United States
Jeff W.
The price is ￥15,705
￥28,285 total
includes taxes & fees
Apr 21 - Apr 22
River road cabin
Room

Peaceful 3-bedroom cabin in charming Amery

Peaceful 3-bedroom cabin in charming Amery
Amery
The price is ￥18,617
￥38,443 total
includes taxes & fees
Apr 21 - Apr 22
Peaceful 3-bedroom cabin in charming Amery
Interior

Classic Home

Classic Home
Centuria
8.4 out of 10, Very Good, (36 reviews)
"Perfect place for our needs. Clean. Easy check in process. Host was great at communicating. "
United States
Northwoods C.
The price is ￥19,830
￥34,311 total
includes taxes & fees
May 17 - May 18
Classic Home
Dining

Eleanor - 2 bdr Cabin Duplex unit-River-SUPS, Kayaks, & Sauna! Pet friendly!

Eleanor - 2 bdr Cabin Duplex unit-River-SUPS, Kayaks, & Sauna! Pet friendly!
Amery
9.6 out of 10, Exceptional, (15 reviews)
"Very clean, comfortable cabin, beautiful area, nice fire pit area, love the large soaking tub! "
United States
Deb P.
The price is ￥20,765
￥34,024 total
includes taxes & fees
Apr 20 - Apr 21
Eleanor - 2 bdr Cabin Duplex unit-River-SUPS, Kayaks, & Sauna! Pet friendly!
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

Nordic Harbor | Room 4 | Nordic Spruce

Nordic Harbor | Room 4 | Nordic Spruce
Center City
The price is ￥38,074
￥49,299 total
includes taxes & fees
Apr 30 - May 1
Nordic Harbor | Room 4 | Nordic Spruce
Outdoor dining

Lovers Lookout 1: Where Rustic Meets Luxury at Big Rock Creek

Lovers Lookout 1: Where Rustic Meets Luxury at Big Rock Creek
Saint Croix Falls
10.0 out of 10, Exceptional, (1 review)
"Everything was clean and nice when we arrived. Check in was easy by text. We were greatedby the owners not long after check in and they delivered us firewood that we purchased. Was an amazing stay and we hope to come back every year !"
United States
Jenny E.
The price is ￥17,292
￥29,523 total
includes taxes & fees
May 19 - May 20
Lovers Lookout 1: Where Rustic Meets Luxury at Big Rock Creek
Exterior

Historic Stillwater Home close to downtown

Historic Stillwater Home close to downtown
Stillwater
10.0 out of 10, Exceptional, (69 reviews)
"We enjoyed the location and amenities of this home. Our group of 4 adults and 3 infants were able to spread out and sleep comfortably, the house write up was accurate and the homey touches provided a wonderful space to relax and reconnect. We enjoyed our stay!"
United States
Crystal R.
The price is ￥35,694
￥53,547 total
includes taxes & fees
Apr 19 - Apr 20
Historic Stillwater Home close to downtown
Exterior

Lake Home property

Lake Home property
Luck
9.6 out of 10, Exceptional, (13 reviews)
"Very nice cozy cabin and such a great, accommodating host! "
United States
Jesse S.
The price is ￥23,637
￥42,510 total
includes taxes & fees
Apr 21 - Apr 22
Lake Home property
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

Hotel Crosby

Hotel Crosby

10/10 Excellent
"Love it all beautiful bar and amazing hot tub. Beautiful rooms"
Jolyt 2-night trip
Posted 1 hour ago
Hotel Crosby

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:

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Frequently asked questions

Can I find a vacation rental in Osceola?

Yes, you can find vacation rentals in Osceola near Osceola & St. Croix Valley Railway, or you can go with a secluded option if you're looking for extra privacy while you relax. 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 vacation home rentals that Osceola has to offer?

Stillwater's Third Street Inn: This vacation home rental outside of Osceola offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Osceola?

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

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 vacation rentals like in Osceola?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Osceola. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.