Osceola Vacation Rentals

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Our top choices for Osceola vacation rentals

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 CA $271
CA $337 total
includes taxes & fees
May 25 - May 26
Historic 1880s Home

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 CA $156
CA $203 total
includes taxes & fees
May 21 - May 22
Cozy Mother-in-Law Apartment

Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very good, (831 reviews)
"Nice place, good location."
United States
john
The price is CA $100
CA $119 total
includes taxes & fees
May 18 - May 19
Hudson Inn & Suites

Private 3bdr cabin on Apple River kayaks, SUPS, & Sauna. Pet friendly!

Private 3bdr cabin on Apple River kayaks, SUPS, & Sauna. Pet friendly!
Amery
9.8 out of 10, Exceptional, (8 reviews)
"House was perfect for our group of five. Very clean, well appointed and great location (convenient to everything local). "
United States
Jesse L.
The price is CA $297
CA $547 total
includes taxes & fees
May 18 - May 19
Private 3bdr cabin on Apple River kayaks, SUPS, & Sauna. Pet friendly!

Historic Stillwater Home close to downtown

Historic Stillwater Home close to downtown
Stillwater
10.0 out of 10, Exceptional, (70 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 CA $309
CA $466 total
includes taxes & fees
May 20 - May 21
Historic Stillwater Home close to downtown

Historic Swedish Cottage on Quiet Lindstrom Lake

Historic Swedish Cottage on Quiet Lindstrom Lake
Lindstrom
9.4 out of 10, Exceptional, (239 reviews)
"Great stay, beautiful views, comfortable. and clean."
United States
CHRISTOPHER
The price is CA $584
CA $1,013 total
includes taxes & fees
May 18 - May 19
Historic Swedish Cottage on Quiet Lindstrom Lake

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

Luxurious remodel near historic downtown Hudson!

Luxurious remodel near historic downtown Hudson!
Hudson
10.0 out of 10, Exceptional, (31 reviews)
"House was very clean and welcoming! Will stay again if possible!"
United States
Jason P.
The price is CA $542
CA $668 total
includes taxes & fees
May 18 - May 19
Luxurious remodel near historic downtown Hudson!

Nordic Harbor | Room 5 | Cedar Shadows

Nordic Harbor | Room 5 | Cedar Shadows
Center City
9.8 out of 10, Exceptional, (8 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 CA $330
CA $424 total
includes taxes & fees
May 19 - May 20
Nordic Harbor | Room 5 | Cedar Shadows

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 CA $177
CA $300 total
includes taxes & fees
Jun 7 - Jun 8
Home on the Apple River

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
9.6 out of 10, Exceptional, (18 reviews)
"It was a perfect cozy cabin with updated amenities. Had a great stay!"
United States
Carissa S.
The price is CA $162
CA $264 total
includes taxes & fees
May 19 - May 20
1 Bdr Cabin duplex unit on Apple River. Kayaks, SUPs & Sauna. Pet friendly!

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.
The price is CA $1,211
CA $1,502 total
includes taxes & fees
May 18 - May 19
Gorgeous 5 bed Remodel near Downtown Hudson for Groups!

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 CA $172
CA $296 total
includes taxes & fees
May 19 - May 20
Classic Home

Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (39 reviews)
"Amazing place! Super cute and close to lots of attractions. Hosts were great communicating and providing a welcoming stay with clear instructions. "
United States
Olivia W.
The price is CA $218
CA $491 total
includes taxes & fees
May 19 - May 20
Scandinavian Retreat

Midcentury Lake Home!

Midcentury Lake Home!
White Bear Lake
8.6 out of 10, Excellent, (25 reviews)
"Comfortable with great location. Would definitely stay here again. "
United States
Mark A.
The price is CA $275
CA $815 total
includes taxes & fees
May 18 - May 19
Midcentury Lake Home!

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 CA $481
CA $619 total
includes taxes & fees
May 18 - May 19
Nordic Harbor | Room 3 | Arctic Pine - Suite

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, (8 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 CA $149
CA $472 total
includes taxes & fees
May 19 - May 20
Woodsy Retreat: Chef's Kitchen, Dance Room & Gym

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, (7 reviews)
"Excellent place to stay. We will definitely be returning. Host was very accommodating."
United States
Judy K.
The price is CA $248
CA $895 total
includes taxes & fees
May 18 - May 19
CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails

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 CA $213
CA $377 total
includes taxes & fees
May 18 - May 19
Lake Home property

MainStreetLocation|GirlsNight|Families|Pets|FoodMusicShopArtExploreBikeFunPlay!!

MainStreetLocation|GirlsNight|Families|Pets|FoodMusicShopArtExploreBikeFunPlay!!
Stillwater
9.4 out of 10, Exceptional, (101 reviews)
"Great location for girls' weekend"
United States
Diane H.
The price is CA $274
CA $540 total
includes taxes & fees
May 31 - Jun 1
MainStreetLocation|GirlsNight|Families|Pets|FoodMusicShopArtExploreBikeFunPlay!!
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

Find out more about Osceola

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Osceola. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Get away from it all and relax on the lake!: This vacation home rental outside of Osceola is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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?

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 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.