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Osceola Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

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 ￥18,001
￥23,429 total
includes taxes & fees
Jun 17 - Jun 18
Cozy Mother-in-Law Apartment
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 ￥38,450
￥48,324 total
includes taxes & fees
Jun 14 - Jun 15
Historic 1880s Home
Exterior

Lovers Lookout 3 at Big Rock Creek

Lovers Lookout 3 at Big Rock Creek
Saint Croix Falls
10.0 out of 10, Exceptional, (5 reviews)
"We had an amazing time. The set up is so cute and it’s very peaceful. Very comfortable beds and extremely clean. Loved it!"
United States
Jessica O.
The price is ￥18,401
￥31,128 total
includes taxes & fees
Jul 13 - Jul 14
Lovers Lookout 3 at Big Rock Creek
Interior

Home on the Apple River

Home on the Apple River
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 ￥20,641
￥35,620 total
includes taxes & fees
Jun 21 - Jun 22
Home on the Apple River
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, (842 reviews)
"Great local hotel!"
United States
Teresa
The price is ￥12,691
￥14,984 total
includes taxes & fees
Jun 14 - Jun 15
Hudson Inn & Suites
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.
The price is ￥12,641
￥24,714 total
includes taxes & fees
Jun 16 - Jun 17
Lovers Lookout 2 at Big Rock Creek
Terrace/patio

Private Suite in historic Stillwater North Hill

Private Suite in historic Stillwater North Hill
Stillwater
10.0 out of 10, Exceptional, (36 reviews)
"This was the perfect spot for a couple nights in Stillwater. Comfortable bed. Cute decorations. Very clean. The host was very responsive. We hope to stay again when we return for a weekend getaway."
United States
Ronda
The price is ￥24,002
￥44,774 total
includes taxes & fees
Jun 15 - Jun 16
Private Suite in historic Stillwater North Hill
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
9.0 out of 10, Wonderful, (36 reviews)
"Very clear communication, comfortable beds and all the amenities you need for a night stay!"
United States
Farrah S.
The price is ￥15,841
￥29,711 total
includes taxes & fees
Jun 15 - Jun 16
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
Interior

Classic Home

Classic Home
Centuria
8.4 out of 10, Very Good, (37 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 ￥20,001
￥34,607 total
includes taxes & fees
Jun 15 - Jun 16
Classic Home
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 ￥15,841
￥28,259 total
includes taxes & fees
Jun 15 - Jun 16
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge
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 ￥31,842
￥52,669 total
includes taxes & fees
Jun 23 - Jun 24
Lake Home property
Smart TV

Minne-GetAway: Modern Cottage

Minne-GetAway: Modern Cottage
North Saint Paul
9.6 out of 10, Exceptional, (15 reviews)
"Comfortable beds and clean bathrooms."
United States
Angelika
Minne-GetAway: Modern Cottage
Exterior

Historic Stillwater Home close to downtown

Historic Stillwater Home close to downtown
Stillwater
10.0 out of 10, Exceptional, (73 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 ￥40,003
￥59,409 total
includes taxes & fees
Jun 23 - Jun 24
Historic Stillwater Home close to downtown
Smart TV

Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (39 reviews)
"Beautiful place, great location and amazing hosts!!!!"
United States
Dylan M.
The price is ￥31,394
￥64,118 total
includes taxes & fees
Jun 16 - Jun 17
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
9.8 out of 10, Exceptional, (10 reviews)
"Very clean and exactly as described, would stay again! "
United States
Thomas R.
The price is ￥25,346
￥37,203 total
includes taxes & fees
Jun 23 - Jun 24
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC
3 bedrooms, desk, travel crib, WiFi

Peaceful 3-bedroom cabin in charming Amery

Peaceful 3-bedroom cabin in charming Amery
Amery
10.0 out of 10, Exceptional, (2 reviews)
"What a beautiful getaway… Charming, amazing property , very relaxing, just lovely!"
United States
Chris D.
The price is ￥41,603
￥66,513 total
includes taxes & fees
Jun 18 - Jun 19
Peaceful 3-bedroom cabin in charming Amery
Fridge, microwave, oven, stovetop

Cambrian & Co. Loft Cozy, Charming, Downtown Ease

Cambrian & Co. Loft Cozy, Charming, Downtown Ease
Taylors Falls
10.0 out of 10, Exceptional, (15 reviews)
"Good place to stay."
United States
Douglas J.
The price is ￥24,002
￥34,364 total
includes taxes & fees
Jul 5 - Jul 6
Cambrian & Co. Loft Cozy, Charming, Downtown Ease
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 ￥20,001
￥33,594 total
includes taxes & fees
Jun 23 - Jun 24
River road cabin
Smart TV

BestLocation|Romantic|ViewBridgeFromBed|Couples|Pets|Photo backdrop|Nightlife!!!

BestLocation|Romantic|ViewBridgeFromBed|Couples|Pets|Photo backdrop|Nightlife!!!
Stillwater
9.4 out of 10, Exceptional, (59 reviews)
"Enjoyed our stay in stillwater. Host is very responsive and the property is amazing. The location is perfect for a getaway. We have enjoyed the property before and plan too again "
United States
Michael M.
The price is ￥30,082
￥61,151 total
includes taxes & fees
Jun 14 - Jun 15
BestLocation|Romantic|ViewBridgeFromBed|Couples|Pets|Photo backdrop|Nightlife!!!
Dining

Relaxing Townhouse Escape

Relaxing Townhouse Escape
Hugo
9.0 out of 10, Wonderful, (19 reviews)
"Clean & comfortable stay. Great location and appreciated use of the garage for additional parking space. "
United States
Jennifer L.
The price is ￥26,402
￥45,957 total
includes taxes & fees
Jun 21 - Jun 22
Relaxing Townhouse Escape
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

Water Street Inn

Water Street Inn

10/10 Excellent
"Clean room, beautiful view. Friendly staff. "
Heidi 1-night trip
Posted 4 hours ago
Water Street Inn

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

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?

Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park : This vacation home rental outside of Osceola is located on a lake and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.