Osceola Vacation Rentals

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Our top choices for Osceola vacation rentals

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.
$130 nightly
The price is $143
May 26 - May 27
Total with taxes and fees
Cozy Mother-in-Law Apartment

Historic 1880s Home

Historic 1880s Home
Osceola
10.0 out of 10, Exceptional, (76 reviews)
"Beautiful home and beautiful vibe. Would visit again!"
United States
Janice
$212 nightly
The price is $234
May 25 - May 26
Total with taxes and fees
Historic 1880s Home

Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very Good, (835 reviews)
"Great local hotel!"
United States
Teresa
$83 nightly
The price is $90
Jun 3 - Jun 4
Total with taxes and fees
Hudson Inn & Suites

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.
$206 nightly
The price is $228
May 26 - May 27
Total with taxes and fees
Eleanor - 2 bdr Cabin Duplex unit-River-SUPS, Kayaks, & Sauna! Pet friendly!

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.
$188 nightly
The price is $208
May 25 - May 26
Total with taxes and fees
1 Bdr Cabin duplex unit on Apple River. Kayaks, SUPs & Sauna. Pet friendly!

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.
$209 nightly
The price is $230
May 24 - May 25
Total with taxes and fees
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC

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.
$207 nightly
The price is $218
May 25 - May 26
Total with taxes and fees
Home on the Apple River

Historic Stillwater Home close to downtown

Historic Stillwater Home close to downtown
Stillwater
10.0 out of 10, Exceptional, (72 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.
$314 nightly
The price is $342
May 25 - May 26
Total with taxes and fees
Historic Stillwater Home close to downtown

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.
$530 nightly
The price is $563
May 26 - May 27
Total with taxes and fees
Escape to The Clubhouse at Big Rock Creek – Your All-Season Adventure Awaits!

Nordic Harbor | Room 5 | Cedar Shadows

Nordic Harbor | Room 5 | Cedar Shadows
Center City
9.8 out of 10, Exceptional, (9 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.
$283 nightly
The price is $311
May 24 - May 25
Total with taxes and fees
Nordic Harbor | Room 5 | Cedar Shadows

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.
$334 nightly
The price is $367
May 25 - May 26
Total with taxes and fees
Scandinavian Retreat

Historic Swedish Cottage on Quiet Lindstrom Lake

Historic Swedish Cottage on Quiet Lindstrom Lake
Lindstrom
9.4 out of 10, Exceptional, (240 reviews)
"Great stay, beautiful views, comfortable. and clean."
United States
CHRISTOPHER
$686 nightly
The price is $737
May 25 - May 26
Total with taxes and fees
Historic Swedish Cottage on Quiet Lindstrom Lake

Classic Home

Classic Home
Centuria
8.4 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
$203 nightly
The price is $214
May 24 - May 25
Total with taxes and fees
Classic Home

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.
$261 nightly
The price is $275
May 25 - May 26
Total with taxes and fees
Lake Home property

Private Suite in historic Stillwater North Hill

Private Suite in historic Stillwater North Hill
Stillwater
10.0 out of 10, Exceptional, (35 reviews)
"The hosts were super accommodating and made a last minute booking happen! The space is super cute and just what I needed. I also loved how close it was to downtown Stillwater "
United States
Courtney E.
$246 nightly
The price is $268
May 25 - May 26
Total with taxes and fees
Private Suite in historic Stillwater North Hill

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.
$352 nightly
The price is $383
May 25 - May 26
Total with taxes and fees
BestLocation|Romantic|ViewBridgeFromBed|Couples|Pets|Photo backdrop|Nightlife!!!

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.
$407 nightly
The price is $446
May 31 - Jun 1
Total with taxes and fees
Nordic Harbor | Room 3 | Arctic Pine - Suite

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.
$235 nightly
The price is $247
May 26 - May 27
Total with taxes and fees
Peaceful 3-bedroom cabin in charming Amery

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.
$362 nightly
The price is $400
May 26 - May 27
Total with taxes and fees
Private 3bdr cabin on Apple River kayaks, SUPS, & Sauna. Pet friendly!
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

Everything you need to know about Osceola vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osceola vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osceola vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osceola vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osceola. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Osceola in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osceola rentals

At Expedia, we put the best Osceola vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osceola rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osceola vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osceola. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.