Holiday Rentals in Osceola

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Our top choices for Osceola holiday 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.
The price is €115
includes taxes & fees
11 May - 12 May
Cozy Mother-in-Law Apartment

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 €191
includes taxes & fees
11 May - 12 May
Historic 1880s Home

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 €183
includes taxes & fees
11 May - 12 May
Eleanor - 2 bdr Cabin Duplex unit-River-SUPS, Kayaks, & Sauna! Pet friendly!

Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very good, (824 reviews)
"Comfy and clean. "
United States
Melissa
The price is €82
includes taxes & fees
11 May - 12 May
Hudson Inn & Suites

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 €160
includes taxes & fees
12 May - 13 May
1 Bdr Cabin duplex unit on Apple River. Kayaks, SUPs & Sauna. Pet friendly!

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 €135
includes taxes & fees
11 May - 12 May
Lovers Lookout 2 at Big Rock Creek

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 €234
includes taxes & fees
13 May - 14 May
Lake Home property

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 €298
includes taxes & fees
11 May - 12 May
Scandinavian Retreat

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.
The price is €229
includes taxes & fees
12 May - 13 May
Private Suite in historic Stillwater North Hill

Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm

Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
Taylors Falls
9.8 out of 10, Exceptional, (9 reviews)
"Very conveniently located to downtown Taylors Falls and Interstate Park so we could walk everywhere!"
United States
Allison G.
The price is €184
includes taxes & fees
11 May - 12 May
Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm

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 €160
includes taxes & fees
25 May - 26 May
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

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 €286
includes taxes & fees
11 May - 12 May
Historic Stillwater Home close to downtown

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 €178
includes taxes & fees
11 May - 12 May
River road cabin

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 €183
includes taxes & fees
17 May - 18 May
Classic Home

Peaceful 3-bedroom cabin in charming Amery

Peaceful 3-bedroom cabin in charming Amery
Amery
10.0 out of 10, Exceptional, (1 review)
"Cabin was awesome! Loved the big screened in porch to sit and watch the river and wildlife. Would love to come back here. "
United States
Brian P.
The price is €237
includes taxes & fees
12 May - 13 May
Peaceful 3-bedroom cabin in charming Amery

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, (9 reviews)
"Very clean and exactly as described, would stay again! "
United States
Thomas R.
The price is €194
includes taxes & fees
11 May - 12 May
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC

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 €498
includes taxes & fees
11 May - 12 May
Midcentury Lake Home!

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 €189
includes taxes & fees
17 May - 18 May
Home on the Apple River

Nordic Harbor | Room 1 | Acorn Oak

Nordic Harbor | Room 1 | Acorn Oak
Center City
10.0 out of 10, Exceptional, (2 reviews)
"Our stay was wonderful---quaint, modern-rustic and very comfortable. We loved being able to walk across the parking lot to the rooftop bar."
United States
Alisha H.
The price is €265
includes taxes & fees
11 May - 12 May
Nordic Harbor | Room 1 | Acorn Oak

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 €326
includes taxes & fees
17 May - 18 May
BestLocation|Romantic|ViewBridgeFromBed|Couples|Pets|Photo backdrop|Nightlife!!!
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osceola holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Osceola holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osceola holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osceola holiday rentals we have selected for you start as low as €82 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Osceola rentals

At Expedia, we put the best Osceola holiday 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 holiday.

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 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?

Cozy Lodge Theme Home in Beautiful Hudson, WI: This holiday home rental outside of Osceola is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a garden.

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?

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 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.