Osceola Holiday Rentals

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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 NZ$225
includes taxes & fees
28 Apr - 29 Apr
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 NZ$363
includes taxes & fees
28 Apr - 29 Apr
Historic 1880s Home

Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very good, (822 reviews)
"Comfy and clean. "
United States
Melissa
The price is NZ$149
includes taxes & fees
28 Apr - 29 Apr
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.
The price is NZ$362
includes taxes & fees
29 Apr - 30 Apr
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’s was clean and modern. We enjoyed our stay "
United States
Derek K.
The price is NZ$310
includes taxes & fees
30 Apr - 1 May
1 Bdr Cabin duplex unit on Apple River. Kayaks, SUPs & Sauna. Pet friendly!

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 NZ$458
includes taxes & fees
5 May - 6 May
Romantic getaway! With gorgeous views from the Hot Tub!

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 NZ$465
includes taxes & fees
4 May - 5 May
Lake Home property

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 NZ$312
includes taxes & fees
28 Apr - 29 Apr
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

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 NZ$263
includes taxes & fees
11 May - 12 May
Lovers Lookout 2 at Big Rock Creek

Private Suite in historic Stillwater North Hill

Private Suite in historic Stillwater North Hill
Stillwater
10.0 out of 10, Exceptional, (34 reviews)
"Very welcoming and helpful hosts. Such a cute cozy little loft! We loved it! Very clean! "
United States
Jennifer H.
The price is NZ$396
includes taxes & fees
28 Apr - 29 Apr
Private Suite in historic Stillwater North Hill

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 NZ$576
includes taxes & fees
29 Apr - 30 Apr
Woodsy Retreat: Chef's Kitchen, Dance Room & Gym

Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (37 reviews)
"Cozy stay and convenient location. We were happy. "
United States
Taylor S.
The price is NZ$599
includes taxes & fees
28 Apr - 29 Apr
Scandinavian Retreat

Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm

Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm
Taylors Falls
9.8 out of 10, Exceptional, (8 reviews)
"Very conveniently located to downtown Taylors Falls and Interstate Park so we could walk everywhere!"
United States
Allison G.
The price is NZ$360
includes taxes & fees
28 Apr - 29 Apr
Cambrian & Co. Downtown Loft Stylish, Sophisticated, Charm

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.
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC

Where Comfort Meets Adventure — In Every Season!

Where Comfort Meets Adventure — In Every Season!
Saint Croix Falls
9.8 out of 10, Exceptional, (41 reviews)
"We enjoyed our stay so much! There is a lot to do around the area and our cabin was cozy & relaxing. Thank you!"
United States
Pwggy D.
The price is NZ$477
includes taxes & fees
29 Apr - 30 Apr
Where Comfort Meets Adventure — In Every Season!

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 NZ$298
includes taxes & fees
28 Apr - 29 Apr
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge

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 NZ$353
includes taxes & fees
3 May - 4 May
River road cabin

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 NZ$567
includes taxes & fees
28 Apr - 29 Apr
Historic Stillwater Home close to downtown

3-bedroom house in charming Stillwater with AC

3-bedroom house in charming Stillwater with AC
Stillwater
9.8 out of 10, Exceptional, (13 reviews)
"The neighborhood and home were lovely. Inside, the home was very clean and comfortable, and the kitchen had everything we needed. We'd definitely stay here again!"
United States
Amanda S.
The price is NZ$785
includes taxes & fees
28 Apr - 29 Apr
3-bedroom house in charming Stillwater with AC

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 NZ$639
includes taxes & fees
30 Apr - 1 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, 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 NZ$149 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?

Stillwater's Third Street Inn: This holiday 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 that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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.