Osceola Holiday Rentals

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Holiday Rentals in Osceola

Historic 1880s Home

Osceola
10.0 out of 10, Exceptional, (69)
"The Property was all and more as it was described on VRBO! Very clean, spacious and comfortable for a friend's weekend. Would highly recommend staying here!!"
United States
Debbie C.
The price is NZ$392
includes taxes & fees
14 Dec - 15 Dec
Historic 1880s Home

Hudson Inn & Suites

3.0 star property
Hudson
8.2 out of 10, Very good, (807)
"Nice property offering a descent stay at "
United States
Kimberly
The price is NZ$156
includes taxes & fees
14 Dec - 15 Dec
Hudson Inn & Suites

Gathering families, friends, & coworkers

Clear Lake
9.8 out of 10, Exceptional, (39)
"Was a great place to stay for our family reunion. Roomy and excellent kitchen/dining area to serve meals for our large family. Large outside play area for kids games!"
United States
Mary L.
Gathering families, friends, & coworkers

Luxe Lakefront Estate near Minneapolis, Hot Tub, Sauna, Kayaks, Sleeps up to 20

Baldwin
10.0 out of 10, Exceptional, (5)
"We stayed here for our wedding weekend with the bridal party. It was an awesome place, well kept and clean and everyone enjoyed their time!! Thank you!"
United States
Ryan L.
Luxe Lakefront Estate near Minneapolis, Hot Tub, Sauna, Kayaks, Sleeps up to 20

Historic Stillwater Home close to downtown

Stillwater
10.0 out of 10, Exceptional, (63)
"Had wonderful stay, location was great with easy access to entertainment and dining. Amenities were perfect."
United States
Thomas K.
The price is NZ$584
includes taxes & fees
9 Dec - 10 Dec
Historic Stillwater Home close to downtown

Historic James Mulvey Carriage house (Whole house)

Stillwater
9.8 out of 10, Exceptional, (34)
"Wonderful stay. Loved the pool!"
United States
Wendy H.
The price is NZ$1,427
includes taxes & fees
9 Dec - 10 Dec
Historic James Mulvey Carriage house (Whole house)

Romantic getaway! With gorgeous views from the Hot Tub!

Taylors Falls
9.4 out of 10, Exceptional, (102)
"Very peaceful and relaxing basement apartment. We were very comfortable for our 6 night stay. "
United States
Laura B.
The price is NZ$456
includes taxes & fees
9 Dec - 10 Dec
Romantic getaway! With gorgeous views from the Hot Tub!

Lakefront, Hot Tub, Golf, Kayaks, ATV, Snowmobile Trails, St.Croix Casino

Turtle Lake
10.0 out of 10, Exceptional, (15)
"Great place to stay and in quiet setting! "
United States
Steve G.
Lakefront, Hot Tub, Golf, Kayaks, ATV, Snowmobile Trails, St.Croix Casino

Park Place Cottage

Mahtomedi
9.6 out of 10, Exceptional, (37)
"Good place. cozy and comfortable"
United States
Jesse L.
Park Place Cottage

Historic Swedish Cottage on Quiet Lindstrom Lake

Lindstrom
9.4 out of 10, Exceptional, (232)
"Nice place and close to wedding venue where my daughter got married this weekend"
United States
Derek G.
The price is NZ$1,275
includes taxes & fees
9 Dec - 10 Dec
Historic Swedish Cottage on Quiet Lindstrom Lake

Private Suite in historic Stillwater North Hill

Stillwater
9.8 out of 10, Exceptional, (30)
"The hosts and place were fantastic all around! "
United States
Tabitha B.
The price is NZ$351
includes taxes & fees
11 Dec - 12 Dec
Private Suite in historic Stillwater North Hill

Remarkable 3-bedroom home, indoor pool, golf, on the lake, 30 min to Twin Cities

Forest Lake
Remarkable 3-bedroom home, indoor pool, golf, on the lake, 30 min to Twin Cities

Eleanor - 2 bdr Cabin unit on River w/SUPS, Kayaks, & paddle boat. Pet friendly!

Amery
9.6 out of 10, Exceptional, (14)
"The Eleanor is a a pretty, cozy, well-appointed dwelling with a shabby-chic cottage ambience. We stayed one night, after attending a wedding at the Shed, but would have been happy to stay for a long weekend, to explore the countryside around Amery. Winter or summer, this is the perfect place for a family retreat!"
United States
Jennifer K.
The price is NZ$374
includes taxes & fees
10 Dec - 11 Dec
Eleanor - 2 bdr Cabin unit on River w/SUPS, Kayaks, & paddle boat. Pet friendly!

All seasons cabin getaway

Balsam Lake Village
10.0 out of 10, Exceptional, (53)
"Amazing cabin and host! Would love to stay again!"
United States
Malinda K.
All seasons cabin getaway

Stillwater's Third Street Inn

Stillwater
10.0 out of 10, Exceptional, (224)
"Great stay, close to downtown. Fun, clean and nice. "
United States
Anonymous traveller
Stillwater's Third Street Inn

Great Getaway Enjoy Lake Living ~ 20 minutes from St Paul and Wisconsin

St Paul
9.2 out of 10, Wonderful, (121)
"Very friendly staff"
United States
Jane
Great Getaway Enjoy Lake Living ~ 20 minutes from St Paul and Wisconsin

Beautiful Farmhouse Style Country Home with Indoor Pool!

New Richmond
10.0 out of 10, Exceptional, (55)
"This was a perfect getaway for our family, which includes three kids under 10 years old. "
United States
Holly L.
Beautiful Farmhouse Style Country Home with Indoor Pool!

Cozy Lodge Theme Home in Beautiful Hudson, WI

Hudson
9.6 out of 10, Exceptional, (79)
"Great location. Great host."
United States
Tom K.
Cozy Lodge Theme Home in Beautiful Hudson, WI

The Pine House: a cozy home for you & yours!

Stillwater
9.8 out of 10, Exceptional, (20)
"This is one of the cleanest well equipped VRBO we’ve ever stayed in. The beds were so comfortable with white duvet covers, bathrooms updated & very clean. We will definitely stay here again when in Stillwater. Thank you Haley. "
United States
Nancy O.
The Pine House: a cozy home for you & yours!

Lake Home, hot tub, sauna, boat rental, private chef

Forest Lake
10.0 out of 10, Exceptional, (63)
"Enjoyed the view and the hot tub. "
United States
Mike W.
Lake Home, hot tub, sauna, boat rental, private chef
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$156 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?

Historic Stillwater Home close to downtown: This holiday home rental outside of Osceola offers a patio, a private garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. 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.