Osceola Holiday Rentals

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Our top choices for Osceola holiday rentals

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 AU$370
includes taxes & fees
27 May - 28 May
Historic 1880s Home

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 AU$209
includes taxes & fees
21 May - 22 May
Cozy Mother-in-Law Apartment

Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very good, (829 reviews)
"Nice place, good location."
United States
john
The price is AU$125
includes taxes & fees
2 June - 3 June
Hudson Inn & Suites

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.
The price is AU$601
includes taxes & fees
24 May - 25 May
Private 3bdr cabin on Apple River kayaks, SUPS, & Sauna. Pet friendly!

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 AU$474
includes taxes & fees
17 May - 18 May
Historic Stillwater Home close to downtown

Historic Swedish Cottage on Quiet Lindstrom Lake

Historic Swedish Cottage on Quiet Lindstrom Lake
Lindstrom
9.4 out of 10, Exceptional, (239 reviews)
"Great stay, beautiful views, comfortable. and clean."
United States
CHRISTOPHER
The price is AU$991
includes taxes & fees
28 May - 29 May
Historic Swedish Cottage on Quiet Lindstrom Lake

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.
Escape to The Clubhouse at Big Rock Creek – Your All-Season Adventure Awaits!

Luxurious remodel near historic downtown Hudson!

Luxurious remodel near historic downtown Hudson!
Hudson
10.0 out of 10, Exceptional, (31 reviews)
"Perfect for a girls get away! "
United States
Anne D.
The price is AU$661
includes taxes & fees
17 May - 18 May
Luxurious remodel near historic downtown Hudson!

Nordic Harbor | Room 5 | Cedar Shadows

Nordic Harbor | Room 5 | Cedar Shadows
Center City
9.8 out of 10, Exceptional, (8 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.
The price is AU$427
includes taxes & fees
17 May - 18 May
Nordic Harbor | Room 5 | Cedar Shadows

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 AU$309
includes taxes & fees
7 June - 8 June
Home on the Apple River

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 AU$270
includes taxes & fees
19 May - 20 May
1 Bdr Cabin duplex unit on Apple River. Kayaks, SUPs & Sauna. Pet friendly!

Gorgeous 5 bed Remodel near Downtown Hudson for Groups!

Gorgeous 5 bed Remodel near Downtown Hudson for Groups!
Hudson
10.0 out of 10, Exceptional, (11 reviews)
"This home was an excellent place to stay. The beds were super comfortable and everything in the home was very clean. We would definitely stay here again. Great communication with the host."
United States
Elizabeth F.
The price is AU$1,499
includes taxes & fees
17 May - 18 May
Gorgeous 5 bed Remodel near Downtown Hudson for Groups!

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 AU$300
includes taxes & fees
27 May - 28 May
Classic Home

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 AU$498
includes taxes & fees
18 May - 19 May
Scandinavian Retreat

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 AU$828
includes taxes & fees
17 May - 18 May
Midcentury Lake Home!

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.
The price is AU$619
includes taxes & fees
18 May - 19 May
Nordic Harbor | Room 3 | Arctic Pine - Suite

Woodsy Retreat: Chef's Kitchen, Dance Room & Gym

Woodsy Retreat: Chef's Kitchen, Dance Room & Gym
White Bear Lake
9.6 out of 10, Exceptional, (8 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 AU$486
includes taxes & fees
18 May - 19 May
Woodsy Retreat: Chef's Kitchen, Dance Room & Gym

CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails

CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails
Stillwater
9.8 out of 10, Exceptional, (7 reviews)
"Excellent place to stay. We will definitely be returning. Host was very accommodating."
United States
Judy K.
The price is AU$948
includes taxes & fees
17 May - 18 May
CHARMING RETREAT! Over-looking Lake, Hot tub, WiFi, AC, Nearby Walking Trails

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 AU$386
includes taxes & fees
19 May - 20 May
Lake Home property

MainStreetLocation|GirlsNight|Families|Pets|FoodMusicShopArtExploreBikeFunPlay!!

MainStreetLocation|GirlsNight|Families|Pets|FoodMusicShopArtExploreBikeFunPlay!!
Stillwater
9.4 out of 10, Exceptional, (101 reviews)
"Great location for girls' weekend"
United States
Diane H.
The price is AU$537
includes taxes & fees
17 May - 18 May
MainStreetLocation|GirlsNight|Families|Pets|FoodMusicShopArtExploreBikeFunPlay!!
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 favourite 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 depend 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 AU$125 per night. Entering your travel dates in the search wizard might find you 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?

Get away from it all and relax on the lake!: This holiday home rental outside of Osceola is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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.