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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, (79 reviews)
"Perfect location, very clean and charming house, comfortable beds and very well stocked kitchen and home"
United States
Amy G.
The price is NZ$523
includes taxes & fees
14 June - 15 June
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 NZ$256
includes taxes & fees
17 June - 18 June
Cozy Mother-in-Law Apartment

Home on the Apple River

Home on the Apple River
Amery
10.0 out of 10, Exceptional, (5 reviews)
"Host was very helpful everythig went perfect we had a great time "
United States
Rusty S.
The price is NZ$372
includes taxes & fees
22 June - 23 June
Home on the Apple River

Lovers Lookout 1: Where Rustic Meets Luxury at Big Rock Creek

Lovers Lookout 1: Where Rustic Meets Luxury at Big Rock Creek
Saint Croix Falls
10.0 out of 10, Exceptional, (1 review)
"Everything was clean and nice when we arrived. Check in was easy by text. We were greatedby the owners not long after check in and they delivered us firewood that we purchased. Was an amazing stay and we hope to come back every year !"
United States
Jenny E.
The price is NZ$312
includes taxes & fees
15 June - 16 June
Lovers Lookout 1: Where Rustic Meets Luxury at Big Rock Creek

Hudson Inn & Suites

Hudson Inn & Suites
3.0 star property
Hudson
8.2 out of 10, Very good, (842 reviews)
"Great local hotel!"
United States
Teresa
The price is NZ$161
includes taxes & fees
22 June - 23 June
Hudson Inn & Suites

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$266
includes taxes & fees
22 June - 23 June
Lovers Lookout 2 at Big Rock Creek

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
The price is NZ$363
includes taxes & fees
22 June - 23 June
Classic Home

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
9.0 out of 10, Wonderful, (36 reviews)
"Very clear communication, comfortable beds and all the amenities you need for a night stay!"
United States
Farrah S.
The price is NZ$316
includes taxes & fees
15 June - 16 June
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park

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$302
includes taxes & fees
29 June - 30 June
The A-Frame at Big Rock Creek – A Scenic Retreat on White Oak Ridge

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.
The price is NZ$388
includes taxes & fees
22 June - 23 June
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC

Private Suite in historic Stillwater North Hill

Private Suite in historic Stillwater North Hill
Stillwater
10.0 out of 10, Exceptional, (37 reviews)
"This was the perfect spot for a couple nights in Stillwater. Comfortable bed. Cute decorations. Very clean. The host was very responsive. We hope to stay again when we return for a weekend getaway."
United States
Ronda
The price is NZ$481
includes taxes & fees
15 June - 16 June
Private Suite in historic Stillwater North Hill

Scandinavian Retreat

Scandinavian Retreat
Taylors Falls
10.0 out of 10, Exceptional, (39 reviews)
"Beautiful place, great location and amazing hosts!!!!"
United States
Dylan M.
The price is NZ$692
includes taxes & fees
15 June - 16 June
Scandinavian Retreat

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$656
includes taxes & fees
28 June - 29 June
BestLocation|Romantic|ViewBridgeFromBed|Couples|Pets|Photo backdrop|Nightlife!!!

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 NZ$563
includes taxes & fees
24 June - 25 June
Lake Home property

Minne-GetAway: Modern Cottage

Minne-GetAway: Modern Cottage
North Saint Paul
9.6 out of 10, Exceptional, (15 reviews)
"Comfortable beds and clean bathrooms."
United States
Angelika
The price is NZ$476
includes taxes & fees
30 June - 1 July
Minne-GetAway: Modern Cottage

Relaxing Townhouse Escape

Relaxing Townhouse Escape
Hugo
9.0 out of 10, Wonderful, (19 reviews)
"Clean & comfortable stay. Great location and appreciated use of the garage for additional parking space. "
United States
Jennifer L.
The price is NZ$494
includes taxes & fees
12 July - 13 July
Relaxing Townhouse Escape

Historic Stillwater Home close to downtown

Historic Stillwater Home close to downtown
Stillwater
10.0 out of 10, Exceptional, (74 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$630
includes taxes & fees
5 July - 6 July
Historic Stillwater Home close to downtown

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.
The price is NZ$590
includes taxes & fees
16 June - 17 June
Peaceful 3-bedroom cabin in charming Amery
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$161 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?

Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park : This holiday home rental outside of Osceola is located on a lake, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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?

Saint Croix River and Apple 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.