Osceola Holiday Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Osceola holiday rentals

Exterior

Apartment in Osceola

Cozy Mother-in-Law Apartment
10.0 out of 10, Exceptional, (51 reviews)
"Wonderful stay. So many great features and very clean. Would definitely stay again!"
United States
Nicole A.
The price is HK$767
HK$1,021 total
includes taxes & fees
3 Mar - 4 Mar
Cozy Mother-in-Law Apartment
Interior

Holiday Home in Osceola

Historic 1880s Home
10.0 out of 10, Exceptional, (73 reviews)
"This is a beautiful home very close to downtown and restaurants. The host did an amazing job! We would love to stay here again! "
United States
Kristine R.
The price is HK$1,401
HK$1,765 total
includes taxes & fees
3 Mar - 4 Mar
Historic 1880s Home
Dining

Cabin in Amery

Eleanor - 2 bdr Cabin unit on River w/SUPS, Kayaks, & paddle boat. Pet friendly!
9.6 out of 10, Exceptional, (15 reviews)
"The Eleanor was very clean, relaxing and had everything we needed. We enjoyed our stay and the grounds had kayaks for us to get out on the lake. We definitely recommend staying here."
United States
Jayme W.
The price is HK$1,021
HK$1,690 total
includes taxes & fees
3 Mar - 4 Mar
Eleanor - 2 bdr Cabin unit on River w/SUPS, Kayaks, & paddle boat. Pet friendly!
Dining

Cabin in Amery

1 Bdr Cabin unit Respite on Apple River. Kayaks, SUPs, and more! Pet friendly!
9.8 out of 10, Exceptional, (16 reviews)
"It’s was clean and modern. We enjoyed our stay "
United States
Derek K.
The price is HK$845
HK$1,418 total
includes taxes & fees
3 Mar - 4 Mar
1 Bdr Cabin unit Respite on Apple River. Kayaks, SUPs, and more! Pet friendly!
Exterior

Apartment in Taylors Falls

Romantic getaway! With gorgeous views from the Hot Tub!
9.4 out of 10, Exceptional, (105 reviews)
"Great value! I would stay again."
United States
Matt C.
The price is HK$587
HK$2,134 total
includes taxes & fees
3 Mar - 4 Mar
Romantic getaway! With gorgeous views from the Hot Tub!
Desk, iron/ironing board, free WiFi, bed sheets

Aparthotel in Hudson

Hudson Inn & Suites
3.0 star property
8.2 out of 10, Very good, (816 reviews)
"It was clean and staff persons were polite and professional."
United States
Michael
The price is HK$553
HK$660 total
includes taxes & fees
4 Mar - 5 Mar
Hudson Inn & Suites
Exterior

Cabin in Luck

Lake Home property
9.6 out of 10, Exceptional, (13 reviews)
"The place is more of a home than a cabin. Simply beautiful, cozy and comfortable "
United States
Cathy
Lake Home property
Exterior

Holiday Home in Balsam Lake Village

Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
9.2 out of 10, Wonderful, (35 reviews)
"Lovely, cozy house. We enjoyed our stay!"
United States
Geoff P.
The price is HK$775
HK$1,453 total
includes taxes & fees
3 Mar - 4 Mar
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
WiFi, bed sheets

Cabin in Taylors Falls

Wannigan Point Cabin #4
10.0 out of 10, Exceptional, (2 reviews)
"This was a great location and a lovely cabin. However, when we used the oven there was a strong smell. Other than that, we had a wonderful time. Thank you."
United States
michelle b.
The price is HK$1,095
HK$2,058 total
includes taxes & fees
13 Mar - 14 Mar
Wannigan Point Cabin #4
Smart TV

Holiday Home in Taylors Falls

Scandinavian Retreat
10.0 out of 10, Exceptional, (36 reviews)
"The property was so clean and beautifully decorated. Thoughtful hosts and lovely community. "
United States
Hollie A.
The price is HK$1,296
HK$2,820 total
includes taxes & fees
4 Mar - 5 Mar
Scandinavian Retreat
Interior

Holiday Home in White Bear Lake

Woodsy Retreat: Chef's Kitchen, Dance Room & Gym
10.0 out of 10, Exceptional, (7 reviews)
"The house was great. Clean. Loved the bathroom. Everything we needed for our stay and more"
United States
Rhoda O.
The price is HK$845
HK$2,679 total
includes taxes & fees
3 Mar - 4 Mar
Woodsy Retreat: Chef's Kitchen, Dance Room & Gym
Smart TV

Holiday Home in North Saint Paul

Minne-GetAway: Modern Cottage
9.6 out of 10, Exceptional, (14 reviews)
"Comfortable beds and clean bathrooms."
United States
Angelika
The price is HK$676
HK$2,055 total
includes taxes & fees
3 Mar - 4 Mar
Minne-GetAway: Modern Cottage
Terrace/patio

Apartment in Stillwater

Private Suite in historic Stillwater North Hill
10.0 out of 10, Exceptional, (33 reviews)
"The hosts and place were fantastic all around! "
United States
Tabitha B.
The price is HK$861
HK$1,780 total
includes taxes & fees
3 Mar - 4 Mar
Private Suite in historic Stillwater North Hill
Exterior detail

Apartment in Somerset

Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC
9.8 out of 10, Exceptional, (9 reviews)
"Very clean and exactly as described, would stay again! "
United States
Thomas R.
The price is HK$1,232
HK$1,785 total
includes taxes & fees
3 Mar - 4 Mar
Lower unit of a two-story duplex w/two bedrooms in Somerset with WiFi, AC
1 bedroom, WiFi, bed sheets

Holiday Home in Center City

Nordic Harbor | Room 1 | Acorn Oak
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 HK$1,878
HK$2,398 total
includes taxes & fees
3 Mar - 4 Mar
Nordic Harbor | Room 1 | Acorn Oak
Exterior

Holiday Home in Stillwater

Historic Stillwater Home close to downtown
10.0 out of 10, Exceptional, (67 reviews)
"Very walkable distance from downtown. We loved our stay and appreciated all the sweet touches and amenities!"
United States
Allyssa M.
The price is HK$1,760
HK$2,666 total
includes taxes & fees
5 Mar - 6 Mar
Historic Stillwater Home close to downtown
Exterior

Cabin in Saint Croix Falls

River road cabin
8.0 out of 10, Very good, (14 reviews)
"Great stay. Would do it again."
United States
Jeff W.
The price is HK$775
HK$1,411 total
includes taxes & fees
3 Mar - 4 Mar
River road cabin
Exterior

Cabin in Saint Croix Falls

Where Comfort Meets Adventure — In Every Season!
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 HK$853
HK$1,948 total
includes taxes & fees
5 Mar - 6 Mar
Where Comfort Meets Adventure — In Every Season!
Smart TV

Apartment in Stillwater

BestLocation|Romantic|ViewBridgeFromBed|Couples|Pets|Photo backdrop|Nightlife!!!
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 HK$1,471
HK$2,964 total
includes taxes & fees
4 Mar - 5 Mar
BestLocation|Romantic|ViewBridgeFromBed|Couples|Pets|Photo backdrop|Nightlife!!!
Living area

Mobile Home in Amery

Home on the Apple River
10.0 out of 10, Exceptional, (4 reviews)
"Great location right on the river. A beautiful view and nice property. Very close to Amery to get supplies and visit nice shopping options. Very comfortable accommodation. Owner was very responsive to any questions. A great value and overall experience. "
United States
Jason D.
The price is HK$900
HK$1,609 total
includes taxes & fees
4 Mar - 5 Mar
Home on the Apple River
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

Best Western Plus White Bear Country Inn

Best Western Plus White Bear Country Inn

10/10 Excellent
"Outstanding accommodations, gracious staff"
Donald 1-night trip
Posted 4 days ago
Best Western Plus White Bear Country Inn

Find out more about Osceola

Search for holiday rentals in Osceola on Expedia! You can easily find your home rentals, villas, holiday apartments in Osceola using one of the methods below:

  • View our selection of featured holiday rentals in Osceola
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  • Enter your travel dates to view the best deals on holiday rentals in Osceola while they last

Look no further and take a look at our great range of rental properties in Osceola!

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.