Photo by rinchindorj

Osceola Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Osceola

Historic Beauty w Modern Updates Near Taylor's Falls
Fridge, microwave, oven, stovetop
Historic Beauty w Modern Updates Near Taylor's Falls
10.0 out of 10, Exceptional, (16)
"Great house! Close to town. Wonderful place for a family getaway."
The price is $180
$378 total
includes taxes & fees
Jun 12 - Jun 13
Historic Beauty w Modern Updates Near Taylor's Falls
Hudson Inn & Suites
Lobby
Hudson Inn & Suites
3.0 star property
8.2 out of 10, Very Good, (568)
"Spacious room, very clean, and quiet. I will most likely stay here again in my next visit to Hudson, WI."
The price is $88
$103 total
includes taxes & fees
Jun 6 - Jun 7
Hudson Inn & Suites
Hideaway From The Twin Cities: 5 Bdrms: East'n Sky, N ⭐,Sunset, Exprs, Bird Nest
Fridge, microwave, oven, stovetop
Hideaway From The Twin Cities: 5 Bdrms: East'n Sky, N ⭐,Sunset, Exprs, Bird Nest
9.4 out of 10, Exceptional, (29)
"I stayed for an extended period of time. The owner and his sons live on the property, but you won’t see them very much. The property is SO peaceful, quiet, and safe. They’ve been working to improve it and so there’s some renovations and things here and there, but nothing that would make you uncomfortable or disturb you. My kids were welcomed here, and the family even helped me through an epic flat tire crisis. They have literally everything you need and then some as far as kitchen, bathroom,...
The price is $80
$106 total
includes taxes & fees
Jun 6 - Jun 7
Hideaway From The Twin Cities: 5 Bdrms: East'n Sky, N ⭐,Sunset, Exprs, Bird Nest
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Romantic getaway! With gorgeous views from the Hot Tub!
Exterior
Romantic getaway! With gorgeous views from the Hot Tub!
9.6 out of 10, Exceptional, (74)
"This was a great location for a long girls weekend. Really nice space outdoors to enjoy and 2 comfortable beds with comfortable living space to relax in. (If you need to have adults sleep on the pull out/futon or bunk beds it may not be as comfy for bad backs ect- but the space is there if you need it) Really easy access and the long sloped sidewalk down to the unit made it easy to bring in luggage on wheels. Host was great and responsive. Just keep in mind there is no sink in the kitchenette...
The price is $75
$306 total
includes taxes & fees
Jun 6 - Jun 7
Romantic getaway! With gorgeous views from the Hot Tub!
All seasons cabin getaway
Property grounds
All seasons cabin getaway
10.0 out of 10, Exceptional, (33)
"The leaves were exploding in color during our stay at Balsam Lake. The cabin was everything we needed for a relaxing getaway. Quiet, comfortable and beautiful. We brought our canoe to explore the lake and we found some lovely wineries/breweries nearby. We would absolutely stay again!"
All seasons cabin getaway
Hideaway from the Twin Cities: 5 single rooms w/home use, 2 adult price 80/rm.
Property grounds
Hideaway from the Twin Cities: 5 single rooms w/home use, 2 adult price 80/rm.
9.6 out of 10, Exceptional, (29)
"Enjoyed our stay, just what we needed for Mother’s Day. Steve the owner was great and attentive! Thanks and we will stay again!"
The price is $80
$106 total
includes taxes & fees
Jun 6 - Jun 7
Hideaway from the Twin Cities: 5 single rooms w/home use, 2 adult price 80/rm.
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
Exterior
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
9.4 out of 10, Exceptional, (28)
"Very clean. Nice warm place to stay and close to local bars for a nice dinner. Will stay again."
The price is $105
$192 total
includes taxes & fees
Jun 10 - Jun 11
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
Log Cabin, Lake Retreat
Exterior
Log Cabin, Lake Retreat
9.6 out of 10, Exceptional, (62)
"Very cozy log cabin with everything one would need. Beautiful views and close to town for supplies. Had a great time and would definitely come back!"
Log Cabin, Lake Retreat
Gathering families, friends, & coworkers
Exterior
Gathering families, friends, & coworkers
10.0 out of 10, Exceptional, (19)
"a group of old friends stayed for a weekend to play board games and reconnect. The sanctuary was the perfect match for space and sleeping arrangements. Thanks!"
Gathering families, friends, & coworkers
Cheerful lake house close to skiing, state parks, wine tasting, and much more
Property grounds
Cheerful lake house close to skiing, state parks, wine tasting, and much more
9.4 out of 10, Exceptional, (6)
"The cabin had lots of room for sleeping, only downfall was there was not any space to play yard games."
Cheerful lake house close to skiing, state parks, wine tasting, and much more
Stillwater's Third Street Inn
Property grounds
Stillwater's Third Street Inn
10.0 out of 10, Exceptional, (187)
"We had a great stay! The house is very close to everything downtown! Everything with checking in and checking out went smooth and was very easy. It was a very clean and nice place to stay on our trip to Stillwater!"
Stillwater's Third Street Inn
River road cabin
Property grounds
River road cabin
8.8 out of 10, Excellent, (8)
"Me and some friends spent the night here during a weekend road trip. We loved the cozy interior, easy check-in and check-out process. The living room is spacious and the smart TV was a great thing to have. I would definitely recommend!"
The price is $125
$208 total
includes taxes & fees
Jun 6 - Jun 7
River road cabin
Less then 2 miles from downtown Stillwater
Fridge, microwave, oven, stovetop
Less then 2 miles from downtown Stillwater
8.4 out of 10, Very Good, (10)
"Very clean, hallway to the apartment is kind of grungy. Accommodations were well represented."
Less then 2 miles from downtown Stillwater
Nordic Harbor Haus
Property grounds
Nordic Harbor Haus
Nordic Harbor Haus
Historic Stillwater Home close to downtown
Exterior
Historic Stillwater Home close to downtown
10.0 out of 10, Exceptional, (20)
"Cozy, clean house in a great location. We enjoyed our stay!"
The price is $250
$372 total
includes taxes & fees
Jun 10 - Jun 11
Historic Stillwater Home close to downtown
Bayport's Charming Tree House
Exterior
Bayport's Charming Tree House
2.0 out of 10, (1)
The price is $247
$428 total
includes taxes & fees
Jun 7 - Jun 8
Bayport's Charming Tree House
Lakefront Cottage 2 min to downtown
Smart TV, books, stereo
Lakefront Cottage 2 min to downtown
10.0 out of 10, Exceptional, (14)
"My husband and I and my two pups booked a 4 day weekend for one last summer hurrah 9/29 through 10/2. Property was as described, location was perfect, sunrises and sunsets were beautiful. It was very peaceful as no other cabins were occupied except our host Debbie! Thank you for a wonderful get away Debbie - your property was well-maintained and lovely for our needs."
Lakefront Cottage 2 min to downtown
Cottage on the lake near downtown Stillwater
Property grounds
Cottage on the lake near downtown Stillwater
10.0 out of 10, Exceptional, (226)
"We had a fantastic stay at the cottage! The house was very clean and super comfortable for us. We made dinner and played games and enjoyed the outside one night and it was the perfect weekend! The property manager was easy to communicate with and very thorough, I had no questions or problems!"
Cottage on the lake near downtown Stillwater
Beautiful cabin getaway on Green Lake
Beautiful cabin getaway on Green Lake
10.0 out of 10, Exceptional, (128)
"My husband and I wanted to do a short get away for our 32nd wedding anniversary. Our 2 nights on Green Lake were just what we needed! Fishing, relaxing on the deck with a good book, star gazing while having a fire, it was the perfect respite from busy lives. The cabin was so comfortable, wonderful bed and very cozy. The outdoor space is so well maintained, it's really better than any other place we ever stayed, including high end resorts! They were so accommodating with dock space for our boat...
Beautiful cabin getaway on Green Lake
Overlooks St. Croix River Crossing
Aerial view
Overlooks St. Croix River Crossing
10.0 out of 10, Exceptional, (144)
"Third time here and not disappointed. Louise and Martin are great hosts. Just a short drive to downtown Stillwater and all the shops and restaurants. Will be back!"
Overlooks St. Croix River Crossing
Don't see what you're looking for?
See all available properties in Osceola
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.

Osceola Vacation Rental Travel Info

Number of vacation rentals
2
Popular accommodation
Osceola private vacation homes
Known landmarks
Dancing Dragonfly Winery, St. Croix Festival Theatre and Fawn Doe Rosa Wildlife Educational Park
International airport
Minneapolis, MN (MSP-Minneapolis - St. Paul Intl.)

Other types of properties in Osceola you may be interested in

Country Inn & Suites by Radisson, Forest Lake, MN
Exterior
Country Inn & Suites by Radisson, Forest Lake, MN
2.5 star property
8.0 out of 10, Very Good, (690)
"Nice clean room early check in"
The price is $95
$103 total
includes taxes & fees
Jun 17 - Jun 18
Country Inn & Suites by Radisson, Forest Lake, MN
Hotel Crosby
Deluxe Suite, 1 Bedroom | Individually decorated, iron/ironing board, free WiFi, bed sheets
Hotel Crosby
2.5 star property
9.4 out of 10, Exceptional, (676)
"Beautiful, super clean, and updated hotel with a fantastic bar/restaurant — fantastic cocktails! I was relaxed the moment I walked in thanks to the courteous staff (everyone was super nice), the low-lit ambience, and the cleanliness. The suite was so cozy and comfortable as well, and we enjoyed the added bonus of a balcony. Perfect for those who want to be in an unbeatable downtown Stillwater location with fantastic food and drink, great rooms, and a relaxing yet fun atmosphere. Highly...
The price is $263
$293 total
includes taxes & fees
Jun 12 - Jun 13
Hotel Crosby
Comfort Inn & Suites St. Paul Northeast
Suite, 2 Queen Beds, Non Smoking (Efficiency) | Premium bedding, desk, laptop workspace, blackout drapes
Comfort Inn & Suites St. Paul Northeast
2.5 star property
8.2 out of 10, Very Good, (1000)
"Good place to stay "
The price is $118
$128 total
includes taxes & fees
Jun 16 - Jun 17
Comfort Inn & Suites St. Paul Northeast
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.

Everything you need to know about Osceola vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osceola vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osceola vacation 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 low season months. For more hustle and bustle, you may prefer to visit Osceola in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osceola rentals

At Expedia, we put the best Osceola vacation 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 vacation.

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 vacation rental in Osceola?

Yes, you can find vacation rentals near the most popular local attractions in Osceola, or you can choose a secluded option if you're looking for relaxation. 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 vacation home rentals that Osceola has to offer?

Stillwater's Third Street Inn: This vacation home rental outside of Osceola offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Osceola?

Choose from 3 Expedia vacation rentals in Osceola for a memorable vacation.

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 vacation rentals like in Osceola?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Osceola. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.

Recent reviews of Osceola properties
Expedia verified reviews

Northwoods Best Inn -Turtle Lake

Northwoods Best Inn -Turtle Lake

5/5 Excellent
"Very welcoming"
A verified traveler stayed at Northwoods Best Inn -Turtle Lake
Posted 22 hours ago
Northwoods Best Inn -Turtle Lake