Osceola Vacation Rentals

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Nov 23 - Nov 24
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Vacation Rentals in Osceola

Outdoor dining
Historic 1880s Home

Vacation Home in 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.
$205 nightly
The price is $227
Nov 24 - Nov 25
Total with taxes and fees
Historic 1880s Home
Lobby
Hudson Inn & Suites

Aparthotel in Hudson

3.0 star property
8.2 out of 10, Very Good, (807)
"Nice property offering a descent stay at "
United States
Kimberly
$85 nightly
The price is $92
Nov 26 - Nov 27
Total with taxes and fees
Hudson Inn & Suites
Exterior
Gathering families, friends, & coworkers

Vacation Home in Clear Lake

9.8 out of 10, Exceptional, (37)
"Bobbi was wonderful throughout our time there at the Sanctuary. We had 46 people staying there for our family reunion and it was amazing! The kitchen was fully stocked. We had 2 large gathering places and the beds were comfortable. Checkout was smooth too. We liked it so much that we will be going back for our next family reunion."
United States
Tim G.
Gathering families, friends, & coworkers
Property grounds
Lakefront, Hot Tub, Golf, Kayaks, ATV, Snowmobile Trails, St.Croix Casino

Cabin in Turtle Lake

10.0 out of 10, Exceptional, (15)
"Great place to stay and in quiet setting! "
United States
Steve G.
$634 nightly
The price is $695
Nov 24 - Nov 25
Total with taxes and fees
Lakefront, Hot Tub, Golf, Kayaks, ATV, Snowmobile Trails, St.Croix Casino
Outdoor spa tub
Luxe Lakefront Estate near Minneapolis, Hot Tub, Sauna, Kayaks, Sleeps up to 20

Vacation Home in 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
Exterior
Romantic getaway! With gorgeous views from the Hot Tub!

Apartment in 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.
$246 nightly
The price is $264
Nov 24 - Nov 25
Total with taxes and fees
Romantic getaway! With gorgeous views from the Hot Tub!
Property grounds
Stillwater's Third Street Inn

Vacation Home in Stillwater

10.0 out of 10, Exceptional, (223)
"Great stay, close to downtown. Fun, clean and nice. "
United States
Anonymous traveler
Stillwater's Third Street Inn
Indoor pool, a heated pool
Remarkable 3-bedroom home, indoor pool, golf, on the lake, 30 min to Twin Cities

Vacation Home in Forest Lake

Remarkable 3-bedroom home, indoor pool, golf, on the lake, 30 min to Twin Cities
Exterior
Historic Stillwater Home close to downtown

Vacation Home in Stillwater

10.0 out of 10, Exceptional, (59)
"Beautiful property with great touches throughout! Very welcoming and comfortable for our stay! Would definitely stay here again the next time I am visiting Stillwater!"
United States
Michelle B.
$310 nightly
The price is $338
Nov 24 - Nov 25
Total with taxes and fees
Historic Stillwater Home close to downtown
Exterior
Historic Swedish Cottage on Quiet Lindstrom Lake

Vacation Home in Lindstrom

9.4 out of 10, Exceptional, (231)
"Wonderful for our gathering! Very comfortable!"
United States
Mike and Grayce G.
$686 nightly
The price is $737
Nov 24 - Nov 25
Total with taxes and fees
Historic Swedish Cottage on Quiet Lindstrom Lake
Indoor pool
Beautiful Farmhouse Style Country Home with Indoor Pool!

Vacation Home in New Richmond

10.0 out of 10, Exceptional, (55)
"Easy check-in, wonderful host with great communication and really nice pool. Very relaxing property. Had everything we needed. Would definitely stay here again! "
United States
Jen S.
Beautiful Farmhouse Style Country Home with Indoor Pool!
Outdoor dining
Historic James Mulvey Carriage house (Whole house)

Cottage in Stillwater

9.8 out of 10, Exceptional, (33)
"Wonderful stay. Loved the pool!"
United States
Wendy H.
$726 nightly
The price is $807
Nov 25 - Nov 26
Total with taxes and fees
Historic James Mulvey Carriage house (Whole house)
Great Getaway Enjoy Lake Living ~ 20 minutes from St Paul and Wisconsin

Vacation Home in 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
Stovetop, dishwasher, paper towels
Cozy 5-Star Guesthouse on Bald Eagle Lake - Serene and Peaceful.

Vacation Home in Hugo

9.8 out of 10, Exceptional, (8)
"Excellent host, excellent location. "
United States
Julio E.
$225 nightly
The price is $244
Nov 25 - Nov 26
Total with taxes and fees
Cozy 5-Star Guesthouse on Bald Eagle Lake - Serene and Peaceful.
Exterior
Park Place Cottage

Cottage in Mahtomedi

9.6 out of 10, Exceptional, (37)
"Good place. cozy and comfortable"
United States
Jesse L.
Park Place Cottage
Miscellaneous
St. Croix Riverview Home...Walking Distance to Downtown Stillwater

Vacation Home in Stillwater

9.8 out of 10, Exceptional, (146)
"Beautiful home, fantastic location- great proximity to downtown Stillwater- lots to do and see. The hosts were very nice, respectful and responsive. We highly recommend!"
United States
P D.
St. Croix Riverview Home...Walking Distance to Downtown Stillwater
Property grounds
Spacious 4-bedroom house with private access to river in Willow River State Park

Vacation Home in Hudson

10.0 out of 10, Exceptional, (9)
"We enjoyed our stay. The house was so peaceful and relaxing. We would definitely stay again. "
United States
Jennifer A.
Spacious 4-bedroom house with private access to river in Willow River State Park
Interior
Private Suite in historic Stillwater North Hill

Apartment in Stillwater

10.0 out of 10, Exceptional, (29)
"The hosts and place were fantastic all around! "
United States
Tabitha B.
$220 nightly
The price is $240
Dec 1 - Dec 2
Total with taxes and fees
Private Suite in historic Stillwater North Hill
Exterior
Log Cabin, Lake Retreat

Cabin in New Richmond

9.8 out of 10, Exceptional, (89)
"It was a perfect cabin and location for a long weekend getaway! Beautiful view of the lake and plenty of space for a group. "
United States
Randi K.
Log Cabin, Lake Retreat
Terrace/patio
Lumberjack Inn 2300 sq.ft in DT with a rooftop

Apartment in Stillwater

9.6 out of 10, Exceptional, (40)
"We loved our stay at the Lumberjack! Everything was great, clean, and the rooftop space and view were so amazing, especially in the morning before exploring Stillwater or in the evening!!! Definitely would stay here again!Vicki"
United States
Vicki O.
Lumberjack Inn 2300 sq.ft in DT with a rooftop
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

Water Street Inn

Water Street Inn

10/10 Excellent
"Cozy room, great view"
Emily 1-night trip
Posted 2 days ago
Water Street Inn

Find out more about Osceola

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 $92 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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Osceola?

Yes, you can find vacation rentals in Osceola near Osceola & St. Croix Valley Railway, or you can go with a secluded option if you're looking for extra privacy while you relax. 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?

Historic Stillwater Home close to downtown: This vacation home rental outside of Osceola offers a patio, a private yard, 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 the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Osceola?

Choose from 6 Expedia vacation rentals in Osceola for a memorable vacation.

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 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.