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Search Holiday Rentals in Osceola

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Top Holiday Rentals in Osceola

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 £289
per night
5 May - 6 May
Historic Beauty w Modern Updates Near Taylor's Falls
Lobby
Hudson Inn & Suites
3.0 star property
8.2 out of 10, Very good, (549)
"Very well kept and maintained. Have stayed here many times."
The price is £82
per night
5 May - 6 May
Hudson Inn & Suites
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, (28)
"Such a beautiful home and property. Read the description before you book, but Steve was great!!! The fresh fruit, coffee, and cinnamon rolls were an extra treat. I would stay again for sure!"
The price is £87
per night
7 May - 8 May
Hideaway From The Twin Cities: 5 Bdrms: East'n Sky, N ⭐,Sunset, Exprs, Bird Nest
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Property grounds
Romantic getaway! With gorgeous views from the Hot Tub!
9.6 out of 10, Exceptional, (71)
"It was very well kept, nice quiet getaway."
The price is £250
per night
16 May - 17 May
Romantic getaway! With gorgeous views from the Hot Tub!
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 £156
per night
14 May - 15 May
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
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
Property grounds
Stillwater's Third Street Inn
10.0 out of 10, Exceptional, (186)
"Everything was great with the property. Great place, great location, easy check in, great communications with the property owner. We will definitely look to book again when we return to Stillwater."
Stillwater's Third Street Inn
Property grounds
Hideaway from the Twin Cities: 5 single rooms w/home use, 2 adult price 80/rm.
9.6 out of 10, Exceptional, (28)
"The house was large and comfortable. Breakfast was prepared with freah fruits and cinnamon rolls. It was a very welcoming stay."
The price is £87
per night
4 May - 5 May
Hideaway from the Twin Cities: 5 single rooms w/home use, 2 adult price 80/rm.
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
Exterior
Blocks to Downtown. Charming 3 Bed, Entire House
10.0 out of 10, Exceptional, (45)
"Very roomy and comfortable home. Excellent location. No issues with the property. We enjoyed our stay and would visit again."
Blocks to Downtown. Charming 3 Bed, Entire House
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
Indoor pool
Beautiful Farmhouse Style Country Home with Indoor Pool!
10.0 out of 10, Exceptional, (17)
"This place was perfect! Great for a girls weekend! Was full stocked and very comfortable!"
Beautiful Farmhouse Style Country Home with Indoor Pool!
Property grounds
Nordic Harbor Haus
Nordic Harbor Haus
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
Property grounds
River road cabin
8.6 out of 10, Excellent, (7)
"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 £162
per night
6 May - 7 May
River road cabin
TV
MainStreetLocation|GirlsNight|Families|Pets|FoodMusicShopArtExploreBikeFunPlay!!
9.4 out of 10, Exceptional, (79)
"Cozy environment, with everything you need. Great location in the center of downtown. Close to shops, restaurants, and wine bars. Check-in was very easy and there was immediate response when anything was needed."
MainStreetLocation|GirlsNight|Families|Pets|FoodMusicShopArtExploreBikeFunPlay!!
Aerial view
Overlooks St. Croix River Crossing
10.0 out of 10, Exceptional, (142)
"We spent two weeks at this adorable cottage, it was decorated so cute and the comforts and the conveniences were great. Location was idea for us to walk, check out the historic downtown, and spend time with our family. Thank you Louise and Martin, we enjoyed our stay, was hard to leave!"
Overlooks St. Croix River Crossing
Beautiful cabin getaway on Green Lake
10.0 out of 10, Exceptional, (126)
"My home had an electrical fire. This stay was beautiful and gave me the perfect atmosphere to heal from my losses from the fire. Things are a lot better now."
Beautiful cabin getaway on Green Lake
Property grounds
Cottage on the lake near downtown Stillwater
10.0 out of 10, Exceptional, (225)
"It was a wonderful experience, the house was an accurate listing, clean and when we had a small issue with a beeping noise in the house on arrival the host was prompt in replies. Came very quickly and was extremely friendly dealing with it! Would definitely stay here again!"
Cottage on the lake near downtown Stillwater
Interior
The Lake Hideaway, 2 bdrm in heart of downtown WBL
10.0 out of 10, Exceptional, (15)
"Had a very good experience and enjoyed our stay"
The price is £314
per night
7 May - 8 May
The Lake Hideaway, 2 bdrm in heart of downtown WBL
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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 Holiday Rental Travel Info

Other types of properties in Osceola you may be interested in

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, (662)
"Such a beautiful place to stay in downtown Stillwater! "
The price is £239
per night
5 May - 6 May
Hotel Crosby
Suite, 2 Queen Beds, Non Smoking (Efficiency) | Premium bedding, desk, laptop workspace, blackout curtains
Comfort Inn & Suites St. Paul Northeast
2.5 star property
8.2 out of 10, Very good, (1000)
" Nice hotel - much better than I expected.clean room,friendly staff, pool area was nice also."
The price is £85
per night
26 May - 27 May
Comfort Inn & Suites St. Paul Northeast
Exterior
Best Western Plus White Bear Country Inn
3.0 star property
8.8 out of 10, Excellent, (1002)
"Great breakfasts & coffee!"
The price is £99
per night
19 May - 20 May
Best Western Plus White Bear Country Inn
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 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, apart-hotels, 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 £82 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 close to the most popular sights in Osceola, 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?

Hideaway From The Twin Cities: 5 Bdrms: East'n Sky, N ⭐,Sunset, Exprs, Bird Nest: This holiday home rental outside of Osceola is located in a rural location, and has a patio, a BBQ and air conditioning to put you at ease 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.

How many holiday rentals are there in Osceola?

Choose from 3 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.

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