Osceola Vacation Rentals, Wisconsin: house rentals & more

Discover a selection of vacation rentals in Osceola that are perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include air conditioning and a pool. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Historic Beauty w Modern Updates Near Taylor's Falls

Sleeps 11 · 4 bedrooms · 1 bathroom

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Find out more about Osceola

Why visit Osceola

Outdoor Adventures: Enjoy hiking, biking, and exploring scenic trails in nearby state and national parks.
Serene St. Croix River: Relax by the river, perfect for fishing, kayaking, and enjoying nature.
Charming Local Beaches: Unwind at beautiful beaches ideal for picnics and sunbathing.
Family-Friendly Atmosphere: Experience Osceola's welcoming community and activities for all ages.
Cozy Accommodations: Choose from a variety of vacation rentals, including cabins and apartments.

Popular types of accommodation in Osceola

Discover the charm of Osceola with our diverse vacation rentals, including houses, cozy cabins, and modern apartments. Whether you're looking to rent in Osceola for a family getaway or seeking a suite in Osceola Place, we have options to suit every budget. For those searching for affordable lodging, check out our selection of cheap apartments. Your perfect Osceola escape awaits!

Houses: The top choice for visitors in Osceola, offering spacious accommodations ideal for families or groups.
Apartments: A popular option for travelers seeking a convenient and comfortable stay in the heart of the town.
Cabins: A charming and rustic lodging choice, perfect for those wanting to immerse themselves in nature.
Cottages: Cozy and inviting, these rentals provide a homey feel for a relaxing getaway.
Condos: Great for those looking for modern amenities and a central location during their stay.**

Top attractions in Osceola

Osceola, Wisconsin, is a charming destination perfect for outdoor enthusiasts and those seeking scenic beauty and romance. Visitors can explore nearby national and state parks, enjoy the rivers, and relax at local beaches. Whether you're looking for adventure or a peaceful retreat, Osceola offers a variety of attractions that cater to all types of travelers, making it an ideal spot for a memorable vacation.

Osceola & St. Croix Valley Railway: Experience a charming ride on this historic railway, where you can enjoy scenic views of the St. Croix Valley while immersing yourself in the area's rich culture and heritage.
Saint Croix River: This picturesque river, located a short drive from Osceola, offers stunning scenery and a variety of outdoor activities such as fishing, canoeing, and hiking along its peaceful banks.
Interstate State Park: Just 5 miles away, this national park is a haven for adventure seekers, featuring breathtaking landscapes, hiking trails, and opportunities for rock climbing and camping.

Things to do recommended for couples

For a romantic getaway in Osceola, enjoy skiing at Trollhaugen, just 5 miles away, for some snowy fun. Catch a live show at the Somerset Amphitheater, located 13 miles from town, or embark on an adventurous canoe trip with Riverwood Canoe right in Osceola.

Things to do recommended for families

Families can explore the serene St. Croix National Scenic Riverway, just 7 miles from Osceola, offering wellness and relaxation. Additionally, the St. Croix Islands State Recreation Area, located 17 miles away, provides a tranquil setting for outdoor fun and family bonding.

Things to do recommended for groups

Groups visiting Osceola can enjoy a captivating performance at the St. Croix Festival Theatre, hit the greens at the St. Croix Valley Golf Course, or try their luck at the Running Aces Casino for an exciting night out, all within a short drive.

What do I need to keep in mind when booking a vacation in Osceola

When planning your trip—whether you're traveling with friends, family, pets, or seeking extended stays—be sure to prioritize your preferences in your search. Here are some helpful Vrbo booking tips to assist you.

Traveling to Osceola with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group activities. Luckily, you can easily filter for all of these options and more on Vrbo.
Traveling to Osceola with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, you should think about how close you are to family-friendly attractions.
Taking your pets with you to Osceola: For many families, a vacation wouldn’t feel complete without their furry companion. If you can relate, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
Planning for a long term stay visiting Osceola: If you're in search of vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Osceola

Osceola, Wisconsin, offers a delightful blend of outdoor adventures and romantic scenery, perfect for a relaxing getaway. With friendly locals and a family-friendly atmosphere, you can explore charming parks, scenic trails, and the serene St. Croix River. Neighboring towns like Stillwater and Taylors Falls provide additional excursions and unique experiences. Whether you’re seeking tranquility or fun-filled outings, Osceola is an ideal destination for creating lasting memories.

Balsam Lake: Located 15 miles from Osceola, Balsam Lake is a charming city that captivates visitors with its stunning natural scenery. Known for its inviting outdoor spaces, this locale is perfect for romance and relaxation. The nearby recreational area offers activities such as skiing in the winter and hiking in the warmer months. The local lake and national state park provide breathtaking views and opportunities for fishing, boating, and picnicking. Balsam Lake is a true escape for nature lovers seeking tranquility and adventure.
Stillwater: Situated 19 miles from Osceola, Stillwater exudes a family-friendly atmosphere combined with romantic charm. This picturesque city is perfect for outdoor enthusiasts, offering a plethora of recreational activities. Stroll through the scenic parks, explore the nearby national state park, or enjoy a leisurely day at the lake. Stillwater's shopping mall and various boutique shops make it a vibrant destination for shoppers. With its rich history and beautiful riverfront, Stillwater promises a delightful blend of exploration and relaxation for visitors of all ages.
Taylors Falls: Just 6 miles from Osceola, Taylors Falls is a haven for adventure seekers and nature enthusiasts. Nestled along the St. Croix River, this city offers breathtaking views and a wealth of outdoor activities. Visitors can explore the recreational area, which includes ski fields for winter fun and numerous trails for hiking and biking. The surrounding national state park features stunning rock formations and scenic overlooks, perfect for capturing memorable photos. Taylors Falls is a must-visit for those seeking both adventure and natural beauty.

Booking with Vrbo is simple

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay, which can lead to substantial savings. To discover a Vrbo property that meets your budget, utilize our filters to sort by price, location, and type of vacation rental. We’re here to help you find the perfect place for your getaway!

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash™ on the full booking amount. It’s a great advantage to be the planner! Become a part of our One Key rewards program to unlock exclusive savings available only to members and accumulate OneKeyCash™ on eligible stays. Sign up today and begin earning!

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers an easy-to-use platform where you can plan new trips, continue from where you last stopped, and manage your travel arrangements. You'll see your saved or booked properties neatly organized under categories like Potential, Upcoming, or Current Trips. To begin making the most of Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Head to the tranquil city of Osceola

Enjoy the entertainment and other features of Osceola. Travelers like the riverfront, bars and waterfalls in this relaxing and welcoming city. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Osceola

Are you hoping to discover things to do while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Osceola a one-of-a-kind vacation spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

Trollhaugen (4.6 mi / 7.4 km)
Fawn Doe Rosa Wildlife Educational Park (7.5 mi / 12 km)
Dancing Dragonfly Winery (7.7 mi / 12.4 km)
WineHaven Winery and Vineyard (10.5 mi / 16.9 km)
Wild Mountain (11.7 mi / 18.8 km)
Wild Mountain Winery (12.6 mi / 20.3 km)

Exploring the natural features in Osceola

Whether you're an active traveler or just want to appreciate the scenery, Osceola is a great place to get out in nature. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

Franconia Sculpture Park (4.2 mi / 6.8 km)
Saint Croix River (6.8 mi / 10.9 km)
St Croix National Scenic Riverway (7.2 mi / 11.6 km)
Fawn Doe Rosa Wildlife Educational Park (7.5 mi / 12 km)
Interstate State Park- Wisconsin (9.5 mi / 15.2 km)
Big Marine Lake (10.3 mi / 16.5 km)

How to get to and around Osceola

The nearest airport is in St. Paul, MN (STP-St. Paul Downtown), located 32.1 mi (51.7 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Minneapolis - St. Paul Intl. Airport (MSP), which is 39 mi (62.8 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Osceola?

The most in-demand types of vacation rentals in Osceola are apartments. After something a little different? Vrbo has numerous options to match the unique needs of our guests, so you’ll see properties in all sizes, and for all budgets. The ideal fit is waiting for you — lock in yours today.

How much does it cost to rent a vacation rental in Osceola?

Season, property type and length of stay are some of the things that can influence the price of a vacation home. Simply add your travel dates to find your perfect match. From comfy cabins to expansive villas, all Vrbo vacation rentals provide unbeatable value.

How much does it cost to rent a beach house in Osceola?

Prices for beach houses in Osceola will vary depending on the size and style of the property and time of year you’re traveling. Just enter your travel dates into Vrbo and the number of guests to view vacation rental options and prices. From there you can use our filter tool to refine your search by ratings, amenities, nearby activities and more.

Are there pet-friendly vacation rentals in Osceola?

Yes, there are. You can pick from 10 vacation rentals that allow pets in Osceola. Some of our pet-friendly vacation rentals even have a garden for your four-legged fur baby to play around in, dog beds, complimentary treats and proximity to parks and green space. Apply the “Pets allowed” filter to find a pad that’ll set tails wagging on Vrbo.

What are popular rental amenities in Osceola?

A firepit, a fireplace and tennis top the list of most popular rental amenities in Osceola. Whether you’re taking to the road on your own, with your significant other or a group of friends, Vrbo can help you find a vacation home that matches your tastes with all the features you’ll enjoy.

Are there large group vacation rentals in Osceola?

With two vacation rentals that can sleep 10 or more guests in Osceola, you won’t have to keep your invite list short. From family vacations to events like birthday and Christmas parties, Vrbo will help you find a large group rental to match the occasion.

Are there vacation rentals in Osceola that welcome kids?

Bring the entire group together for an unforgettable adventure in Osceola at one of our 10 family-friendly vacation rentals. Many of these stays provide amenities that are perfect for getaways with youngsters, such as kitchens, multiple bedrooms and patios. Just click on the “Properties good for families” filter and pick your favorite option.

What are the top attractions for families in Osceola?

If you’re traveling with the kids, be sure to put these family-friendly attractions in Osceola on your to-do list:

Osceola & St. Croix Valley Railway
Riverwood Canoe

Can I find two-bedroom vacation rentals in Osceola?

Gather your family and experience complete comfort and privacy in one of the three two-bedroom vacation homes Osceola has to offer.

Are there vacation rentals with WiFi in Osceola?

Osceola has six vacation rentals with WiFi, so you’ll be able to stay connected while traveling. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming movie blockbusters to posting pics on social media, these Vrbo homes make it a cinch to go online.

How can I find vacation rentals with air conditioning in Osceola?

Osceola has nine vacation rentals where you can relax in air-conditioned comfort. To book a property on Vrbo that has this perk, enter your travel dates and use the filters to select the “air conditioning” box.

How old do you have to be to rent a vacation rental in Osceola?

The minimum age permitted can vary across properties on Vrbo, so be sure to check the rules of the vacation rental in Osceola you want to book. But in general, it’s 16, 18 or 21.

How long can I rent a vacation rental in Osceola for?

It really depends on the Osceola property. To look at a list of options offering extended stays, just type your dates and number of guests into Vrbo. You can enjoy having the place to yourself, along with home comforts like a fully-equipped kitchen, air conditioning and an outdoor space where the kids can burn off energy. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.

Does Vrbo offer discounts for vacation homes in Osceola?

Whether you’re after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some amazing deals and discounts on Vrbo. From mini stays to extended getaways, we’ve got the ideal place for your next Osceola escape.