Osceola vacation rentals

We found 102 vacation rentals — enter your dates for availability

Discover a selection of 6 homes and other 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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Find out more about Osceola

Why visit Osceola

  • Outdoor Adventures: Osceola offers stunning lakes and vibrant parks, perfect for hiking, fishing, and enjoying nature.
  • Romantic Getaways: The tranquil setting makes Osceola ideal for couples seeking a peaceful retreat.
  • Diverse Accommodations: Choose from cozy cabins to stylish apartments for a memorable stay tailored to your needs.
  • Nearby Attractions: Explore charming neighborhoods like Chisago City or take a short drive to family-friendly Oshkosh.
  • Friendly Vibes: Experience the warm, welcoming atmosphere that makes Osceola a delightful destination.

Popular types of accommodation in Osceola

Discover the perfect getaway in Osceola with our diverse vacation rentals, including private homes, cozy cabins, and stylish apartments. Whether you’re looking for a spacious home for rent with air conditioning or a comfortable Osceola apartment, we have options to suit every traveler’s needs. Enjoy the convenience and reassurance of choosing from a variety of accommodations, ensuring your stay in this charming area is both memorable and relaxing.

  • Houses: These are the top choice for visitors, offering spacious and comfortable accommodations perfect for families or groups.
  • Cabins: A close second, cabins provide a rustic and cozy atmosphere, ideal for those looking to connect with nature.
  • Apartments: Convenient and often centrally located, apartments are perfect for those seeking a home-away-from-home experience.
  • Cottages: Charming and quaint, cottages offer a delightful retreat for couples or small families.
  • Condos: These modern and stylish options provide amenities and a community feel, appealing to various travelers.**

Top attractions in and around Osceola

Osceola, Wisconsin, is perfect for outdoor enthusiasts and those seeking a romantic getaway. With its stunning lakes, vibrant urban parks, and nearby national and state parks, there's something for everyone to enjoy. Whether you're traveling with family, friends, or as a couple, the area's attractions provide a delightful blend of nature and city experiences, making it an ideal destination for your vacation.

  • Osceola & St. Croix Valley Railway: Experience a nostalgic ride on this historic railway, which offers scenic views and rich cultural vibes. The vintage coaches evoke the charm of a bygone era while you travel through picturesque landscapes.
  • Saint Croix River: Enjoy the breathtaking scenery along the Saint Croix River, perfect for outdoor activities such as kayaking, fishing, or simply relaxing by the water's edge. Its beauty provides a tranquil escape.
  • Interstate State Park: Discover adventure in this national park, known for its stunning landscapes and outdoor activities. Hike the trails, explore the unique geological formations, and immerse yourself in nature.

Things to do recommended for couples

Osceola offers charming experiences for couples, like a scenic hike at the nearby Interstate State Park or a romantic boat ride on the St. Croix River. Enjoy a cozy dinner at a local restaurant, followed by a stroll along the picturesque riverside, creating unforgettable memories together.

Things to do recommended for families

Families visiting Osceola can enjoy a thrilling day at Wild Mountain Waterpark, explore the scenic trails at Interstate State Park, and embark on a fun-filled adventure through the St. Croix River on a family-friendly boat tour, creating lasting memories together.

Things to do recommended for groups

Explore the scenic beauty of the St. Croix River with a group kayak tour or enjoy a fun-filled day at the Osceola & St. Croix Valley Railway. Don't miss the local shops and eateries for a taste of the community's charm.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

No matter if you're traveling with a group, as a family, bringing your pets, or seeking extended stays, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Osceola with a group: Think about how many bedrooms you'll require and whether you need amenities like a full kitchen or outdoor space for group activities. Thankfully, you can easily filter for these features and many others on Vrbo.
  • Traveling to Osceola with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, considering your distance to family-friendly attractions is a wise choice.
  • Taking your pets with you to Osceola: For many families, a vacation isn't truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties offer amenities like feeding bowls and pet beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Osceola: If you're searching for vacation rentals that offer discounts for stays of a month or longer, 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 preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Osceola

Osceola, Wisconsin, is a tranquil city perfect for outdoor and romantic vacations. Nestled in scenic surroundings, it offers friendly vibes and relaxing experiences. Explore nearby neighborhoods like Chisago City or take a short drive to Oshkosh for more family-friendly activities. Whether you're seeking excursions or a peaceful retreat, Osceola and its surroundings provide an ideal backdrop for your getaway.

  • St Croix Falls: Located 7 miles from Osceola, St Croix Falls is a picturesque city known for its stunning outdoor scenery and romantic atmosphere. Visitors flock to this charming destination for its variety of recreational activities, including skiing and exploring ski fields. The nearby attractions, such as the scenic lakes and the breathtaking St. Croix National Scenic Riverway, provide ample opportunities for hiking, picnicking, and enjoying nature. Whether you're wandering through its parks or taking in the views of the river, St Croix Falls is a perfect spot for those seeking adventure and relaxation alike.
  • Dresser: A mere 4 miles from Osceola, Dresser is a vibrant city that offers a fantastic blend of outdoor sports and recreational activities. Popular among skiing enthusiasts, Dresser features excellent ski fields and recreational areas that cater to both beginners and seasoned skiers. The proximity of beautiful lakes and the St. Croix National Scenic Riverway enhances the outdoor experience, making it an ideal location for fishing, boating, and hiking. With its friendly community vibe, Dresser is a great base for anyone looking to enjoy the splendors of the Wisconsin outdoors.
  • Taylors Falls: Situated 6 miles away from Osceola, Taylors Falls is a charming city that captivates visitors with its stunning natural beauty and romantic settings. Known for its outdoor activities, Taylors Falls offers access to ski fields, recreational areas, and breathtaking views of the St. Croix River. The nearby Taylors Falls Scenic Area is a must-visit, featuring dramatic cliffs and scenic trails, perfect for hiking and photography. Additionally, the area's theme park adds an element of fun for families. With its enchanting landscapes and outdoor adventures, Taylors Falls is a delightful destination for all ages.

Booking with Vrbo is a breeze

Are you hoping to save money on your next vacation? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a user-friendly area where you can plan new trips, continue from where you last stopped, or manage your travel arrangements. You'll have easy access to your saved or booked properties, organized into categories like Potential, Upcoming, and Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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)
  • St Croix National Scenic Riverway (7.2 mi / 11.6 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)

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)
  • Green Lake (9.6 mi / 15.4 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 best area to stay in Osceola, Wisconsin, United States of America when booking a vacation rental?
When planning a vacation in Osceola, Wisconsin, one of the best areas to consider for a rental is the charming downtown district. This area offers a delightful blend of local shops, restaurants, and easy access to the scenic St. Croix River. Staying here puts you within walking distance of attractions like the historic Osceola & St. Croix Valley Railway, where you can enjoy a nostalgic train ride through beautiful landscapes. Additionally, the nearby Cascade Falls Park provides a serene escape with picturesque views of the waterfall and trails for hiking.
How much does it cost to rent a vacation home in Osceola?
Prices for vacation rentals in Osceola vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Osceola to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Osceola vacation house rentals?
You can find great discounts on house rentals in Osceola on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Osceola?
For renting a beach house in Osceola, Wisconsin, travelers should focus on the scenic areas surrounding the Apple River and nearby lakes. The Apple River offers numerous spots where visitors can find charming waterfront cabins and homes that feature amenities such as private docks, outdoor fire pits, and spacious decks for enjoying the beautiful river views. Many properties in this area come equipped with kayaks or canoes, making it easy for families to enjoy water activities right from their doorstep.

Further north, the properties near Lake Wapogassett provide another excellent option for beach house rentals. Here, travelers can find vacation homes with sandy beaches, picnic areas, and sometimes even sandy volleyball courts. These homes often include modern kitchens and outdoor grills, superb for family gatherings and summer barbecues.

Additionally, the surrounding natural beauty provides ample opportunities for hiking and exploring. Rentals in this region often have access to local parks, hiking trails, and fishing spots, enhancing the outdoor experience for guests.
Where are the best Osceola ski resort rentals?
For ski rentals near Osceola, Wisconsin, travelers should consider accommodations in the nearby town of St. Croix Falls, just a short drive away from the ski areas. This charming town offers a variety of properties, including cozy cabins and inviting lodges that often feature amenities like fireplaces, full kitchens, and outdoor decks superb for enjoying the natural surroundings after a day on the slopes.

In the vicinity of Osceola, the area around the scenic St. Croix River provides additional options, where visitors can find vacation rentals with beautiful views and easy access to nature trails for winter hiking or snowshoeing. Many properties in this region are equipped with modern conveniences such as Wi-Fi, entertainment systems, and laundry facilities, suiting families and groups seeking comfort during their stay.

For those looking to explore beyond skiing, the nearby Interstate State Park offers stunning views of the river and opportunities for outdoor activities. Rentals in this area often provide a peaceful retreat with access to local dining options and shops, making it an ideal base for those enjoying winter sports and the beauty of the Wisconsin landscape.
What is the most popular type of vacation rental accomodation in Osceola?
In Osceola, vacation houses are quite popular, with several available throughout the area. These properties typically offer spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many vacation houses also feature outdoor spaces like patios or decks, great for enjoying the scenic surroundings. Alongside houses, there are also several cabins and cottages, which provide a cozy, rustic experience for those looking to immerse themselves in nature. Apartments are available as well, offering a more compact option with essential amenities for travelers seeking convenience.
Are there any family house rentals in Osceola?
In Osceola, Wisconsin, there are several family-friendly house rentals available, making it a great spot for families to enjoy a getaway. The town offers a variety of homes that often include spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and explore. Many properties also come with amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for everyone.

Visitors can take advantage of nearby attractions like the scenic St. Croix River, great for outdoor activities such as fishing and kayaking, or explore local parks that provide ample space for picnics and recreation.
Can I find long-stay vacation rentals in Osceola?
A long-stay vacation rental in Osceola is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Osceola?
In Osceola, Wisconsin, there are several pet-friendly house rentals available, superb for travelers looking to enjoy a getaway with their furry companions. Many of these vacation homes come equipped with amenities such as full kitchens, spacious living areas, and outdoor spaces where pets can roam freely. Some properties may even feature fenced yards or nearby trails for walking and exploring with pets.

The area is surrounded by beautiful natural landscapes, including the scenic St. Croix River, which provides opportunities for outdoor activities like kayaking and fishing. Additionally, nearby parks and wooded areas offer great spots for hiking and enjoying nature walks with pets.
Are there any remote work vacation rentals in Osceola?
In Osceola, Wisconsin, there are some remote work vacation rentals available, with around 11 options to choose from. These rentals provide a conducive environment for remote work, featuring amenities such as free Wi-Fi, dedicated desks, and comfortable desk chairs. Many properties also offer spacious living areas for relaxation after a productive workday. The scenic surroundings of Osceola, with its beautiful rivers and parks, provide a refreshing backdrop for those balancing work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Osceola vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Osceola with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Osceola?
In Osceola, popular vacation rental amenities cater to travelers seeking comfort and convenience. Most rentals feature well-equipped kitchens, allowing guests to prepare their own meals. Many properties also include decks or patios, providing outdoor spaces to relax and enjoy the scenic surroundings. A fireplace is a common amenity, adding warmth and a cozy atmosphere, especially during cooler months. Onsite parking is typically available, making it easy for guests to access their accommodations. Additionally, many rentals offer a desk, ideal for those needing a workspace during their stay.
When is the best time to visit Osceola for a vacation rental?
The peak travel season in Osceola typically runs from July to September, making it the most vibrant time to explore this charming town. During these summer months, visitors can relish in a lot of outdoor activities, from kayaking on the scenic St. Croix River to hiking the lush trails of nearby state parks. The warm temperatures, often reaching the 70s and low 80s Fahrenheit, provide an inclusive setting for travelers, ensuring a memorable experience filled with sunshine and fun.

July stands out as the most popular month for travelers, when Osceola buzzes with excitement and various local events. This is the great time to indulge in outdoor festivals, farmers' markets, and community gatherings, allowing visitors to immerse themselves in the local culture while enjoying the area's natural beauty.

For those looking for a more budget-friendly option, consider planning your visit in December. Although it's the low season, the winter months bring a unique charm to Osceola, with opportunities for cozy indoor activities and winter sports nearby. You can savor the peaceful ambiance that comes with fewer crowds while enjoying the festive spirit of the holiday season.
How early should I book a Osceola vacation rental?
Book your Osceola vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Osceola, Wisconsin, United States of America?
In Osceola, visitors can explore a variety of attractions that showcase the area's natural beauty and local charm. The scenic St. Croix River offers opportunities for kayaking and fishing, with several access points along the riverbanks. The nearby Interstate State Park is a popular destination for hiking and features unique geological formations, as well as picturesque views of the river.

Osceola's downtown area boasts quaint shops, cafes, and local eateries that reflect the community's small-town atmosphere. The historic Osceola & St. Croix Valley Railway provides an engaging way to experience the region's history and scenic landscapes through seasonal train rides.

Additionally, the Osceola Village Park is a nice spot for relaxation and outdoor activities, featuring walking trails and picnic areas.
Can I change or cancel my Osceola home rental booking on Vrbo?
To find Osceola vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Osceola vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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