Osceola holiday lettings

We found 103 holiday rentals — enter your dates for availability

Discover a selection of 6 homes and other holiday rentals in Osceola that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

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Head to the relaxing city of Osceola

Enjoy the entertainment and other features of Osceola. Travellers especially like the riverfront, bars and waterfalls in this relaxing and welcoming city. A holiday 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 attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Osceola a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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 looking for exciting outdoor activities or just want to spend some time taking in the scenery, Osceola is a great place to spend some time outside. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Franconia Sculpture Park (4.2 mi / 6.8 km)
  • Dalles of the Saint Croix River State Natural Area (5.9 mi / 9.5 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)

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 centre. If you can't find a flight that works for your travel itinerary, you could also fly into Minneapolis, MN (MSP-Minneapolis - St. Paul Intl.), which is 39 mi (62.8 km) away.

Frequently asked questions

What is the best area to stay in Osceola when booking a holiday rental?
When considering a holiday rental in Osceola, Wisconsin, the downtown area is a fantastic choice. This charming neighbourhood offers a quaint small-town atmosphere, making it great for those looking to unwind while still having access to local amenities. The downtown area is home to several lovely shops and eateries, allowing visitors to immerse themselves in the local culture.

Another appealing option is the area surrounding the St. Croix River. This picturesque setting not only provides stunning views but also offers outdoor activities such as hiking and fishing, making it ideal for nature enthusiasts. The nearby Cascade Falls is a must-see attraction, providing a beautiful spot for a leisurely stroll or a picnic.
How much does it cost to rent a holiday home in Osceola?
Prices for holiday 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 holiday 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, the area around the St. Croix River is particularly appealing. This picturesque river setting offers a variety of holiday rentals, often featuring beautiful views and direct access to the water. Many properties in this region come equipped with amenities such as private docks, outdoor decks, and fire pits, superb for enjoying summer evenings by the river.

In Osceola, visitors can also explore the scenic beauty of the surrounding landscape, which includes parks and trails for hiking and biking. The nearby Interstate State Park is a highlight, offering stunning rock formations and opportunities for water activities, including canoeing and kayaking. Rentals in this vicinity may also provide access to equipment for such activities, as well as spacious living areas and kitchens for family gatherings after a day of exploration.

Additionally, the local community boasts charming shops and eateries, giving travellers convenient options for dining and local experiences.
Where are the best Osceola ski resort rentals?
For the best ski resort rentals near Osceola, Wisconsin, consider looking towards the nearby town of Taylors Falls, which is approximately a short drive from local ski areas. This charming town offers a selection of holiday rentals, from cosy cabins located among the trees to more spacious homes suitable for families. Many of these properties feature amenities such as fully equipped kitchens, fireplaces, and outdoor decks, superb for enjoying the winter scenery.

Additionally, the nearby St. Croix River area provides opportunities for rentals with picturesque views and proximity to outdoor activities. Some properties in this region come with access to local hiking trails and cross-country skiing paths, allowing for a range of winter sports right on your doorstep. Many accommodations also offer conveniences like Wi-Fi and laundry facilities, making them well-suited for longer stays.

For a more vibrant setting, consider exploring options in the town of Hudson, which is a bit further afield but offers a lively downtown area filled with shops and eateries. Here, you can find a variety of rental properties, from modern apartments to traditional homes, often equipped with amenities such as hot tubs and game rooms, ideal for relaxing after a day on the slopes.
What is the most popular type of holiday rental accomodation in Osceola?
In Osceola, holiday houses are the most popular type of holiday rental, with around 18 available across the area. These homes typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families and larger groups. Many also come with outdoor spaces, such as decks or patios, great for enjoying the scenic views of the surrounding countryside. Additionally, several cabins, apartments, and cottages can be found, offering a variety of options for different preferences.
Are there any family house rentals in Osceola?
In Osceola, Wisconsin, there are several family-friendly house rentals available, making it a lovely destination for groups looking to enjoy the great outdoors together. Many of these homes can be found in scenic areas close to the St. Croix River, offering opportunities for fishing, kayaking, and hiking.

Properties often feature spacious living areas, fully equipped kitchens for preparing family meals, and comfortable bedrooms. Visitors might also find amenities like outdoor patios, fire pits for evening gatherings, and yards where children can play safely.

The locale provides easy access to local attractions such as the Interstate State Park, known for its stunning views and recreational activities. Additionally, the charming town centre boasts quaint shops and eateries, enhancing the overall experience for families.
Can I find long-stay holiday rentals in Osceola?
A long-stay holiday rental in Osceola is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Osceola?
In Osceola, Wisconsin, there are several pet-friendly house rentals available, providing a friendly setting for travellers with pets. Many of these holiday homes come equipped with essential amenities such as fully furnished kitchens, outdoor spaces for relaxation, and comfortable living areas, making them ideal for families or groups looking to enjoy their stay.

The area around Osceola offers a wealth of natural beauty and outdoor activities, with nearby parks and trails great for walks with pets. The scenic St. Croix River is also close by, providing opportunities for fishing, kayaking, and enjoying the picturesque landscape.
Are there any remote work holiday rentals in Osceola?
In Osceola, Wisconsin, there are numerous remote work holiday rentals available, with around 33 options to choose from. The area is known for its picturesque landscapes and outdoor activities, making it an appealing choice for those looking to balance work and leisure. Many of the properties come equipped with essential amenities for remote work, such as high-speed Wi-Fi, comfortable desks, and ergonomic chairs, ensuring a productive environment.

Travellers can also enjoy the charm of the local community, with cafes and shops nearby that offer a taste of Osceola's friendly atmosphere. Additionally, the stunning natural surroundings provide opportunities for hiking, fishing, and exploring the scenic St. Croix River, making it easy to unwind after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Osceola holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Osceola with parking available—perfect for families or travellers 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 rental amenities typically include kitchens, which allow guests to prepare their own meals, and decks or patios that provide outdoor space for relaxation. Many properties also feature fireplaces, great for cosy evenings after a day of exploring the area. Onsite parking is commonly available, making it convenient for those travelling by car. Additionally, many rentals offer desks, suiting those who might need to work during their stay.
When is the best time to visit Osceola for a holiday rental?
The best time to visit Osceola for a holiday rental is during the peak season from July to September. This vibrant period attracts visitors eager to enjoy the warm summer weather, which typically ranges from 15 to 30 degrees Celsius, great for outdoor activities like hiking, fishing, and canoeing on the beautiful St. Croix River.

July stands out as the most popular month for travellers, offering a lively option filled with local festivals and events that celebrate the charm of this quaint town. During this time, you can immerse yourself in the local culture and enjoy the scenic beauty that surrounds Osceola.

For those seeking a more budget-friendly option, consider visiting in December. While this month is outside the bustling summer season, it has its own unique allure. Osceola transforms into a picturesque winter wonderland, providing opportunities for cozy indoor activities and festive holiday experiences.

Ultimately, your choice comes down to whether you prefer the energetic buzz of summer adventures or the serene beauty of winter in Osceola.
How early should I book a Osceola holiday rental?
Book your Osceola holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Osceola?
In Osceola, visitors can enjoy a variety of attractions that showcase the natural beauty and charm of the area. The scenic St. Croix River is a highlight, offering opportunities for kayaking, fishing, and hiking along its banks. The nearby Interstate State Park features stunning rock formations and picturesque trails, great for outdoor enthusiasts looking to explore the local landscape.

The historic downtown area of Osceola is quaint, with unique shops and local restaurants that provide a glimpse into the community's culture. For those interested in history, the Osceola & St. Croix Valley Railway offers a nostalgic train ride through the picturesque countryside, making it a delightful experience for families and history buffs alike.
Can I change or cancel my Osceola home rental booking on Vrbo?
To find Osceola holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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