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Osceola County vacation rentals

We found 34,290 vacation rentals — enter your dates for availability

Select from 3152 houses, 260 apartments, and other vacation rentals to find the perfect place for your stay in Osceola County. Whether you’re staying in a vacation home with your kids or with friends, you'll have the amenities you expect and more, such as air conditioning and a TV. Whatever you're looking for, you'll find a rental to meet everyone's needs, including accessible or non-smoking choices.

Popular cities in Osceola County

Vacation rentals with weekly discounts - Osceola County

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Find out more about Osceola County

Why visit Osceola County

  • Proximity to Disney: Osceola County is just a stone's throw away from the magical world of Disney, making it an ideal base for family adventures.
  • Outdoor Activities: Enjoy a variety of outdoor pursuits, from exploring serene lakes to visiting urban parks, perfect for families and nature enthusiasts.
  • Charming Neighborhoods: Discover delightful local neighbourhoods that offer a warm, welcoming atmosphere and unique experiences.
  • Diverse Accommodation Options: Choose from cozy cabins, private vacation homes, or modern condos to suit every traveler's needs.
  • Friendly Locals: Experience the hospitality of Osceola County's residents, adding to the overall charm of your visit.

Popular types of accommodation in Osceola County

Planning a getaway to Osceola County? The exciting part is finding the perfect place to stay. From houses and charming villas to modern condos, there's a range of options to suit every traveller's needs. Whether you're seeking a cozy cabin rental or looking for monthly accommodations, Osceola County has something for everyone. Discover your ideal vacation rental and make your trip unforgettable.

  • Houses: This is the top choice for visitors to Osceola County, offering spacious and comfortable stays for families and groups seeking a home-like experience.
  • Villas: A luxurious option, these stylish retreats provide ample space and upscale amenities for an indulgent holiday.
  • Condos: Perfect for couples or small families, these convenient accommodations offer a blend of comfort and modern living.
  • Apartments: A practical choice for those looking for a cozy and functional base while exploring the area.
  • Cottages: These quaint hideaways provide a charming atmosphere for a peaceful getaway.**

Top attractions in Osceola County

Osceola County offers a delightful vacation spot for families and outdoor enthusiasts alike. With attractions like urban parks, serene lakes, and entertainment arenas, there’s something for everyone to enjoy. Whether you're looking for cultural experiences or fun family activities, Osceola County has it all. Be sure to explore the local points of interest to make the most of your visit.

  • ChampionsGate Golf Club: Experience a premier golfing destination with beautifully designed courses and a welcoming atmosphere. Ideal for families and groups, it offers excursions that cater to all skill levels while surrounded by friendly staff and stunning landscapes.
  • Kissimmee Lakefront Park: Enjoy a vibrant urban park perfect for families, featuring scenic waterfront views, picnic areas, and walking trails. It’s a great spot for outdoor activities amidst the lively city vibe of Kissimmee.
  • Fun Spot America: Dive into a world of adventure at this amusement park, offering thrilling rides and attractions for all ages. It's a fantastic place for family fun outdoors, ensuring an exciting day filled with laughter.

Things to do recommended for couples

For a memorable couple's getaway in Osceola County, enjoy a round of mini-golf at Pirate's Island Adventure Golf, Bonanza Golf & Gifts, or Congo River Golf. Each offers a fun, adventurous atmosphere perfect for creating lasting memories together.

Things to do recommended for families

Your family will have a blast at ESPN Wide World of Sports Complex, soaking up the sports atmosphere. Dive into fun at Island H2O Live. waterpark for entertainment and adventure. For some thrill, head to Kissimmee Go-Karts for an exciting karting experience.

Things to do recommended for groups

Explore vibrant Old Town for shopping and entertainment, challenge your group at Mystic Dunes Golf Club for a round of golf, and enjoy a captivating evening at Medieval Times, where culture and drama come alive. Osceola County offers unforgettable experiences for everyone in your group.

*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 County

If you're planning a trip with friends, family, pets, or if you're interested in extended stays, be sure to apply the appropriate filters to match your needs. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Osceola County with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Osceola County with young kids: Traveling with young kids can be quite the task. It's important to prioritize their comfort and safety, along with finding amenities that are suitable for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Osceola County: For many, a family getaway wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Osceola County: If you're searching for vacation rentals that offer discounts for longer stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Osceola County

Osceola County, Florida, is a fantastic destination for family-friendly vacations, offering a delightful mix of entertainment and outdoor activities. Explore charming neighborhoods and enjoy sunny weather while visiting scenic lakes. With close proximity to the magic of Disney, it's the perfect spot for a memorable getaway. Friendly locals and relaxing excursions make Osceola County an ideal choice for an unforgettable holiday experience.

  • Kissimmee: Nestled in the heart of Osceola County, Kissimmee is a vibrant city that serves as a gateway to family-friendly entertainment. Known for its diverse resorts and bustling shopping areas, this city offers a blend of leisure and excitement. Visitors can easily access renowned theme parks and film studios, providing endless fun for all ages. Whether you're exploring the nearby beaches or indulging in retail therapy at the shopping mall, Kissimmee guarantees a memorable vacation experience.
  • Four Corners: Four Corners is a charming village located at the intersection of several major highways, making it a convenient spot for families and outdoor enthusiasts. With a focus on recreation, this area boasts beautiful golf courses and luxurious resorts that attract visitors seeking relaxation and adventure. Four Corners is also a stone's throw away from popular theme parks and stadiums, ensuring that there's never a dull moment. Whether you're teeing off or enjoying a family outing, this village offers the perfect backdrop for your Florida getaway.
  • Celebration: Designed with a picturesque charm, Celebration is a unique city that emphasizes community and entertainment. This vibrant locale features delightful shopping areas and golf courses, perfect for families and business travellers alike. With easy access to theme parks and film studios, Celebration's attractions cater to all interests. Stroll through the scenic streets, enjoy local dining options, and take in the stunning architecture that reflects the area's Disney-inspired roots. Celebration promises a delightful and enriching vacation experience.

Booking with Vrbo is simple

Are you hoping to save on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, choosing to book a longer stay can lead to considerable savings. 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.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan your upcoming adventures. You can easily start new trips, pick up from where you last left off, and organize all your travel plans in one place. Any properties you've saved or booked before are now conveniently located under Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Osceola County getaway

Experience the unique character of Osceola County with a stay in a vacation home rental. You'll find plenty to explore during your stay in the area. Walt Disney World® Resort and Old Town are just a couple of the must-sees. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Osceola County

Do you want to discover attractions to see while you're in town? Venture out of your vacation home and experience everything that makes Osceola County a fun place to get away. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Epcot® (10.2 mi / 16.4 km)
  • Disney's Hollywood Studios® (10.3 mi / 16.6 km)
  • Disney's Animal Kingdom® Theme Park (12.1 mi / 19.5 km)
  • Universal’s Volcano Bay (12.4 mi / 19.9 km)
  • Universal Orlando Resort (13 mi / 21 km)
  • Universal Studios Florida (13.4 mi / 21.6 km)

Exploring the natural features in Osceola County

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Osceola County is a great place to spend some time outside. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Kissimmee Lakefront Park (0.2 mi / 0.3 km)
  • Osceola Heritage Park (2.4 mi / 3.9 km)
  • Lake Tohopekaliga (6.1 mi / 9.9 km)
  • Lake Bryan (7.5 mi / 12.1 km)
  • Little Lake Bryan (8.1 mi / 13.1 km)
  • Austin-Tindall Regional Park (8.3 mi / 13.4 km)

Transportation to and around Osceola County

Fly into Kissimmee, FL (ISM-Kissimmee Gateway), the closest airport, located 1.8 mi (2.9 km) from the city center.

If you'd rather travel by train, the main station serving the city is Kissimmee Station. Walk to nearby metro transportation at Tupperware Station or Poinciana Station and easily see more of the city.

Frequently asked questions

What is the best area to stay in Osceola County when booking a vacation rental?
Among the more in-demand neighborhoods to find an Osceola County vacation home is Poinciana. When you book your vacation rental with Vrbo, you'll have the entire place to yourselves. That means you won't have to share it with anyone apart from your people.
What is the most popular type of vacation rental accommodation in Osceola County?
The most in-demand types of vacation rentals in Osceola County are houses. Hoping for something different? Vrbo has many options to match our guests' needs, so you'll see vacation properties in all shapes and sizes. The ideal home away from home is waiting for you — discover yours today.
How much does it cost to rent a vacation rental in Osceola County?
The average price for a vacation home in Osceola County is determined by a number of factors, such as length of stay, season and property type. Whether you'd like a sprawling villa with lots of bedrooms or a cozy cottage for you and your other half, just add your dates of travel to discover stays with great value.
How much does it cost to rent a beach house in Osceola County?
The average price for a vacation home close to the beach in Osceola County will depend on when you're going and the style and size of property you're searching for. You can find prices quickly and easily on Vrbo by entering your destination and travel dates. Then use our filter tool to choose the number of bedrooms and amenities that you prefer, like WiFi, air conditioning and a hot tub.
What are popular rental amenities in Osceola County?
When it comes to rental amenities that people are searching for in Osceola County, a microwave oven, a fridge and off-street parking options rank highest. With Vrbo vacation homes, you'll find options to match your style and taste, whether you're vacationing with your partner, your family or even pets.
Are there large group vacation rentals in Osceola County?
Osceola County has 7,124 vacation properties that can fit 10 or more guests. These properties come with the privacy and space you need to enjoy good times with your nearest and dearest.
What are the top attractions for families in Osceola County?
Keep the kids entertained at these fantastic family-friendly attractions in Osceola County:

  • Alligator Lake
  • Royal St. Cloud Links
  • Lake Tohopekaliga

Can I find two-bedroom vacation rentals in Osceola County?
Choose from 1,357 two-bedroom properties in Osceola County. Put your little ones in the second room or maybe fill it with a couple of your besties. There's ample space for whoever's fortunate enough to be joining your journey.
Are there vacation rentals with WiFi in Osceola County?
Choose from 5,340 vacation rentals with WiFi in Osceola County. If you want to disconnect from daily life during your break, but still want to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How old do you have to be to rent a vacation rental in Osceola County?
It's advisable to check with the Osceola County vacation home you want on Vrbo as the age limit varies. However, it's normally 16, 18 or 21.
How long can I rent a vacation rental in Osceola County for?
The length of time you can book a vacation rental in Osceola County is down to the property. Just enter your preferred dates to look at a list of options offering extended stays. With tons of amenities such as laundries and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find a perfect place to call your home away from home in Osceola County.

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