Osceola County vacation rentals

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Select from 17942 houses, 1996 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

Find out more about Osceola County

Find out more about Osceola County

Why visit Osceola County

  1. Disney Theme Parks: Osceola County is home to iconic Disney parks, providing magical experiences for families and visitors of all ages.
  2. Outdoor Adventures: Enjoy a variety of outdoor activities, from scenic lakes to urban parks, perfect for nature enthusiasts.
  3. Family-Friendly Attractions: With numerous attractions and activities, Osceola County caters to families looking for fun and memorable experiences.
  4. Charming Neighborhoods: Explore vibrant local communities that offer unique shops, dining, and cultural experiences.
  5. Diverse Accommodations: Choose from an array of lodging options including vacation homes, villas, and cozy cottages to suit every traveller's needs.

Popular types of accommodation in Osceola County

If you're considering a getaway to Osceola County, you’ll find a variety of accommodations to suit your needs. Our most popular options include houses, villas, and condos. Whether you're looking for cozy holiday cottages, rentals with breakfast, or unique cottage rentals across the United States, we have something for everyone. Enjoy the comfort of height beds and explore all that this beautiful area has to offer!

  • Houses: These are the top choice for visitors to Osceola County, offering spacious and comfortable settings ideal for families or groups.
  • Villas: Second in popularity, villas provide a luxurious and private experience, often featuring pools and upscale amenities.
  • Condos: Condominiums rank third, combining convenience with modern living, perfect for those seeking a home-away-from-home feel.
  • Apartments: Apartments are fourth, offering practical and budget-friendly options for solo travellers or couples.
  • Cottages: Finally, cottages provide a quaint and charming atmosphere, ideal for a cozy getaway.**

Top attractions in Osceola County

Osceola County offers a fantastic vacation experience for families and outdoor enthusiasts alike. With a variety of attractions such as urban parks, scenic lakes, and entertainment facilities, there's something for everyone to enjoy. Whether you're seeking cultural experiences, outdoor adventures, or family-friendly activities, Osceola County is a great destination to explore and create lasting memories.

  1. ChampionsGate Golf Club: Experience world-class golfing in a welcoming atmosphere, perfect for families and golf enthusiasts alike. Enjoy meticulously designed courses and friendly staff, making it an ideal spot for a fun day out with loved ones.
  2. Kissimmee Lakefront Park: A beautiful urban park offering scenic views of the lake, perfect for picnics and outdoor activities. Enjoy playgrounds, walking trails, and a vibrant atmosphere, ideal for family outings.
  3. Silver Spurs Arena: An exciting venue for family entertainment, hosting a variety of events ranging from rodeos to concerts. Experience the lively atmosphere and enjoy a night of fun and excitement.

Things to do recommended for couples

Experience a romantic getaway in Osceola County, Florida, with delightful mini-golf at Congo River Golf, Pirate's Island Adventure Golf, or Bonanza Golf & Gifts. Enjoy the family-friendly, adventurous atmosphere while sharing laughter and friendly competition with your partner!

Things to do recommended for families

Your family vacation in Osceola County promises fun with adventures at ESPN Wide World of Sports, thrills at Island H2O Live! waterpark, and relaxation at Shingle Creek Regional Park. Enjoy a blend of sports, water fun, and nature for an unforgettable experience!

Things to do recommended for groups

Groups visiting Osceola County can enjoy shopping and entertainment at Old Town, experience outdoor fun at Mystic Dunes Golf Club, and immerse themselves in culture and family entertainment at Medieval Times. Each venue offers a unique vibe perfect for group bonding and making lasting memories.

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

When you're planning a trip—whether it's with a group, your family, or pets, or if you're seeking extended stays—it's important to refine your search based on your specific needs. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Osceola County with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Osceola County with young kids: Traveling with young children can present some challenges. It's important to prioritize their comfort and safety, along with suitable amenities 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 families, a getaway wouldn’t feel complete without their furry companions. If you can relate to this, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Osceola County: If you're seeking vacation rentals with special offers for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. You might also want to include amenities like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay in Osceola County

Osceola County, Florida, offers a delightful vacation experience perfect for families and outdoor enthusiasts alike. With its sunny weather and friendly atmosphere, you'll find fantastic vacation spots like the iconic Disney theme parks and charming local attractions. Enjoy relaxing excursions, explore vibrant neighborhoods, and create unforgettable memories in this family-friendly destination. Whether you're seeking adventure or relaxation, Osceola County has something for everyone, making it an ideal getaway for Canadian travellers.

  • Kissimmee: Kissimmee is a vibrant city located in Osceola County, renowned for its family-friendly atmosphere and entertainment options. Situated conveniently near major highways, it is the gateway to numerous attractions, including world-famous theme parks. Visitors can enjoy a variety of activities, from shopping at bustling malls to relaxing at luxurious resorts. The city's proximity to beautiful beaches and film studios adds to its allure, making it a perfect spot for those seeking adventure and relaxation alike.
  • Four Corners: Four Corners is a charming village located in Osceola County, ideal for families and outdoor enthusiasts. This quaint area is easily accessible and offers an array of recreational activities, including golf at well-maintained courses. It serves as a peaceful retreat while being close to exciting attractions like theme parks and stadiums. Whether you're looking to unwind at a resort or explore the local outdoor scenery, Four Corners provides a welcoming atmosphere for all visitors.
  • Celebration: Celebration, a picturesque city in Osceola County, invites visitors to experience its enchanting streets and unique charm. Known for its strong sense of community, it offers a delightful mix of family-friendly activities and entertainment options. Explore the quaint shopping areas or enjoy a round of golf at nearby courses. With close proximity to popular theme parks and stadiums, Celebration combines leisure with excitement, making it a must-visit destination for tourists seeking a balanced vacation experience.

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient area for you to plan new adventures, refine your arrangements, or manage your reservations. The properties you’ve saved or booked are now organized into categories: Potential, Upcoming, or Current Trips. To discover Trip Boards, please 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 Animal Kingdom® Theme Park (12.1 mi / 19.5 km)
  • Universal Orlando Resort (13 mi / 21 km)
  • Universal Studios Florida (13.4 mi / 21.6 km)
  • Walt Disney World® Resort (13.6 mi / 21.9 km)
  • Magic Kingdom® Park (13.7 mi / 22 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)
  • Austin-Tindall Regional Park (8.3 mi / 13.4 km)
  • Bill Frederick Park (15.1 mi / 24.3 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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