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Osceola County vacation rentals

We found 33,921 vacation rentals — enter your dates for availability

Select from 3152 houses, 255 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.

Vacation rentals with weekly discounts - Osceola County

Showing deals for:Jun 12 - Jun 19

Image gallery for Stylish and Cozy Pool Home near Disney in a Gated Community

Newly surfaced pool facing conservation area!
9.4 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)

Stylish and Cozy Pool Home near Disney in a Gated Community

Kissimmee

8% off
Price is $459
$3,213 for 7 nights
All fees included
Stylish and Cozy Pool Home near Disney in a Gated Community

Find spaces that suit your style

Find out more about Osceola County

Why visit Osceola County

  • Family-friendly activities: Osceola County offers a variety of attractions perfect for families, ensuring fun for all ages.
  • Outdoor adventures: Explore urban parks, beautiful lakes, and hiking trails ideal for nature lovers and outdoor enthusiasts.
  • Proximity to theme parks: Enjoy easy access to famous theme parks, adding excitement to your vacation.
  • Charming accommodations: Choose from cozy cottages, villas, and vacation rentals for a comfortable stay.
  • Nearby beaches: Visit stunning beaches like Playalinda and Siesta Key for relaxation and fun in the sun.

Popular types of accommodation in Osceola County

Planning a getaway to Osceola County? The exciting part begins with selecting your perfect home away from home. Explore a variety of popular accommodations, including houses, villas, and condos. Whether you’re searching for cozy cottage vacation rentals or comfortable options with breakfast included, Osceola County has something for everyone. Discover your ideal vacation rental today and make unforgettable memories in this beautiful destination.

  • Houses: The top choice for travelers, these homes offer spacious accommodations perfect for families or groups seeking comfort and privacy.
  • Villas: A favored option for those looking for luxurious stays, villas provide upscale amenities and often come with pools.
  • Condos: Popular among visitors, condos offer a blend of convenience and community with access to shared facilities.
  • Apartments: A practical choice for solo travelers or couples, apartments provide essential comforts and a home-like atmosphere.
  • Cottages: Charming and cozy, cottages are ideal for a quaint getaway, perfect for couples or small families.**

Top attractions in Osceola County

Osceola County, Florida, offers a fantastic mix of family-friendly activities, outdoor adventures, and cultural experiences. Visitors can explore urban parks, beautiful lakes, and hiking trails, making it ideal for nature lovers. Nearby attractions like Playalinda Beach and Siesta Key provide additional opportunities for relaxation and fun. Whether you're seeking entertainment or a short excursion, Osceola County has something for everyone to enjoy during their vacation.

  • ChampionsGate Golf Club: A premier golf destination, ChampionsGate Golf Club offers a family-friendly atmosphere with beautiful courses designed for both novice and experienced golfers. Enjoy friendly service while taking in the scenic views and engaging in excursions around the lush landscapes.
  • Kissimmee Lakefront Park: This urban park provides a perfect blend of outdoor family fun and city scenery. Stroll along the lake, enjoy picnics, or take part in recreational activities while soaking up the sun and the vibrant local ambiance.
  • Fun Spot America: An exciting amusement park designed for adventure seekers, Fun Spot America features thrilling rides and outdoor games. Perfect for families, it promises a day filled with laughter, fun, and unforgettable memories.

Things to do recommended for couples

For a romantic getaway in Osceola County, explore the serene beauty of Lake Tohopekaliga with a sunset boat cruise. Indulge in a cozy dinner at a lakeside restaurant, and don't miss the enchanting stroll through the charming streets of Celebration, filled with delightful shops and vibrant scenery.

Things to do recommended for families

Families visiting Osceola County can enjoy thrilling rides at Walt Disney World, explore the adventurous Gatorland, and have fun at the interactive Orlando Science Center. Additionally, take a scenic airboat tour in the Everglades for an unforgettable wildlife experience.

Things to do recommended for groups

Explore the thrilling rides at Walt Disney World, or take a scenic airboat tour in the Florida Everglades. For a unique experience, visit the Osceola County Historical Society and immerse yourselves in local culture and history.

*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

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Osceola County with a group: Think about how many bedrooms you require, along with additional features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Osceola County with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with having 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 vacation isn't truly complete unless their furry companions are along for the journey. If you relate to this, explore Vrbo listings that welcome pets. Most of these pet-friendly properties offer feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Osceola County: If you're in search of vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the right filters, 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 criteria as well.

Where to stay in Osceola County

Osceola County, Florida, is a fantastic vacation spot for families and outdoor enthusiasts alike. With its sunny weather and friendly atmosphere, you can explore natural features, state parks, and family-friendly attractions. Don't miss the nearby theme parks, or consider a cozy cottage for a relaxing stay. Whether you’re seeking adventures or tranquil excursions, Osceola County offers a delightful blend of entertainment and nature in Central Florida.

  • Kissimmee: Kissimmee is a vibrant city nestled in Osceola County, known for its family-friendly atmosphere and entertainment options. The area is a favorite among tourists seeking a blend of relaxation and excitement. Visitors can explore numerous resorts, shopping areas, and mall centers, making it ideal for retail therapy. The proximity to famous theme parks, film studios, and beautiful beaches ensures a full itinerary. Whether you're enjoying a day at the parks or diving into local attractions, Kissimmee promises a memorable getaway.
  • Four Corners: Four Corners is a charming village located in Osceola County, perfect for families and outdoor enthusiasts. This area is renowned for its resorts and golf courses, offering plenty of options for relaxation and recreation. Visitors can enjoy the scenic beauty of nearby theme parks, film studios, and sports facilities, making it an ideal destination for both leisure and excitement. The outdoor activities available here will appeal to those looking to spend time in nature while still having access to fun attractions.
  • Celebration: Celebration is a picturesque city situated in Osceola County, known for its quaint charm and vibrant community. This area attracts families and business travelers alike, featuring a range of resorts, shopping areas, and mall centers. With easy access to renowned theme parks, film studios, and sports facilities, there's no shortage of entertainment options. Celebration's unique blend of leisure and business amenities makes it a perfect spot for visitors seeking a delightful blend of experiences and attractions.

Booking with Vrbo is simple

Are you aiming to save on your next adventure? Being flexible with your travel dates can help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Plan your group getaway by booking an eligible Vrbo and earn valuable OneKeyCash on your reservation. It truly pays to be the organizer. When you join our travel rewards program, One Key, you can immediately access member savings and earn OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides you with a convenient platform to plan new trips, manage your existing plans, or review and organize your bookings. The properties you've saved or reserved are categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/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 Cecile (4.9 mi / 8 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)

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?
One of the more in-demand neighborhoods to get an Osceola County vacation home is Poinciana. When you lock in your Vrbo vacation rental, you will have the entire place to yourself. That means you won't have to share it with anybody except for your favorite people.
What is the most popular type of vacation rental accommodation in Osceola County?
According to our research, villas are the most desirable property type in Osceola County. But naturally, everyone's idea of an awesome trip can differ. Vrbo has vacation homes in a variety of sizes and shapes, and we'll help you to find your perfect match.
How much does it cost to rent a vacation rental in Osceola County?
Several factors affect how much you pay for a vacation rental in Osceola County, such as the length of stay, season and type of property. But, all our vacation homes have something in common — amazing value. Simply add your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Osceola County?
Prices for beach houses in Osceola County may vary depending on the size and type of the property and time of year you're traveling. Simply enter your travel dates into Vrbo and the number of guests to view your rental options and prices. From there you can use our filters to tailor your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly vacation rentals in Osceola County?
Happily, yes. You'll have a choice of 801 vacation homes that welcome pets in Osceola County on Vrbo. Our furry kids also deserve a little time out, so simply use our search function for pet-friendly vacation rentals to book a perfect pad where your pup can lap up the fun.
Are there large group vacation rentals in Osceola County?
With 9,346 vacation rentals that can host 10 or more guests in Osceola County, you won't have to keep anyone off the invite list. From fun family get-togethers to special events like Thanksgiving or Christmas parties, Vrbo can help you find a large group rental to match the occasion.
What are the top attractions for families in Osceola County?
Keeping the kids entertained during your vacation in Osceola County is child's play with these fabulous family-friendly attractions:

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

Are there one-bedroom vacation rentals in Osceola County?
Yes, there are 912 one-bedroom properties in Osceola County to choose from. A one-bedroom vacation property is a great choice if it's just the two of you or if you're traveling alone. Add in more space, convenience and privacy than a hotel, and you've got yourself an unforgettable getaway.
Can I find two-bedroom vacation rentals in Osceola County?
Take off with your loved ones and relax in total privacy and comfort in one of the 1,587 two-bedroom vacation rentals Osceola County has to offer.
Are there vacation rentals with WiFi in Osceola County?
Whether you'd like to keep up with the news, make a video call or update your social media, there are 5,982 vacation homes with WiFi in Osceola County. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find vacation rentals with air conditioning in Osceola County?
Work out your travel dates and then make use of our filters to find vacation rentals with air conditioning in Osceola County on Vrbo. With 17,236 air-conditioned properties available, you can look forward to a cool and comfy break.
How old do you have to be to rent a vacation rental in Osceola County?
The minimum age is generally 16, 18 or 21. It can differ from one property to another on Vrbo, so look at the rules of your preferred Osceola County stay before booking your escape.
How long can I rent a vacation rental in Osceola County for?
The length of time you can rent a vacation rental in Osceola County is down to the property. Simply enter your desired travel dates to look at a list of options offering extended stays. With plenty of features like kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find somewhere just right to call your home away from home in Osceola County.
Does Vrbo offer discounts for vacation homes in Osceola County?
On Vrbo, we've got plenty of fantastic bargains and discounts for Osceola County. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're looking for a weekend retreat or an extended escape, Vrbo offers options for all budgets and styles.

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