Osceola County Vacation Rentals, Florida: house rentals & more

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.

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FLASH SALE! Lovely Condo Just 1 Mile From Disney w/ Resort Pool, WiFi & More

Sleeps 6 · 2 bedrooms · 2 bathrooms

14Bed Mansion For 32. JumboTron Sports Bar! LED Dark Mini Golf! Luxury Decor!

Sleeps 32 · 14 bedrooms · 11 bathrooms

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Find out more about Osceola County

Why visit Osceola County

Exciting Theme Parks: Osceola County is close to some of Florida's most thrilling theme parks, perfect for family fun and adventure.
Outdoor Recreation: With picturesque lakes and urban parks, enjoy a variety of outdoor activities like hiking, fishing, and picnicking.
Charming Kissimmee: Explore the vibrant city of Kissimmee, known for its friendly locals and sunny weather.
Variety of Accommodations: Choose from cozy cabins to modern condos, catering to every traveler's needs.
Cultural Experiences: Immerse yourself in local culture through events, arts, and community activities.

Popular types of accommodation in Osceola County

Discover the perfect getaway in Osceola County with a variety of vacation rentals to suit your needs. Whether you prefer a spacious private vacation home, a cozy cabin, or a modern condo, we have options that cater to all travelers. For those seeking a resort experience near Orlando, our listings include stunning villas and relaxing resorts. Explore your ideal Osceola County vacation rental today!

Houses: The top choice among travelers in Osceola County, offering spacious, comfortable stays perfect for families and groups.
Condos: A popular option for visitors seeking modern amenities and convenient locations near attractions.
Villas: Ideal for those wanting a luxurious experience, featuring private pools and upscale furnishings.
Apartments: A practical choice for budget-conscious travelers, providing a home-like atmosphere.
Cottages: Quaint and charming, perfect for a cozy getaway close to nature.**

Top attractions in Osceola County

Osceola County, Florida, is a fantastic destination for families and outdoor enthusiasts alike. With an array of attractions including urban parks, picturesque lakes, and exciting entertainment arenas, there’s something for everyone. Explore cultural experiences and enjoy outdoor activities that cater to all ages. Whether you're traveling with family or seeking adventure, Osceola County offers a memorable vacation filled with fun and exploration.

Osceola Heritage Park: A vibrant urban park perfect for family outings, Osceola Heritage Park features beautiful green spaces, walking trails, and hosts various events throughout the year, creating a lively community atmosphere.
Silver Spurs Arena: This entertainment hub offers a thrilling array of events, from rodeos to concerts, ensuring a fun-filled experience for all ages. The lively atmosphere and family-friendly events make it a must-visit.
Fun Spot America: A dynamic theme park packed with exciting rides, games, and attractions, Fun Spot America promises a day of laughter and thrills for families, making it an unforgettable adventure.

Things to do recommended for couples

For a romantic experience in Osceola County, try the Congo River Golf or Pirate's Island Adventure Golf, both offering fun mini-golf adventures amidst family-friendly vibes. Don't forget Bonanza Golf & Gifts for a delightful combination of sport and romance, perfect for couples seeking memorable moments together.

Things to do recommended for families

Your family will have a blast at ESPN Wide World of Sports, where sports enthusiasts can enjoy exciting events. Dive into adventure at Island H2O Live!, a thrilling waterpark, and unwind at Shingle Creek Regional Park, a perfect spot for relaxation amidst nature.

Things to do recommended for groups

In Osceola County, groups can enjoy shopping and entertainment at Old Town, play a round of golf at Mystic Dunes Golf Club, or experience the thrilling performances at Medieval Times. These activities offer a fun mix of family-friendly and cultural experiences for everyone to enjoy.

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

When traveling with a group, family, pets, or seeking extended stays, it's important to prioritize your preferences during your search. Here are some helpful booking tips for Vrbo.

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 kids can be demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to attractions that are enjoyable for families.
Taking your pets with you to Osceola County: For many families, a vacation just isn't the same without their beloved pet. If this resonates with you, explore Vrbo listings that welcome pets. Many of these properties come equipped with feeding bowls and pet beds, ensuring that your furry friend feels just as comfortable as the rest of the family.
Planning for a long term stay visiting Osceola County: If you're in search of vacation rentals that offer special rates for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features 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, offers a delightful mix of family-friendly entertainment and outdoor adventures. Explore the vibrant city of Kissimmee, where sunny weather and friendly locals await. Just a stone's throw from the Orlando area, you'll find a wealth of recreational activities and relaxing rural living. Whether you seek thrilling theme parks or serene natural landscapes, Osceola County promises an unforgettable vacation experience for everyone.

Kissimmee: Kissimmee is a vibrant city in Osceola County, known for its family-friendly atmosphere and entertainment options. Nestled close to major theme parks, it serves as a central hub for tourists looking to experience the magic of Florida. Visitors can explore a variety of resorts, shopping centers, and local attractions, including iconic theme parks and stunning beaches. Kissimmee's lively downtown area offers excellent dining and entertainment, making it a delightful stop for travelers of all ages.
Four Corners: Four Corners is a charming area in Osceola County that combines family fun with outdoor adventures. This community is perfect for those looking to enjoy golf courses, resorts, and a plethora of recreational activities. With close proximity to theme parks and beautiful natural landscapes, Four Corners is an ideal destination for families seeking both relaxation and excitement. The area's welcoming atmosphere and variety of outdoor experiences make it a great spot to unwind and explore.
Celebration: Celebration is a picturesque community in Osceola County, designed with a unique blend of modern amenities and charming architecture. Known for its family-oriented environment, it offers a range of resorts, shopping areas, and golf courses. Visitors can stroll through the beautifully landscaped streets, enjoy local events, and savor delectable dining options. With nearby attractions like theme parks and sports stadiums, Celebration provides an enchanting backdrop for a memorable vacation.

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, opting for a longer 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.

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you'll receive OneKeyCash™ on the total booking amount. Being the organizer certainly has its perks! Become a member of our One Key rewards program to unlock exclusive savings and earn OneKeyCash™ on qualifying stays. Sign up today and begin your journey to savings!

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a user-friendly platform where you can easily create new trips, resume planning from where you left off, and manage your travel arrangements. You'll be able to see your saved or booked properties sorted into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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?

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.