Why Choose Rent By Owner for your Osceola County Accommodations?
What makes our Accommodations special?
Best Times to Visit Osceola County
When should you plan your Accommodations stay?
Choosing the optimal time to visit here ensures you experience the best of what this destination has to offer, whether you're seeking pleasant weather, local events, or fewer crowds, making it an ideal choice for your next vacation in Osceola County, Florida, USA.
Peak Season Highlights
Winter (December to February)
During the winter months, visitors flock here to escape colder climates, making it a bustling season for the area. Expect lively surroundings and higher demand for accommodations.
Summer (June to August)
The summer season attracts many travelers seeking warm weather and outdoor activities. This is when demand peaks for resort-style accommodations and vacation rentals.
Off-Season Highlights
Spring (March to May)
In spring, the area experiences a slight slowdown with fewer visitors, offering more available properties and greater flexibility for your plans.
Fall (September to November)
During fall, the region sees reduced visitor numbers, providing an ideal opportunity to enjoy quieter accommodations and more personalized experiences.
Weekly Weather Forecast for Osceola County
How to Book Your Osceola County Accommodations
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Osceola County
Common Accommodations Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor swimming pools available at many rentals in the area, perfect for relaxing after a day of exploring.
- Take advantage of private or shared patios and decks to unwind while soaking up the Florida sunshine.
- Benefit from spacious yards and gardens ideal for outdoor activities or family gatherings.
- Make use of grilling areas equipped with barbecue facilities for outdoor dining experiences.
- Experience the convenience of on-site sports courts such as tennis or basketball for active recreation.
- Relax in shaded gazebo or pavilion areas designed for outdoor lounging and socializing.
- Utilize nearby parks and trails accessible from your accommodation for outdoor adventures and nature walks.
Top Attractions Around Osceola County
What attractions are nearby?
In this vibrant region, you can enjoy a variety of outdoor activities and entertainment options nearby, making it an ideal destination for exploring local parks, cultural attractions, and recreational spots that cater to all interests during your stay.
Family Activities
- Visit Gatorland Experience the region's unique wildlife attraction that offers family-friendly shows and up-close encounters with alligators and crocodiles.
- Explore Disney’s Magic Kingdom Park Delight in a visit to this iconic theme park, perfect for creating memorable moments with attractions suitable for all ages in the area.
- Discover Fun Spot America Enjoy thrilling rides, go-kart racing, and arcade games at this popular amusement park designed for family entertainment within the region.
- Enjoy Lake Tohopekaliga Relax or participate in water-based activities like fishing and boating at this scenic lake, a favorite spot for family outings nearby.
Adult Activities
- Wildlife Watching Tours: Experience the area's rich biodiversity with guided wildlife tours, perfect for observing native animals in their natural habitat.
- Golfing Experiences: Enjoy a round of golf at some of the region's premier courses, offering scenic views and challenging play for enthusiasts of all skill levels.
- Local Breweries and Wineries: Discover the vibrant craft beverage scene by visiting local breweries and wineries that showcase regional flavors and brewing traditions.
- Fishing Excursions: Take advantage of the area's waterways with fishing trips that cater to anglers seeking relaxation or adventure amidst stunning surroundings.
Other Places to Stay in Osceola County, FL
Osceola County Travel Tips
How Can You Make the Most of Your Stay?
- Explore local attractions Take advantage of the area's renowned outdoor activities and entertainment options to fully enjoy your stay in this popular destination.
- Plan ahead for peak seasons Book your accommodations early during busy times to secure the best properties and avoid last-minute availability issues.
- Discover hidden gems Venture off the beaten path to find unique dining spots, shops, and experiences that showcase the area's authentic charm.
- Utilize local transportation Make use of available transit options or shuttle services to navigate efficiently and maximize your time exploring this vibrant region.
Transportation Options
- Rental Car Services: Major companies like Enterprise, Hertz, and Avis operate in the area, offering convenient transportation options for exploring Osceola County at your own pace.
- Public Transit: The local transit authority provides bus services that connect key locations within the region, making it easy to get around without a vehicle.
- Taxi and Rideshare: Taxis and rideshare services like Uber and Lyft are readily available, providing flexible transportation options directly from your chosen accommodations.
- Shuttle Services: Several private shuttle providers offer scheduled routes and private charters to popular destinations within this vibrant destination.
Local Customs Options
- Southern Hospitality: Visitors here often notice a warm and welcoming attitude that reflects the region’s tradition of friendly hospitality, making your stay more comfortable.
- Local Festivals: Engaging in seasonal festivals and community events showcases the area’s vibrant cultural expressions and deep-rooted customs.
- Traditional Cuisine: Enjoying regional dishes offers insight into the area's culinary heritage, often featuring fresh local ingredients and time-honored recipes.
- Respect for Nature: A strong appreciation for outdoor spaces and conservation efforts encourages visitors to observe eco-friendly practices during their visit.
Frequently Asked Questions about Osceola County Accommodations
1. What are the top Accommodations in Osceola County?
There are a lot of options in Osceola County. If you plan on staying in the Osceola County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Accommodations in Osceola County:
- Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
- 4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee off Us192
- Water View - Pool & Spa - 3.5 miles to Disney - BBQ
- Amazing villa close to Disney with 5* Reviews
- Quiet, Clean, Disney-3.5 miles, Well kept home! Free Pool/spa Heat!
- Conservation View - Hot Tub - Free Pool Heat - Very Private
- BEAUTIFUL LAKEVIEW TOWNHOME, 5 MILES TO DISNEY. FULLY EQUIPED
- Our DisneyDreamVilla - minutes to DisneyWorld!
- Close to Disney! NO Extra Fees! Gated! Clean & Comfy! Family Friendly!
- Family friendly, 10 mins to Disney, WIFI, Resort style amenities, Backyard pool
2. How many Accommodations are available in Osceola County?
Currently, the total number of properties listed by RBO in 2026 is over 40426 in the Osceola County area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Osceola County.


























