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Osceola County Luxury Rentals

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Osceola County Pet Friendly Vacation Rentals

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10.0 (6 Reviews)
House
Minnie Heaven
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Why Choose Rent By Owner for your Osceola County Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Osceola County

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience, as understanding the region’s seasonal patterns helps you find the perfect vacation rentals in Osceola County, Florida, USA, that suit your desired weather and activities.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, you'll enjoy mild weather and an influx of visitors seeking escape from colder climates, making this the busiest time for booking vacation rentals here.

Average Temperature Daytime: 75°F - Nighttime: 55°F
spring
Spring Break (March to April)

This is a popular period when families and travelers flock to the region, ensuring high demand for vacation rentals as everyone looks to take advantage of springtime adventures.

Average Temperature Daytime: 78°F - Nighttime: 58°F

Off-Season Highlights

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Summer (June to August)

While summer can be busy, early or late in the season offers fewer crowds, with warm temperatures that are perfect for enjoying outdoor activities at your vacation rental.

Average Temperature Daytime: 89°F - Nighttime: 70°F
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Fall (September to November)

Autumn provides a quieter experience with pleasant weather, making it an ideal time to book your vacation rental without the peak season prices and crowds.

Average Temperature Daytime: 82°F - Nighttime: 62°F

Weekly Weather Forecast for Osceola County

How to Book Your Osceola County Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Osceola County

More Top-Rated Vacation Rentals in Osceola County Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

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 a private outdoor swimming pool to relax under the Florida sun.
  • Take advantage of spacious patios or decks perfect for outdoor dining and entertaining.
  • Explore lush gardens and landscaped yards that add charm to your stay.
  • Make use of outdoor grilling facilities for flavorful barbecues with family and friends.
  • Benefit from access to tennis courts or other recreational sports amenities nearby.
  • Relax in shaded lanai areas designed for comfortable outdoor lounging.
  • Discover community amenities such as golf courses or walking trails integral to the region’s outdoor living appeal.

Top Attractions Around Osceola County

What attractions are nearby?

Within this vibrant region, you can enjoy a variety of outdoor activities and family-friendly attractions that showcase the best of Osceola County, Florida, offering a memorable experience just moments from your vacation rentals.

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Family Activities

  • Walt Disney World Resort: Experience the magic of world-famous theme parks, perfect for family fun and creating unforgettable memories in this renowned destination within the area.
  • Gatorland Orlando: Discover a thrilling wildlife park where your family can get up close with alligators and crocodiles, offering an educational adventure right here in the region.
  • Silver River State Park: Explore the natural beauty of this scenic park with hiking, kayaking, and wildlife viewing opportunities suitable for all ages in this outdoor haven.
  • SeaWorld Orlando: Enjoy interactive exhibits, shows, and rides at this marine-themed amusement park, providing family-friendly entertainment in this vibrant local attraction.
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Adult Activities

  • Visit Disney's Theme Parks: Experience the magic at world-renowned Disney parks nestled within the area, offering unforgettable entertainment and attractions for adults seeking fun and adventure.
  • Explore Local Wineries and Breweries: Discover the region's vibrant craft beverage scene by touring local wineries and breweries that showcase unique flavors and brewing techniques.
  • Golf at Top Courses: Enjoy a leisurely day on championship golf courses that provide scenic views and challenging play, perfect for golf enthusiasts visiting here.
  • Experience Nature at State Parks: Connect with the outdoors by exploring picturesque state parks that offer hiking, birdwatching, and serene landscapes just a short drive from your accommodations.

Other Places to Stay in Osceola County, FL

Kissimmee
Kissimmee Vacation Rentals
Disney's Maingate West
Disney's Maingate West Vacation Rentals
Four Corners
Four Corners Vacation Rentals
West Kissimmee
West Kissimmee Vacation Rentals
Historic Downtown Kissimmee
Historic Downtown Kissimmee Vacation Rentals
Reunion
Reunion Vacation Rentals
Windsor Hills
Windsor Hills Vacation Rentals
Disney's Maingate East
Disney's Maingate East Vacation Rentals
Windsor Palms
Windsor Palms Vacation Rentals
Bellavida
Bellavida Vacation Rentals
Lake Berkley
Lake Berkley Vacation Rentals
Buena Ventura Lakes
Buena Ventura Lakes Vacation Rentals
More Places to Stay Near Osceola County

Osceola County Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Adventure Early: To maximize your experience here, book your vacation rentals in advance to secure the best options and rates in this popular destination.
  • Explore Local Attractions: Take advantage of nearby parks and cultural sites to fully enjoy what this region uniquely offers without the hassle of long travel times.
  • Identify Prime Accommodation Locations: Choose vacation rentals close to major attractions or transportation hubs for convenience and more time to relax during your stay.
  • Immerse Yourself in the Local Environment: Engage with community events or try regional cuisine to enrich your visit to this vibrant destination within the area.

Transportation Options

  • Osceola County Airport (Polk County Airport): You can conveniently access this regional airport, offering domestic flights that make traveling to the area straightforward.
  • Walt Disney World Bus Service: This reliable transportation option connects you directly to many popular attractions and resorts within the region.
  • Rental Car Services: Numerous rental car agencies are available locally, providing flexible mobility options to explore the entire area at your own pace.
  • Public Transit - LYNX Bus Service: The area's public bus system offers an affordable way to navigate here and reach key destinations around Osceola County.

Local Customs Options

  • Southern Hospitality: Visitors often experience the region's warm and welcoming attitude, reflecting its friendly community and relaxed atmosphere.
  • You can enjoy regional culinary traditions that highlight fresh, local ingredients, showcasing the area's unique flavor profile.
  • Celebration of Nature: Respect for the natural environment is evident through outdoor customs and community events celebrating the area's diverse ecosystems.
  • Community Festivals: Engaging in local festivals provides insight into the area's vibrant culture and deep-rooted traditions that residents cherish.

Frequently Asked Questions About Osceola County?

1. What are the top vacation rentals 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 Vacation Rentals in Osceola County:

2. How many vacation rentals have private pools in Osceola County?

There are 19780 vacation rentals with private pools near Osceola County. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Osceola County are best for families?

If you are looking for a family-friendly vacation home in Osceola County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Osceola County:

4. How many Rentbyowner vacation rentals are available in Osceola County?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 41675 in the Osceola County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Osceola County. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by property, so you should review the specific listing for details. Some rentals offer flexible options, while others may have strict terms. It's best to contact the owner directly if you need clarification.

6. How do I find available dates and book my stay in the region?

You can easily check real-time availability and make a reservation through the listing’s booking system. Ensure your preferred dates are open before completing the process, and reach out to the owner if you have any special requests.

7. Are there any additional fees or charges when booking through this platform?

Additional fees such as cleaning, service charges, or taxes are typically outlined on the property’s listing page. Review all fee details carefully before confirming your booking to avoid surprises.

8. What amenities are typically included with vacation rentals in this destination?

Most properties come equipped with essential amenities like Wi-Fi, kitchen facilities, and parking. For specific features such as pools or pet accommodations, check the individual listing details or contact the host directly.

9. What should I know about check-in and check-out procedures for rentals here?

Check-in and check-out times are specified in each listing. Many hosts offer flexible arrangements, but it’s important to confirm these details beforehand to ensure a smooth arrival and departure process.

Osceola County Top Rated Vacation Rentals

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