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Kissimmee Luxury Rentals

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Kissimmee Pet Friendly Vacation Rentals

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10.0 (7 Reviews)
House
Mufasa's Pride
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Kissimmee Large Vacation Homes

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Why Choose Rent By Owner for your Kissimmee 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.

Popular Areas for Kissimmee Vacation Rentals

Where are the best neighborhoods to stay in Kissimmee?

When planning your trip to Kissimmee, Florida, choosing the right neighborhood can greatly enhance your vacation experience. Each area offers a unique atmosphere, whether you're seeking proximity to family-friendly attractions, convenient access to entertainment venues, or peaceful surroundings for relaxation. Exploring neighborhoods within Kissimmee allows you to find the perfect setting that matches your travel preferences, making your stay both comfortable and memorable. With a wide selection of dependable vacation rentals in prime locations, your ideal getaway is just a booking away.

West Kissimmee

This area offers a tranquil retreat with spacious vacation rentals, making it ideal for travelers seeking relaxation near Orlando’s major attractions. The region provides convenient access to theme parks while maintaining a peaceful atmosphere.

View 21716+ Rentals in West Kissimmee

Bay Lake

Nestled close to the heart of the region, Bay Lake is known for its scenic surroundings and proximity to some of the area's most popular attractions. Guests here enjoy easy access to vibrant entertainment options within a beautiful lakeside setting.

View 1254+ Rentals in Bay Lake

Historic Downtown Kissimmee

The historic district exudes charm with its quaint streets and cultural appeal, offering a unique stay experience in the midst of local history. It’s perfect for those who want to explore authentic Florida heritage while enjoying modern conveniences.

View 10885+ Rentals in Historic Downtown Kissimmee

Windsor Hills

Known for its family-friendly atmosphere, Windsor Hills features well-equipped vacation homes in a secure community. It’s an excellent choice for convenience and comfort, with easy access to nearby theme parks and family activities.

View 2119+ Rentals in Windsor Hills

Orange Lake

Surrounded by lush landscapes, Orange Lake offers a relaxing environment with amenities geared toward outdoor recreation. Its location makes it a prime spot for visitors seeking both adventure and leisure.

View 131+ Rentals in Orange Lake

Lake Berkley

This neighborhood boasts serene lakeside views and spacious vacation homes, ideal for guests looking for a peaceful escape. The area’s natural beauty complements its close proximity to local attractions.

View 200+ Rentals in Lake Berkley

Windsor Palms

Popular among travelers seeking a resort-style experience, Windsor Palms offers a variety of well-appointed vacation properties with excellent community amenities. It’s a perfect base for exploring the region’s top destinations.

View 1220+ Rentals in Windsor Palms

Bellavida

Bellavida features a gated community with luxurious vacation rentals set amidst lush landscaping. Visitors appreciate its prime location and the serene environment for a memorable stay.

View 341+ Rentals in Bellavida

Best Times to Visit Kissimmee

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can greatly enhance your experience, as the region offers different attractions and weather patterns depending on the season, making it essential to plan your stay accordingly for a memorable getaway.

Peak Season Highlights

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Spring (March to May)

During spring, the area experiences warm weather and lively local events, making it an ideal time to enjoy your vacation rental in this destination.

Average Temperature Daytime: around 80°F - Nighttime: about 60°F
winter
Winter Holidays (December to February)

The winter months bring cooler temperatures and festive celebrations, providing a charming setting for your stay in this region.

Average Temperature Daytime: approximately 70°F - Nighttime: around 50°F

Off-Season Highlights

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Summer (June to August)

Summertime in the area features hot temperatures and lighter crowds, offering excellent opportunities for budget-friendly stays at your preferred vacation rentals.

Average Temperature Daytime: around 90°F - Nighttime: about 70°F
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Fall (September to November)

Autumn brings mild weather and fewer visitors, creating a peaceful atmosphere for exploring and relaxing at your vacation rental in this destination.

Average Temperature Daytime: around 75°F - Nighttime: about 55°F

Weekly Weather Forecast for Kissimmee

How to Book Your Kissimmee 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 Kissimmee

More Top-Rated Vacation Rentals in Kissimmee 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 outdoor swimming pools available at many properties, perfect for relaxing after a day of exploring the region.
  • Make use of private or shared patios and decks to unwind and soak up the sunny Floridian weather.
  • Take advantage of well-maintained outdoor grilling areas for family barbecues in the warm climate.
  • Benefit from lush landscaped gardens and scenic courtyards that provide tranquil environments for your stay.
  • Participate in outdoor sports facilities such as tennis courts and basketball courts often available on-site.
  • Relax in outdoor lounge areas designed for socializing or enjoying the evening air in this popular destination.
  • Utilize spacious yards and lawns, ideal for outdoor activities or simply soaking up the sunshine here in the region.

Top Attractions Around Kissimmee

What attractions are nearby?

Within this vibrant region, you can enjoy a variety of activities nearby, from exploring world-class theme parks to engaging in outdoor adventures, making it an ideal destination for your next vacation rental stay.

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Family Activities

  • Disney's Animal Kingdom Theme Park: You can explore this iconic Disney park to see exotic animals and enjoy immersive rides, making it a favorite family activity here.
  • Old Town Kissimmee: Stroll through this lively area with classic car shows, family-friendly shops, and casual dining options, perfect for spending quality time together in the region.
  • Kissimmee Lakefront Park: Relax and have fun at this scenic lakeside park featuring playgrounds, picnic areas, and paddle boat rentals, ideal for outdoor family outings.
  • Celebration Town Center: Discover this charming community with entertainment, shopping, and food options that cater to families looking for a relaxed day out nearby here.
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Adult Activities

  • Walt Disney World Resort: Immerse yourself in world-renowned entertainment and attractions at this iconic destination, just a short drive from your Kissimmee vacation rental.
  • Old Town Shopping and Entertainment District: Experience lively shopping, dining, and live entertainment that captures the vibrant spirit of the region’s nightlife and local culture.
  • Gatorland: Encounter Florida's native wildlife up close with thrilling shows and exhibits that showcase the area's unique natural heritage.
  • Shopping at Osceola Square Mall: Indulge in retail therapy and find great deals at this popular shopping center near your vacation rental here in the region.

Other Places to Stay in Kissimmee, FL

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
Lindfields
Lindfields Vacation Rentals
More Places to Stay Near Kissimmee

Kissimmee Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During Off-Peak Seasons: Visiting during less busy times allows you to enjoy a more relaxed experience and better deals on local attractions and accommodations.
  • Utilize Local Transportation Options: Taking advantage of public transit or rental cars can help you explore the region conveniently and affordably, maximizing your time here.
  • Choose a Strategic Location for Your Stay: Booking nearby popular attractions ensures easier access to the area's highlights and reduces travel time during your trip.
  • Explore the Area’s Dining and Entertainment Choices: Sampling local eateries and entertainment venues enhances your visit and provides authentic experiences in this destination.

Transportation Options

  • Shuttle Services: Reliable shuttle services are available to and from the area's major attractions, making transportation convenient for travelers staying in local vacation rentals.
  • Rental Cars: Renting a car offers you the flexibility to explore the region at your own pace while staying comfortably close to your chosen vacation rental property.
  • Public Buses: The local bus system provides an affordable way to navigate the region and reach key destinations near your vacation rental in this popular destination.
  • Taxis and Ride-Sharing: Taxis and ride-sharing services like Uber and Lyft operate throughout here, providing quick, dependable transportation right to your vacation rental doorstep.

Local Customs Options

  • Southern Hospitality: You’ll notice a warm and friendly attitude in the area, reflecting the region's famous southern hospitality that welcomes visitors with open arms.
  • When enjoying local cuisine, it’s customary to be polite and patient, as this destination values courteous interactions and shared community experiences.
  • Festive Celebrations: Participating in seasonal festivals and events is common here, showcasing the area’s vibrant culture and love for spirited gatherings.
  • Respect for Nature: The region emphasizes environmental conservation, so you are encouraged to respect local parks and natural sites during your stay.

Frequently Asked Questions About Kissimmee?

1. What are the top vacation rentals in Kissimmee?

There are a lot of options in Kissimmee. If you plan on staying in the Kissimmee area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Kissimmee:

2. How many vacation rentals have private pools in Kissimmee?

There are 20430 vacation rentals with private pools near Kissimmee. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Kissimmee are best for families?

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

4. How many Rentbyowner vacation rentals are available in Kissimmee?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 43114 in the Kissimmee 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 Kissimmee. 

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

Cancellation policies vary depending on the property listing. You should review the specific cancellation terms outlined in the rental agreement or contact the property owner directly to understand the options and any applicable fees.

6. Are there any age requirements or restrictions when booking a vacation rental here?

Age restrictions can differ between properties. It’s best to check the listing details or speak with the property owner to ensure your group meets any age-related policies before booking.

7. How do I find vacation rentals that allow pets in this destination?

Pet-friendly options are available but vary by property. Use the search filters on the booking site to specify pet policies, and always confirm with the host about any additional fees or rules regarding animals.

8. What amenities are typically included in vacation rentals in this part of Florida?

Many rentals offer amenities such as private pools, full kitchens, Wi-Fi, and outdoor spaces. To see what’s available, review the property description and amenities list on each listing or contact the owner for further details.

9. How can I confirm the availability of a specific vacation rental during my preferred travel dates?

Availability can change quickly, so it’s recommended to check real-time calendar updates on the listing. If you have questions, reaching out directly to the owner ensures you receive the most current information.

Kissimmee Top Rated Vacation Rentals

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