Discover Your Perfect Historic Downtown Kissimmee Vacation Homes

Why Choose Rent By Owner for your Historic Downtown 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.

Best Times to Visit Historic Downtown Kissimmee

When should you plan your Vacation Rentals stay?

To make the most of your stay, consider planning your vacation during the shoulder seasons when the area offers delightful weather and fewer crowds, ensuring a more authentic and relaxed experience in this charming destination.

Peak Season Highlights

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Spring (March to May)

During spring, the area experiences warm, inviting weather perfect for exploring local attractions and outdoor activities. It's a lively time when visitors seek the region's vibrant atmosphere.

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

The winter months bring cooler temperatures but still mild enough for enjoyable daytime outings. This period is popular among travelers looking to escape colder climates while enjoying festive events in this destination.

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

Off-Season Highlights

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Summer (June to August)

Summertime in the region is characterized by higher temperatures and increased humidity, making it ideal for water-based activities and relaxing indoors during the hottest parts of the day.

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

Autumn offers milder weather with less crowded streets, providing a peaceful setting to enjoy the area's charm without the peak season bustle.

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

Weekly Weather Forecast for Historic Downtown Kissimmee

How to Book Your Historic Downtown 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 Historic Downtown Kissimmee

More Top-Rated Vacation Rentals in Historic Downtown 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 a private outdoor lounging area with comfortable seating for relaxing evenings.
  • Take advantage of a well-maintained swimming pool, perfect for cooling off after exploring the area.
  • Make use of outdoor dining spaces to savor meals while enjoying the pleasant weather.
  • Benefit from lush landscaped gardens that add to the charm and tranquility of your stay.
  • Utilize designated barbecue grills for outdoor cooking and social gatherings.
  • Access well-equipped patios or decks ideal for morning coffee or evening unwinding.
  • Experience secure parking facilities that keep your vehicle conveniently close during your visit to here.

Top Attractions Around Historic Downtown Kissimmee

What attractions are nearby?

Here, you can explore a variety of local attractions and activities that showcase the vibrant culture and lively atmosphere of this destination, making your stay in Kissimmee truly memorable.

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Family Activities

  • Historic Downtown Kissimmee Museum Tour: Explore the area's rich history through engaging exhibits and preserved landmarks that bring the region’s past to life for the whole family.
  • Lakefront Park Activities: Enjoy scenic views and family-friendly recreation at this popular park, offering picnic areas, playgrounds, and gentle waterside walks perfect for a relaxing day.
  • Shopping and Dining in Downtown Kissimmee: Discover unique local shops and casual eateries that provide a taste of the region’s vibrant culture and flavor, ideal for families seeking a laid-back experience.
  • Historical Walking Tours: Take an informative stroll around the district’s historic sites and charming streets, providing both education and entertainment for visitors of all ages.
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Adult Activities

  • Explore the Historic Downtown Kissimmee Arts District: Discover local art galleries and vibrant murals that showcase the area's creative spirit and cultural heritage.
  • Dine at Charmingly Local Restaurants: Indulge in diverse culinary options reflecting the region’s rich flavors, perfect for a relaxed evening out.
  • Attend Live Music and Events: Experience the lively atmosphere at frequent concerts and festivals held in the heart of this destination.
  • Visit Unique Boutique Shops: Shop for handcrafted souvenirs and eclectic finds that capture the essence of the area's history and style.

Other Places to Stay in Historic Downtown Kissimmee, FL

Kissimmee
Kissimmee Vacation Rentals
AMF Bowling Center
AMF Bowling Center Vacation Rentals
Florida Technical College
Florida Technical College Vacation Rentals
Osceola Square Mall
Osceola Square Mall Vacation Rentals
Skate Reflections
Skate Reflections Vacation Rentals
Kissimmee Air Museum
Kissimmee Air Museum Vacation Rentals
Kissimmee Golf Club
Kissimmee Golf Club Vacation Rentals
Osceola County Clerk of the Court
Osceola County Clerk of the Court Vacation Rentals
Osceola Regional Medical Center
Osceola Regional Medical Center Vacation Rentals
First United Methodist Church
First United Methodist Church Vacation Rentals
Lanier's Historic Downtown Marketplace
Lanier's Historic Downtown Marketplace Vacation Rentals
Kissimmee Civic Center
Kissimmee Civic Center Vacation Rentals
More Places to Stay Near Historic Downtown Kissimmee

Historic Downtown Kissimmee Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Eateries: Take advantage of the area's vibrant culinary scene by sampling the diverse range of local restaurants and cafes, ensuring you experience authentic flavors during your stay.
  • Visit Historic Sites: Dive into the region's rich history by visiting key historic landmarks and districts right in the heart of this destination to gain a deeper appreciation of its cultural heritage.
  • Plan Your Transportation: Utilize nearby public transportation options or consider renting a bike or car to effortlessly explore the surrounding attractions and hidden gems in here.
  • Book in Advance: Secure your preferred vacation rentals early to enjoy the best locations and amenities, making your visit comfortable and stress-free in this popular area.

Transportation Options

  • Local Bus Services: Convenient for exploring the area and reaching key attractions, with regular routes connecting the neighborhood to surrounding regions.
  • Rideshare Options: Easy to book via mobile apps, providing quick and reliable transportation throughout this destination’s vibrant streets.
  • Rental Cars: Ideal if you prefer flexibility, allowing you to explore beyond the immediate vicinity at your own pace.
  • Taxi Services: Readily available for direct trips within the region, offering comfort and convenience during your stay.

Local Customs Options

  • Southern Hospitality: Embrace the friendly and welcoming nature that defines the area, where locals often greet visitors with warm smiles and open arms.
  • Family-Oriented Celebrations: Participate in lively local events and festivals that highlight the region’s strong sense of community and tradition.
  • Historic Preservation: Respect the area's rich history by observing local customs that honor its historic architecture and cultural heritage.
  • Local Cuisine Appreciation: Sample traditional Floridian dishes that reflect the unique flavors and culinary traditions rooted in this destination.

Frequently Asked Questions About Historic Downtown Kissimmee?

1. What are the top vacation rentals in Historic Downtown Kissimmee?

There are a lot of options in Historic Downtown Kissimmee. If you plan on staying in the Historic Downtown 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 Historic Downtown Kissimmee:

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

There are 5412 vacation rentals with private pools near Historic Downtown Kissimmee. Top-rated RBO homes that have access to a swimming pool include:

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

If you are looking for a family-friendly vacation home in Historic Downtown 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 Historic Downtown Kissimmee:

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 12850 in the Historic Downtown 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 Historic Downtown Kissimmee. 

5. What is the cancellation policy for vacation rentals in Historic Downtown Kissimmee?

The cancellation policy varies depending on the individual property owner. To ensure you understand the specifics, please review the cancellation terms listed on the property’s page or contact the host directly before completing your booking.

6. How do I find available dates for vacation rentals in this area?

Availability can be checked by using the search feature on the listing page, where you can enter your preferred dates. Always confirm with the host if you have specific scheduling needs or questions about reservation availability.

7. Are there any additional fees associated with booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or local taxes are typically detailed in the listing. It’s recommended to review these details carefully and reach out to the property owner if you need clarification.

8. What amenities are usually included in vacation rentals in the region?

Most properties offer amenities like Wi-Fi, air conditioning, fully equipped kitchens, and laundry facilities. To ensure the rental meets your needs, consult the detailed amenities list provided on each listing.

9. How can I communicate with the property owner during my stay?

Communication is facilitated through the messaging system on the booking platform. You can contact the owner anytime before and during your stay for questions or assistance, ensuring a smooth experience from reservation to check-out.

Historic Downtown Kissimmee Top Rated Vacation Rentals

See More Historic Downtown Kissimmee Vacation Rentals