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Discover Your Perfect Countryside Rentals by Owner

Countryside Rentals by Owner

10.0 (3 Reviews)
House
Welcome to Kissimmee!
  • Air Conditioner
  • Pool
  • Security/Safety
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More Top-Rated Rentals by Owner in Countryside Area

Why Choose Rent By Owner for your Countryside vacation rental?

What makes our Rentals by Owner 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 Countryside

When should you plan your Rentals by Owner stay?

Choosing the right time to vacation here can significantly enhance your experience, as the region offers ideal conditions for enjoying its attractions and amenities throughout the year.

Peak Season Highlights

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Spring (March to May)

During the spring months, this area experiences its peak season with warm weather and increased visitors seeking outdoor activities and local events. Booking your rental here ensures you enjoy the vibrant atmosphere at its best.

Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
winter
Winter Holidays (December to February)

The winter holiday period attracts many travelers looking to escape colder climates, making it a lively time in the region. Securing a rental during this time offers festive surroundings and excellent weather conditions.

Average Temperature Daytime: 70-78°F - Nighttime: 50-60°F

Off-Season Highlights

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Summer (June to August)

In the summer months, the area tends to see fewer visitors due to higher temperatures and humidity. This is an ideal time to find more affordable rentals and enjoy a quieter stay at your own pace.

Average Temperature Daytime: 85-95°F - Nighttime: 70-75°F
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Fall (September to November)

As the crowds diminish in fall, this destination becomes less busy, offering a peaceful environment for your vacation. It’s a great time to book rentals with flexible options and enjoy mild weather.

Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F

Weekly Weather Forecast for Countryside

How to Book Your Countryside vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Countryside

More Top-Rated Rentals by Owner in Countryside Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 swimming pool to relax and unwind in the sunny Florida weather.
  • Take advantage of outdoor barbecue grills for delightful meal gatherings with family and friends.
  • Benefit from spacious patios or decks, perfect for outdoor dining or lounging during your stay.
  • Explore well-maintained landscaped yards that offer a scenic and peaceful environment.
  • Utilize available outdoor seating areas to enjoy the warm climate while reading or chatting.
  • Look for community or shared outdoor spaces that promote leisure and social activities.
  • Access tennis courts or other sports amenities to stay active during your vacation here.

Top Attractions Around Countryside

What attractions are nearby?

During your stay, you'll find a variety of outdoor activities and local attractions nearby, allowing you to enjoy the best of what this area has to offer without straying far from your rental by owner.

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Family Activities

  • Gatorland Orlando: Experience an engaging wildlife adventure where your family can observe and learn about Florida’s native creatures in this popular attraction near the countryside.
  • Wild Florida Airboats & Gator Park: Explore the scenic waterways on an airboat tour that offers an exciting way to see the region's lush landscapes and diverse wildlife from a unique perspective.
  • Fun Spot America Kissimmee: Enjoy a day of classic amusement park fun with rides and attractions suitable for all ages, conveniently located close by for family-friendly entertainment.
  • Kissimmee Lakefront Park: Relax or play along the lakefront with picnic areas, playgrounds, and walking paths, providing a serene outdoor experience perfect for families visiting the area.
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Adult Activities

  • Golfing at local courses: Enjoy a leisurely day on the greens at nearby golf courses, ideal for both beginners and seasoned players seeking a relaxing experience in this scenic region.
  • Shopping at local outlets: Explore the area’s diverse shopping outlets to find unique souvenirs and essentials, making it convenient to enjoy your stay without leaving the region.
  • Fine dining experiences: Indulge in the culinary offerings of nearby restaurants that showcase local flavors, perfect for savoring the region’s distinctive cuisine during your visit.
  • Nature walks and scenic parks: Take advantage of the peaceful parks and nature trails in the neighborhood to unwind amidst the natural beauty that characterizes here.

Countryside Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining and Shopping: Take advantage of the area’s local eateries and shops to authentically experience the region's flavor without venturing far from your rental.
  • Plan Your Day Trips: Use the convenient location as a base to visit nearby attractions and natural sites, making the most of your time in this welcoming destination.
  • Use Nearby Amenities: Maximize your stay by utilizing the community pools, parks, and recreational facilities available within your rental’s neighborhood or close by.
  • Respect the Neighborhood: Maintain a peaceful environment by adhering to local quiet hours and respecting the property rules during your stay here.

Transportation Options

  • Rental Car Services: Conveniently explore the region with rental cars from well-known providers, offering flexibility to visit local attractions and enjoy your stay at your own pace.
  • Shuttle Services: Reliable shuttle options connect you directly to key points in this area, ensuring comfortable travel without the hassle of driving yourself.
  • Public Transportation: Local bus routes provide an economical way to navigate around the region, making it easy to reach nearby destinations from your vacation rental.
  • Taxi and Ride-Sharing: Professional taxi and ride-sharing services offer quick, on-demand transportation for exploring the surroundings with ease and confidence.

Local Customs Options

  • Polite Greetings and Handshakes: In the area, friendly greetings like handshakes or warm smiles are customary when meeting locals in the countryside of Kissimmee, Florida.
  • Respect for Nature and Environment: You'll notice a strong emphasis on preserving the natural beauty, with residents often practicing eco-friendly habits in their daily routines.
  • Celebration of Local Festivals: Participating or observing local festivals is common here, showcasing regional traditions and community spirit throughout the region.
  • Casual Attire and Dress Code: Casual and comfortable clothing is typical when attending gatherings or visiting the area’s attractions, reflecting the laid-back lifestyle of this destination.

Frequently Asked Questions About Countryside Rentals by Owner

1. What are the top vacation rentals in Countryside?

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

2. How many Rentbyowner vacation rentals are available in Countryside?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 245 in the Countryside 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 Countryside. 

3. What is the cancellation policy for a rental by owner in this area?

Cancellation policies vary by listing, so it's important to review the specific terms on the rental's page or contact the owner directly to understand the refundable amount and timeframes.

4. How do I confirm my booking with a rental by owner here?

You can confirm your reservation through the booking platform by following the owner’s instructions, which typically include submitting payment and receiving a confirmation email with all details.

5. Are there any additional fees I should be aware of when booking a rental by owner in this region?

Additional fees such as cleaning fees, service charges, or local taxes may apply; these are detailed on the listing page, or you can inquire with the owner for clarification before booking.

6. What amenities are usually included in rentals by owner in this destination?

Most rentals by owner include essential amenities like Wi-Fi, kitchen facilities, and parking, but it’s best to check the specific listing for details on what is provided during your stay.

7. How can I communicate with the owner if I have questions before booking?

You can reach out to the owner directly through the messaging feature on the booking platform to ask any questions about the property, policies, or availability before completing your reservation.

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More Top-Rated Rentals by Owner in Countryside Area