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Kissimmee vacation homes for your perfect getaway

Trusted by over 16,115 guests · Save 15% on platform fees · Secured by Stripe

About This Collection

As the vibrant colors of fall begin to grace Kissimmee, Florida, the city transforms into a haven for family getaways. With its close proximity to world-renowned theme parks and natural attractions, Kissimmee offers a unique blend of adventure and relaxation. This season, families can take advantage of the mild weather, making it an ideal time to explore outdoor activities, enjoy scenic parks, and experience the magic of nearby attractions without the summer crowds.

Our collection of entire homes in Kissimmee is perfect for families seeking a comfortable and spacious retreat. With amenities designed for relaxation and fun, such as pools and game rooms, these properties cater to both adults and kids alike. To make the most of your stay, consider planning a day at the local parks followed by a cozy family movie night in your rental. This fall, create unforgettable memories in Kissimmee, where every moment is a chance to bond and enjoy the magic of family time.

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What Our Guests Have To Say

Don't take our word for it - trust the 16115 reviews from our guests.

Jieun Moon
We didn’t get a Mountain View, but that was alright because the property was beautiful. The swimming pools were heating with a variety of hot tubs. It honestly was amazing! Our four year old son spent 4 hours in the heated pool. The staff is amazing and friendly, and everything was very clean.

Jieun Moon

5
·

Oct 2025

Other Properties

Frequently Asked Questions

Gain expert insights on finding and booking the best vacation rentals in Kissimmee for your family getaway.

When searching for a family-friendly rental in Kissimmee, prioritize homes with multiple bedrooms, spacious living areas, and kid-friendly amenities like pools or game rooms. Proximity to attractions such as Disney World is also a key factor, ensuring easy access to entertainment. Consider properties with safety features like pool fences and childproof locks for peace of mind.

The best time to visit Kissimmee is during the spring and fall months when the weather is pleasant and crowds are thinner. Summer can be hot and humid, attracting more families due to school vacations. If you're looking to avoid peak pricing, consider visiting in early September after the summer rush.

Vacation rentals in Kissimmee often provide more space, privacy, and amenities like kitchens and private pools, making them ideal for families or groups. Unlike hotels, rentals allow for a home-like environment, which can enhance your overall experience. Additionally, having a full kitchen can help save on dining costs during your stay.

A good pool home rental in Kissimmee should have a well-maintained pool area, safety features like alarms or fencing, and comfortable outdoor furniture for relaxation. Look for properties that offer sun exposure throughout the day and shaded areas for breaks from the heat. Proximity to attractions can also enhance your poolside experience after a day of exploring.

When renting a vacation home in Kissimmee, familiarize yourself with local regulations regarding short-term rentals and community rules. It's also important to consider the amenities that will best suit your group’s needs, such as laundry facilities or accessibility features. Understanding the peak tourist seasons can help you plan your visit for the best experience.

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