living room in our Kissimmee vacation homes

Situated in the heart of Osceola County in Central Florida is a destination that’s bound to inspire travelers from near and far. Kissimmee is a place where travelers are encouraged to kick back and relax while focusing on the fun instead of the demands of daily life for a while. Year-round Kissimmee offers up a great space to settle into comfort and style or get out and explore as well. Brimming over with shopping and dining opportunities of its own, Kissimmee comes with the added benefit of keeping travelers close to some of the most notorious Central Florida landmarks they don’t want to miss out on while they’re in town. Home to Lake Tohopekaliga, Kissimmee is a vacation destination where visitors can pair land-based fun with options to get out on the water too. There are plenty of nature parks to enjoy here and a trip this way is a chance to savor each and every moment. At Casiola Orlando, we know that the only way to elevate a stay in Kissimmee even further is to have amazing vacation rental accommodations lined up that keep you close to the fun and living in impeccable style. Our collection of Kissimmee vacation homes is designed with versatility in mind to suit travelers of all types and to not only meet every need but exceed our guest’s expectations too. All of our vacation homes offer guests access to world-class amenities as well as great views and extras that make all the difference in a getaway. At Casiola Orlando, we wouldn’t have it any other way!

Browse our Kissimmee Vacation Homes Below!

Make More of Every Kissimmee Moment

Kissimmee, Florida is a fantastic place for travelers to leave any and all thoughts of cold weather living behind in the name of endless year-round sunshine. The average daily temperature here lingers in the 80s while evenings see things dropping into the comfortable 60s. This means that no matter when you arrive in town or how long you plan to stay, outdoor fun can always be paired up with those inside adventures too. Of course, for guests who can’t wait to get out and explore, Kissimmee is refreshingly close to Walt Disney World and Universal Studios Florida as well. This locale is home to the Kissimmee Chain of Lakes for afternoons filled with fun paddling, kayaking, or fishing your way through a stay. Visitors who are looking to add some day trips to their itinerary will find Kissimmee puts them in the perfect place to easily access destinations like the Everglades, the Kennedy Space Center, or the Gulf of Mexico.

A true highlight of a getaway to Kissimmee for many travelers is often the opportunity to explore and enjoy Old Town. Here, you can find time to enjoy mind-bending adventures at The Great Magic Hall or embrace some friendly competition at the Happy Days Family Center. Old Town is packed with souvenir shops and eateries to explore while time riding the Ferris Wheel shouldn’t be missed.

Enjoy the Best of Kissimmee Vacation Living

A getaway to Kissimmee any time of year is already bound to be an inspiring experience for travelers. Those who have booked Kissimmee vacation homes through Casiola Orlando have even more to look forward to! No matter when you arrive, how long you plan to stay, or how many fellow adventurers you arrive alongside, our collection of Kissimmee vacation homes hosts the style, luxury, comfort, and conveniences you’ve been looking for. Whether you’re excited to get settled into a cozy abode or require a sprawling retreat for a family reunion, we have you covered. All of our property options work as a testament to world-class quality and offer up the space guests need to move easily between interior living spaces during their stay. When visitors have the room they need to relax and enjoy every moment, the getaway is bound to be that much more meaningful.

Stepping inside our Kissimmee vacation homes, guests will often find spacious open floor plans waiting to greet them. The square footage is further enhanced with vaulted ceilings in many of our property options too. Those rentals with large windows throughout come with the added benefit of allowing ample natural light flow to flood the space and a firm focus to be found on the view at all times too. The result is a bright, open, airy, and welcoming place to call your home away from home the next time you’re here. Guests will love how so many of our Kissimmee vacation homes have large bedrooms included where resting up in style is a breeze after a day of Florida fun. Tasteful and stylish furnishings are a staple in all of our vacation homes in Kissimmee, Florida as well and many collections perfectly pair home comforts with those Florida-inspired style elements that make a stay unforgettable. When our guests are looking to be able to customize their downtime, booking one of our Kissimmee vacation homes with Wi-Fi included is a must. When paired up with large flat-screen and smart televisions, visitors can personalize their digital entertainment at the touch of a button.

Elevate the Adventure with Luxury

Sometimes, there’s nothing more refreshing than getting out and enjoying dinner at a delightful restaurant with world-class service included. Other times, it’s a home-cooked meal that would really hit the spot. When the latter is what you’re craving during your time in Kissimmee, booking one of our rental homes with a fully equipped kitchen included makes all the difference. These culinary spaces provide easy access to spacious counters, custom cabinetry, high-end appliances, and cooking essentials that make serving breakfast, lunch, or dinner seamless! Most of our rental homes have large dining rooms included but guests can always choose to head out to furnished patios, porches, or decks to make the most of an al fresco meal during their stay instead.

For an even more luxurious getaway, simply ask about our ChampionsGate luxury rentals that come with fun extras. We’re happy to help guests get settled into property options that come with private hot tubs and pools as well as those with game rooms, media centers, custom-built bedrooms, and specific views too. Whether it’s a large yard that would make all the difference, or you’re looking for a kitchen with a large center island for more meal preparation convenience, we can help you find the home that checks every box on the list.

Book Our Kissimmee Vacation Rentals Today

Take time to unwind, relax, and enjoy the very best of a Kissimmee getaway when you’re overdue for a well-deserved vacation. Pamper yourself with a stay at our Kissimmee luxury rentals and elevate your vacation experience from start to finish. When you know that having incredible accommodations booked would help you make more of every moment, reserving your rental through Casiola Orlando is always the way to go. We know what it takes to elevate a great stay to the level of exceptional and unforgettable, that’s why we offer our guests the very best Kissimmee weekly rentals to stay in. Our team is happy to handle the logistics and details so that our guests can focus exclusively on the fun that awaits ahead. Take time to browse our many exciting and luxurious options across Kissimmee and when you land on the home you love, you can rest easy knowing booking a stay is as easy as the click of a button. There’s never been a better time to start turning those travel plans into a reality. At Casiola Orlando, we look forward to seeing you in sunny Florida soon!

Menu