When you can’t wait to leave the hustle and bustle of daily life behind and focus on the fun for a while instead alongside family and friends, there’s no better place to book a vacation than Kissimmee, Florida. Situated in the heart of Osceola County, Kissimmee sits south of Orlando and all of the vast activities, attractions, and landmarks that await to be explored. Of course, choosing to stay in Kissimmee means easy access to area fun as well as the city sits on the shores of Lake Tohopekaliga and is packed with shops, restaurants, trails, and entertainment venues to check out during your visit. Whether you’re looking to enjoy a few days away or you’re lucky enough to make the most of an extended getaway, you can elevate your Kissimmee experience even further by booking accommodations through Casiola Orlando. Our collection of Kissimmee vacation rentals keeps visitors close to the fun they can’t wait to experience for themselves while savoring amazing amenities, and top-notch features too. Our Kissimmee vacation rentals come in all shapes, styles, and sizes to accommodate travelers of all types. Whether you’re looking for a cozy abode for two or you’re excited to enjoy a family reunion in Florida, our vacation rentals offer up the space, luxury, and views to take every getaway up a notch. At Casiola Orlando, we wouldn’t have it any other way for our guests!
Kissimmee Vacation Rentals
Browse our Kissimmee Vacation Rentals Below!
Spacious, Family-Friendly Pool Home w/Game Room in Solara
House - Solara Resort - Orlando
Modern Townhome w/ Pool+ Spa | Game Room | BBQ
Townhome - ChampionsGate Resort - Orlando
Beautifully Decorated 9 BR Pool Home w/Spa + Game Room!
House - ChampionsGate Resort - Orlando
9BR/5BA Pool Home at ChampionsGate Resort *Sleeps 23*
House - ChampionsGate Resort - Orlando
Private Pool + Spa * Game Room * near Clubhouse
House - Solara Resort - Orlando
5 of 262 properties
Enjoy Every Moment in Kissimmee
Travelers who take time to book a Kissimmee vacation rental through Casiola Orlando will find they have easy access to all of the best features the city offers up freely. Kissimmee is known and loved for its year-round amazing weather with highs averaging 82 degrees Fahrenheit and lows lingering around 62 degrees. This means that you never have to worry about not being able to enjoy the outdoor fun and adventure ahead. Feel free to leave the coats behind at home and savor time under the sun here instead. Kissimmee is an extremely welcoming and inviting community where residents and locals alike will find they enjoy spending time in the same locales. A stay here is a chance to make the most of easy access to world-class attractions and theme parks like Universal Studios Florida and Walt Disney World too. Check out our Orlando house rentals near Disney for a convenient stay! It doesn’t take long to drive from Kissimmee to nearby iconic stops such as the Gulf of Mexico, the Everglades, and the Kennedy Space Center. If spending time immersed in the beauty of nature is your vacation style, Kissimmee is a prime place to access amazing nature parks. The Kissimmee Chain of Lakes is ideal for fishing and boating alike while Lake Tohopekaliga is brimming over with bass and is great for paddleboarding too.
When you book a stay in a Kissimmee vacation rental through Casiola Orlando, there are also endless opportunities to explore the best of Kissimmee Old Town. This district is family-friendly and packed with opportunities for entertainment and attractions that are suitable for interests of all types. Old Town is a destination where visitors can regularly attend classic car shows and live musical events. It’s also a great place to explore places like The Great Magic Hall, and a Ferris Wheel, and make the most of interactive adventures at the Happy Days Family Fun Center. Pizza and hot dog stops are easily found in Old Town which is also home to a variety of unique souvenir shops whether you’re looking for something to remember your trip by, or excited to pick up something for a loved one back home.
Amenities Designed to Inspire
At Casiola Orlando, our portfolio of Kissimmee vacation rental property options fits every taste, preference, and travel style. Guests can enjoy settling into a modern retreat or opt for a rustic-chic aesthetic if they choose. No matter what property option our guests select, they’ll find that all of our Kissimmee vacation rentals work as a testament to the quality, comfort, and impeccable style standards too. Our team knows that having the space you need to relax and roam at will during a stay makes all the difference. That’s why guests will find so many of our Kissimmee vacation rentals are designed as open-concept floor plans. This makes it easy for guests to move seamlessly between living, sleeping, entertainment, dining, and lounge areas during their stay, no matter how many fellow travelers they arrive alongside. These floor plans are also typically paired up with large windows throughout as well as tall ceilings too. This combination further enhances the overall sense of living space available while putting a firm focus on the view and promoting the best natural light flow. The result? A bright, airy, and stylish place for guests to call their home away from home in Kissimmee starting the day they arrive in town.
Inside, all of our vacation rentals in Kissimmee host an inviting collection of stylish and comfortable furnishings too. Many collections capture the best of Florida-inspired style and pair it up with those home comforts our guests crave. Collections can include everything from plush sofas and loveseats to stylish accent chairs, area rugs, wall art, lighting, charming coffee tables, and end tables too. When it comes time to customize digital entertainment options, be sure to ask about our Kissimmee vacation rentals that are set up with Wi-Fi included as well as large flat-screen and even smart televisions throughout. After a day of fun in the sun across Kissimmee and Orlando, guests can rest up in style in the large bedrooms found in our Kissimmee weekly rentals. Many host spacious bedroom sets topped with cozy mattresses, high-quality linens, and stylish comforters.
Make More of Your Getaway
Kissimmee is packed with savor stops to enjoy during a visit this way, but those who find themselves longing for a home-cooked meal during their travels can have that too when they book one of our Kissimmee vacation rentals with a full kitchen included. These culinary spaces inspire guests to put their best chef skills to the test. Many host everything needed to serve up savory breakfast, lunch, or dinner options including spacious counters, custom cabinetry, dishes, utensils, cooking essentials, and high-end appliances. When it’s time to enjoy a meal, gather around large interior dining room tables or head out to furnished patios, porches, and decks where an al fresco meal with a great view is an option too. Looking for more in the way of luxury? Be sure to ask about our rentals that come with private pools and hot tubs as well as those with game rooms, specific views, and custom-built master suites!
Book Your Stay at the Best Kissimmee Vacation Rentals
Make more of every moment in Kissimmee, Florida when you book one of our inviting, spacious, and stylish Kissimmee luxury rentals the next time travel plans bring you this way. We’re happy to handle details so that you can focus exclusively on the well-deserved fun ahead. Take time to browse our wide variety of fantastic property options in the area and enjoy knowing that when you land on the one you love most, it’s no more than the click of a button away! Don’t miss out on our last-minute deals! There’s never been a better time to enjoy a vacation this way and our team is looking forward to seeing you in sunny Kissimmee soon.