Explore
Find the perfect place from the worlds best selection of vacation rentals on VRBO.
Where to stay around Kissimmee, FL?
Our 2018 property listings offer a large selection of 36,637 vacation rentals near Kissimmee. From 13,307 Houses to 11,253 Villas, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Kissimmee for a holiday or a weekend are on VRBO.
What is the best area to stay when traveling to Kissimmee?
Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Kissimmee:
- Reunion: 8,123 vacation rentals
- Terra Verde Resort: 1,729 vacation rentals
- Cumbrian Lakes: 240 vacation rentals
- Lake Berkley: 1,524 vacation rentals
- Venetian Bay Villages: 397 vacation rentals
For other neighborhoods, please use our search bar to access the selection of vacation rentals available.
What are the popular point of interests near where I can stay when traveling to Kissimmee?
VRBO offers a large selection of vacation rentals near lovely places in Kissimmee. From VRBO travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:
- Osceola County Stadium: 38,232 vacation rentals
- Gaylord Palms Resort & Convention Center: 21,808 vacation rentals
- Reunion Resort Golf Course: 39,453 vacation rentals
- Kissimmee Lakefront Park: 36,692 vacation rentals
- Old Town: 39,697 vacation rentals
But there are many other points of interest around Kissimmee listed on VRBO where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.
Can I rent Houses in Kissimmee?
Yes, of course. VRBO has 13,307 Houses in Kissimmee. Our other popular types of vacation rentals in Kissimmee include:
- Villas: 11,253 rentals available
- Townhouses: 5,800 rentals available
- Condos/Apartments: 4,244 rentals available
But you can also enjoy a great stay in one of our other vacation rentals including Resorts and more.
Can I find a vacation rental with pool in Kissimmee?
Yes, you can select your prefered vacation rental with pool among our 34,020 vacation rentals with pool available in Kissimmee. Please use our search bar to access the selection of vacation rentals available.
Kissimmee—Florida’s favorite family playground
Fun-filled vacations come as standard in Kissimmee, central Florida’s sun-kissed family playground. This friendly city has much to offer in its own right, while proximity to some of the state’s biggest visitor attractions creates a year-round demand for Kissimmee vacation rentals. Heritage and nature go hand in hand in this historic community on the scenic shores of Lake Tohopekaliga. From the classic American entertainment of Old Town to the rich wildlife of Makinson Island, Kissimmee vacation rentals offer the perfect combination of laid-back relaxation and stimulating activity, with Florida’s benevolent climate adding the finishing touch.
A step back in time in downtown Kissimmee
Kissimmee’s early prosperity was built around its shipyard, which supported the thriving steamboat trade along the Kissimmee River. Many buildings from this era can still be admired on a leisurely stroll through the Historic Downtown district, past stunning family mansions and the quaint stores and traditional diners of Main Street. Kissimmee Lakefront Park promises a tranquil extension to your walk and a chance to enjoy panoramic views of Lake Tohopekaliga. The fishing pier, picnic pavilions, and playground are popular meeting spots, while jogging and cycling trails offer the chance to let off steam in the cool lakeside air.
Heritage highlights in Kissimmee
The Osceola County Welcome Center and History Museum delivers living history before your very eyes. The museum has recreated a traditional pioneer village from authentic structures carefully relocated from around the county. Highlights include cattle ranchers’ homesteads, a blacksmith’s shop, and a replica train depot. Another view of old America can be experienced at Old Town theme park, which replicates the style of a classic Floridian town. Kissimmee vacation rentals near Walt Disney World® Resort offer the chance to contrast the old-fashioned charms of historic Florida with the contemporary thrills of the latest rides.
Kissimmee—a warm welcome guaranteed
No prizes for guessing the main feature of Kissimmee’s weather—central Florida’s humid subtropical climate guarantees a warm welcome whatever the season. Long, hot summers and reliably mild winters mean there’s no let-up in demand for Kissimmee vacation rentals, so early booking is recommended to be sure of the best availability. Humidity peaks in the hottest months of July and August, so Kissimmee vacation rentals with a pool usually get snapped up first. If you find yourself succumbing to the refreshing pull of the ocean, the balmy waves of the Atlantic are just 65 miles away.
Kissimmee’s wild side
Makinson Island is a protected conservation area in Lake Tohopekaliga, with a circular trail that offers up-close views of the region’s indigenous wildlife. Alligators, herons, and river otters are just some of the creatures that live on this unspoiled island, which is only accessible by private craft. The nearby Disney Wilderness Preserve stretches along the shoreline of Lake Russell and provides a natural habitat for over 1,000 species of plants and animals. These headwaters of the Everglades support many varieties of water birds, while the preserve is also home to wild turkeys and sandhill cranes.