Destination guide

No need to kiss and tell—Kissimmee is wholesome fun

Set just south of Orlando in Florida's Osceola County, Kissimmee's population has doubled twice since Walt Disney World opened nearby in 1971. Once a rural outpost where citrus groves and cattle ranches flourished, the city has maintained a sense of the past with a historic downtown, antique shops, and vintage amusement parks. Its sunny weather and wetlands make it a destination for anyone seeking warm temps, whether you prefer a weekend relaxing poolside or a more vigorous outdoor adventure. Its family attractions and close proximity to Disney make it a draw for the young and the young-at-heart.

Activities

Kiss boredom goodbye as you zipline past Florida wildlife

Kissimmee's historic downtown is the center of commercial life and offers a mix of family-owned businesses, shops, and restaurants. Consider a Kissimmee vacation rental within walking distance of Main Street, where you can enjoy breakfast at an outdoor cafe before deciding how you'll take in the surrounding wetland wilderness. Eco-tours via horseback, zipline, or airboat are just a few of your options. You'll likely have the chance to spot alligators, black bears, and dozens of bird species. Nighttime helicopter tours over the city provide a unique thrill, as the region's theme park lights twinkle below.

Weather

Sun-kissed weather year-round in Kissimmee

You don't have to worry about the cold in Kissimmee, even in winter. January temperatures average in the 70s, and skies are typically sunny. The city is crowded during the Christmas holiday but otherwise peaceful, and you might score a Kissimmee vacation rental at a low rate. Spring weather is mild, with highs between the 60s and 80s, and rental prices are still low. Summer is the busy season and also the hottest, so look for lodging with air-conditioning. Temperature-wise, autumn is as lovely as spring, but it's also the height of hurricane season, so check local forecasts.

Natural features

Blow a kiss to a bald eagle from your Kissimmee kayak

Set on the headwaters of the Everglades, the largest subtropical wilderness in the U.S., and on the northern border of Lake Tohopekaliga, your Kissimmee vacation rental is surrounded by wetlands and animal habitats. Many of these are protected in Nature Conservancy's Disney Wilderness Preserve, 15 miles south of Kissimmee. It's an 11,500-acre home to gopher tortoises, bald eagles, and sandhill cranes. The Shingle Creek Regional Park is another natural wonder, this one right in the city itself, with rivers for kayaking and canoeing, and nature trails for spotting birds.

How to get there

Transportation to and around Kissimmee

The nearest airport is in Kissimmee, FL (ISM-Kissimmee Gateway), located 1.9 mi (3 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Orlando, FL (MCO-Orlando Intl.), which is 11.2 mi (18 km) away.

If you're traveling by train, the main station serving the city is Kissimmee Station.

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:

  • Terra Verde Resort: 1,720 vacation rentals
  • Reunion: 8,967 vacation rentals
  • Lake Berkley: 1,521 vacation rentals
  • Bellavida: 1,567 vacation rentals
  • Trafalgar Village: 71 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:

  • Kissimmee Lakefront Park: 35,969 vacation rentals
  • Reunion Resort Golf Course: 40,832 vacation rentals
  • Old Town: 40,956 vacation rentals
  • Silver Spurs Arena: 39,995 vacation rentals
  • Kissimmee Civic Center: 40,874 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 11,747 Houses in Kissimmee. Our other popular types of vacation rentals in Kissimmee include:

  • Villas: 15,172 rentals available
  • Condos/Apartments: 4,050 rentals available
  • Townhouses: 7,738 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 preferred vacation rental with pool among our 37,388 vacation rentals with pool available in Kissimmee. Please use our search bar to access the selection of vacation rentals available.

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