Destination guide

Kissimmee vacation rentals offer a mix of leisure and adventure

If you're thinking about spending a holiday in Florida, you can bet Kissimmee is one of the best places to visit. It's been a holiday hotspot for decades, renowned for its sunshine and Southern hospitality. The addition of nearby world-famous theme parks in Orlando have turned the city into a launchpad to visit sites like Disney's Hollywood Studios and Universal Parks & Resorts. By staying in Kissimmee, you get the bonus of maintaining some distance from larger crowds. You'll find thousands of sleek villas with luxurious views and even more vacation home rentals that are perfect for the whole family.


The name Kissimmee is shared with the river that flows through south-central Florida, and is debated to have stemmed from Native American origins. The town area was known as Allendale for a period of time, dedicated to a Confederate major who operated the first steamboat along the river. It was renamed Kissimmee after city incorporation in 1883. History buffs and military enthusiasts can get a kick out of the Museum of Military History, which details the past century of the American military experience. Many other historical sites and museums accessible from your vacation rental await in Kissimmee.


Sightseeing in and around Kissimmee

Are you hoping to find things to do while you're in the area? Venture out of your vacation home and experience everything that makes Kissimmee a one-of-a-kind vacation spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • SeaWorld® Orlando (8.9 mi / 14.3 km)
  • Universal Studios Florida™ (12.8 mi / 20.5 km)
  • Walt Disney World® (13.6 mi / 21.9 km)
  • Gatorland® (3.8 mi / 6.2 km)
  • Discovery Cove (8.4 mi / 13.6 km)
  • Aquatica (8.9 mi / 14.3 km)

Seasonal weather averages in Kissimmee

If you're hoping to enjoy some warm-weather activities on your vacation, July, August, June and September are the hottest months to visit, when temperatures average 91°F.

Natural features

Exploring the natural landscape of Kissimmee

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Kissimmee is a great place to get outside. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Kissimmee Lakefront Park (0.2 mi / 0.4 km)
  • Brinson Park (0.5 mi / 0.8 km)
  • Shingle Creek Regional Park (3 mi / 4.8 km)
  • Lake Cecile (5 mi / 8 km)
  • Lake Tohopekaliga (6.2 mi / 10 km)
  • Lake Bryan (7.5 mi / 12.1 km)
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.

How to get around

Getting around Kissimmee from your vacation rental

It's easy to get around Kissimmee from your vacation home rental using the LYNX public transit system, an inexpensive bus service available throughout the entirety of Central Florida. The SunRail also serves the city and connects to the rest of the greater Orlando area. For shorter trips around town, you can hire taxis, ride-sharing services, or tour buses to see local attractions. Most hotels offer easy and convenient access to shuttle services as well. Or you can take the wheel by hiring a rental car and driving yourself from A to B.

Food & drink 

Fine food to feast on near your Kissimmee vacation rental

Kissimmee's foodie scene combines international flavours with classic all-American diners in its diverse selection of restaurants. Treat your date to a romantic candlelit dinner in European-style bistros, or bring the whole family to a traditional steakhouse or a themed restaurant, where you can enjoy a medieval show with your meal. Asian restaurants can be found aplenty, offering fresh, authentic Japanese or Korean delicacies. Feeling adventurous? Try the spicier flavours served at the lively and colourful Mexican restaurants. Downtown Kissimmee has a cluster of bars and eateries if you feel like sampling a few different menus.

Essential info

Key facts for your stay in Kissimmee

Kissimmee has an estimated 60,000 residents, more than half of whom are Hispanic. Spanish is widely spoken but English is still the official language. It covers an area of 44 sq km roughly 30 km south of Orlando. You can expect hot, humid summers and dry, sunny winters so packing light clothing is recommended. You can grab a drink the local bars if you're over 21, just remember to tip 15–20% of your bill. Staying at Kissimmee vacation rentals isn't particularly expensive and crime rates are low throughout the city. Dial 911 for help in case of an emergency.

How many vacation rentals are available around Kissimmee?

Our 2020 vacation rental listings offer a large selection of 28,757 house rentals around Kissimmee. From 11,863 Houses to 7,738 Villas, find unique vacation rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Kissimmee is on HomeAway.

What is the best area to stay when travelling to Kissimmee?

Whether you're travelling 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:

  • Lake Berkley: 1,163 vacation rentals
  • Cumbrian Lakes: 208 vacation rentals
  • Venetian Bay Villages: 312 vacation rentals
  • Bellavida: 1,196 vacation rentals
  • Eagle Pointe South: 533 vacation rentals

For other neighbourhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when travelling to Kissimmee?

HomeAway offers a large selection of lodging choices near lovely places in Kissimmee. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Reunion Resort Golf Course: 30,743 home rentals
  • Old Town: 30,953 home rentals
  • Kissimmee Lakefront Park: 27,582 home rentals
  • Remington Golf Club: 29 home rentals
  • Mystic Dunes Golf Club: 30,734 home rentals

But there are many other points of interest around Kissimmee listed on HomeAway 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. HomeAway has 11,863 Houses in Kissimmee. Our other popular types of vacation rentals in Kissimmee include:

  • Villas: 7,738 lodging choices
  • Condos/Apartments: 3,786 lodging choices
  • Resorts: 708 lodging choices

But you can also enjoy a great stay in one of our other vacation homes including Townhouses and more.

Can I find a vacation rental with pool in Kissimmee?

Yes, you can select your preferred vacation rental with pool among our 27,088 vacation homes with pool available in Kissimmee.

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