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Day Drinking (Margaritaville Resort, Orlando)
3 3 8 Kissimmee
From $401.00/night

Kissimmee Vacation Rental Guide

Kissimmee, located in central Florida in Osceola County, is a family-friendly vacation hub popular for its proximity to the Walt Disney World Resort complex. Kissimmee also boasts some off-the-beaten-path opportunities. It sits on the northwest shore of Lake Tohopekaliga, Lake Toho for short, and has a fishing pier, walking paths, and playgrounds in its beautiful Kissimmee Waterfront Park.

Many vacationers visiting Orlando’s attractions prefer staying in Kissimmee vacation rental properties because of easy access to the theme parks without the inconvenience of Orlando’s heavy rush hour traffic. Generally speaking, staying in Kissimmee is less expensive than staying in Orlando, with nightly rental rates starting at about $79.  

From Kissimmee, you can get to Cocoa Beach on Florida’s east coast in about 70 minutes. There, you’ll enjoy relaxing on the soft sand, refreshing dips in the cool ocean waters, and visiting a 60-year-old pier. The Kennedy Space Center, one of central Florida’s most popular destinations, is only 50 miles east of Kissimmee and annually hosts over 1.5 million visitors from all over the world.   

Things to Do

Looking to rent a vacation home in Kissimmee? There are endless opportunities for fun, relaxation, and exploration in and around Kissimmee. Kissimmee is right near Disney. Walt Disney World has four theme parks that attract a combined 58 million visitors each year. You can visit each park individually or buy a pass that allows you to experience all four  –  Magic Kingdom ParkAnimal Kingdom Theme ParkHollywood Studios, and Epcot Theme Park.

Other theme parks, water parks, and attractions:  Universal StudiosIslands of Adventures and Volcano BayLEGOLAND Florida, the largest LEGOLAND theme park in the country, is a must-visit for anyone obsessed with Lego. SeaWorld and its sister parks Aquatica and Discovery Cove offer up-close and personal animal shows and experiences.

If you’re traveling with kids and want non-theme park family-friendly activities, here are some options for you.

  1. Shingle Creek. Shingle Creek Regional Park is located at the Headwaters of the Florida Everglades. If you’re an outdoor enthusiast, this 1,000-acre urban oasis will take your breath away. Entry to Shingle Creek Regional Park is free, but you can rent kayaks, canoes, or paddleboards for guided tours or your own leisurely exploration at the Paddling Center.
  2. Old Town. If you’re a history buff, stroll back in time on Old Town’s brick streets. Ride the classic carousel and Ferris wheel, dine, shop, browse through the farmers market, or enjoy some of the many special events scheduled throughout the year.
  3. Medieval Times.   Medieval Times is a family-friendly dinner attraction in which guests enjoy a four-course banquet while rooting for their chosen knight, who competes in hand-to-hand combat, jousting, swordsmanship, horsemanship, and falconry as part of a thrilling and moving story set in medieval Spain. 
  4. Chocolate Kingdom, the Factory Adventure Tour. Chocoholics of all ages will love this interactive journey through the magic of chocolate making. You’ll explore a Cacao Tree Greenhouse, a Chocolate Museum, a magical Mystical River of Chocolate, and a bean-to-candy bar factory. You’ll even have a chance to customize your own chocolate bar.
  5. Water parks and go-karts galore.  There are several water parks of all sizes and designs throughout the area, amusement parks, go-karts, laser tag, skating, bowling, and petting zoos to round out the assortment of experiences your kids are sure to enjoy.

Kissimmee isn’t only for kids, though. Couples traveling without kids will find plenty to see and do. Here are some fun ideas for your adult-only enjoyment.

  1. Titanic:  The Artifact Exhibition. This museum has over 300 artifacts on display, full-scale recreations, and costumed actors to help maximize your experience. You can take a guided tour, attend a First-Class Dinner Gala, and take a photo on the ship’s grand staircase. 
  2. Hot Air Balloon Rides. There are a few companies in the area that offer hot air balloon rides. Aerostat Adventures is one. You can schedule private rides for just the two of you, choose to launch at sunrise, and be part of the crew by participating in the balloon’s inflation. Your flight will last 1-1.5 hours and will be followed by a champagne toast to celebrate the beautiful memories you made.
  3. Lakeridge Winery and Vineyards. Just under an hour away from Kissimmee is Florida’s largest premium winery. At Lakeridge Winery and Vineyards, you can enjoy complimentary wine tasting and tours seven days a week. Weekends at the winery include food from some of the area’s best food trucks, and the many annual events and festivals feature live music, arts and crafts, food, beer, and, of course, award-winning Lakeridge wines.   
  4. Orlando Tree Trek Adventure Park in Kissimmee. Take your adventures to new heights by visiting the area’s most thrilling treetop obstacle adventure park. With a giant 425-foot zipline, 97 aerial challenges, wobbly suspended bridges, swinging logs, and Tarzan ropes, you’ll delight your inner thrill-seeker with a visit to this park featuring outdoor fun for all skill levels.
  5. Playgrounds for big kids. There are many places for adults to play in and around Kissimmee.  There are escape rooms, go-karts, arcades, bowling lanes, and laser tag. You can tour a haunted mansion complete with a burial simulation and enjoy numerous dinner theater experiences. 

If you’re a golfer, you’ll find plenty of golf courses to challenge you on your getaway in Kissimmee, and the dining options are virtually unlimited. These are only a few of the fun things to see and do in and around Kissimmee.  

Getting Here

No matter how you’re traveling or where you’re coming from, reaching Kissimmee is simple and straightforward because of its convenient location in central Florida.  

You have three good options if you plan to travel by air. The nearest airport is the Kissimmee Gateway Airport (ISM), about 2 miles from Kissimmee’s city center and the closest airport to the heart of the greater Orlando metro area’s primary tourism and business hubs. It’s a small airport and can get you where you need to be as stress-free as possible.

If you can’t find flight accommodations that work for you at Kissimmee Gateway, you can fly into Orlando International Airport (MCO), a 17-mile or 30-minute drive from Kissimmee, or the Orlando Sanford International Airport (SFB), about  46 miles or 55 minutes away. Between the two, nearly all major airlines fly into the Orlando/Kissimmee area, making it easily accessible by air.

If you’re traveling by rail, you’re in luck, because the Kissimmee train station is the Amtrak station closest to Walt Disney World. It’s located in the Historic Downtown Kissimmee’s Intermodal station, as is the Greyhound bus terminal.


Kissimmee is known for long, hot summers and short, mild winters. January is the coldest month of the year. Even then, temperatures average in the 70s, and skies are sunny and clear. Since it’s not peak travel time for this area, vacation rentals will be priced low.

If you plan to do warm-weather activities during your visit, the best time for your trip to Kissimmee would be from early March to mid-May or from mid-October to early December. Temperatures are mild in spring and fall, with highs in the 60s-80s, and it’s still off-peak, meaning rental prices are still affordable. Fall is hurricane season, so keep an eye on local forecasts if you travel during autumn.

The summer months are hot – sometimes oppressively so. It’s the busiest time of the year for travel into the central Florida area, so look for vacation rentals with air-conditioning and swimming pools. You might pay higher nightly rates at the peak of the summer season but will still find good values in Kissimmee.

Popular Areas

If you’re not certain where to stay during your Kissimmee vacation, here are some popular areas with lots of high-quality vacation rental properties you might consider.

  1. Sunset Lakes, west of Kissimmee city center, near the Walt Disney parks.
  2. Lake Berkley, near Kissimmee Gateway Airport, near the Walt Disney parks.
  3. Historic Downtown Kissimmee, near the city center and historic downtown area, near Lake Tohopekaliga.

Wherever you stay, however you get there, whatever the time of year, you’ll be sure to find something for everyone and a vacation rental property that perfectly meets your needs on a trip to Kissimmee and the surrounding area.  

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