Kissimmee, FL vacation rentals: Houses & more

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Destination guide

Explore Kissimmee from vacation home rentals

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.

History

Historic sites near Kissimmee vacation homes

Kissimmee has numerous historic sites and museums to explore during your trip. Vacation rentals are available near fascinating places like the Museum of Military History, a museum with military relics, photographs, and personal stories, and Osceola County Welcome Center and History Museum, a local history museum with dioramas and interactive exhibits of the county’s history. You can also visit the Monument of the States, a mid-century monument with stones sourced from the 50 states to celebrate American unity.

Things to do

Places to visit near Kissimmee vacation rentals

Don't list the attractions in Kissimmee out loud to your kids. The excitement might be too much for them. Luckily, the amusements on offer are fun for grown-ups, too. Green Meadows Farm is a peaceful countryside getaway where you can pet the animals, milk a cow, and have a picnic on the grass. Gatorland is a theme park with a playful, vintage feel. There are live animal shows and plenty of alligators in its breeding marsh, and you can buy hot dogs to feed them. Fun Spot America features old-time carnival rides and go-kart tracks.

Activities

Activities near Kissimmee vacation homes

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

Best time to travel to Kissimmee vacation homes

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.

Good for couples

Couple's retreat in Kissimmee vacation homes

Couples will find plenty of romantic experiences and locations in Kissimmee. Vacation homes are available near places like Lake Tohopekaliga, a huge fishing lake with wildlife viewing, airboat rides, and swimming, and Kissimmee Lakefront Park, a waterside park with walking paths and fishing areas. You’ll also enjoy Main Gate Flea Market, an indoor flea market with booths selling clothing, accessories, and other goods.

Can I find a vacation rental around Kissimmee?

Yes, our 2019 property listings offer a large selection of 39,612 vacation rentals near Kissimmee. From 14,533 Houses to 12,657 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 HomeAway.

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:

Cumbrian Lakes: 254 vacation rentals
Lake Berkley: 1,484 vacation rentals
Venetian Bay Villages: 396 vacation rentals
Bellavida: 1,523 vacation rentals
Eagle Pointe South: 647 vacation rentals

For other neighborhoods, 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 traveling to Kissimmee?

HomeAway offers a large selection of vacation rentals 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: 42,699 vacation rentals
Kissimmee Lakefront Park: 38,522 vacation rentals
Remington Golf Club: 39 vacation rentals
Old Town: 41,896 vacation rentals
Mystic Dunes Golf Club: 41,547 vacation 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 14,533 Houses in Kissimmee. Our other popular types of vacation rentals in Kissimmee include:

Villas: 12,657 rentals available
Condos/Apartments: 4,351 rentals available
Townhouses: 6,546 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 37,242 vacation rentals with pool available in Kissimmee. Please use our search bar to access the selection of vacation rentals available.