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We found 22,597 vacation rentals — enter your dates for availability
Discover a selection of more than 10,000 vacation rentals in Kissimmee that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including private pools and swimming pools. Prices start at $136 per night, and houses and resorts are popular options for a stay in Kissimmee. Either way, you'll find a rental for everyone's needs.
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Find the best place to stay — Kissimmee
Top rated rentals — Kissimmee
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Destination guide
Experience Kissimmee with your pet in a vacation rental
If you're looking for pet-friendly rentals while you vacation in Florida, Kissimmee is a great option. Located in central Florida, Kissimmee is close enough to all the attractions but far enough away from Orlando that you can find great pet-friendly rentals at cheaper prices. There are plenty of things to do in Kissimmee, whether you're looking for daytime activities or nighttime entertainment. Within 30 minutes, you can be at Walt Disney World Resort. With fun for kids and adults alike, Kissimmee really is an optimal place to stay.
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.
How many vacation rentals are available around Kissimmee?
Our 2021 property listings offer a large selection of 22,597 vacation rentals around Kissimmee. From 17,960 house rentals to 980 resort rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.