Kissimmee vacation rentals

We found 31,019 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Kissimmee by choosing from 15016 houses, 1764 apartments, and other vacation rentals. Vacation homes provide the best amenities for you and your friends, family, or even pets, like WiFi and parking. At the end of the day, you'll find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.
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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.

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.

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 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.

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.

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 to and around Kissimmee

The nearest airport is in Orlando Intl. Airport (MCO), located 11.4 mi (18.3 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Kissimmee, FL (ISM-Kissimmee Gateway), which is 1.8 mi (2.9 km) away.

If you're traveling by train, the main station is Kissimmee Station. Consider catching the metro at Tupperware Station or Poinciana Station to see more of the city.

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.

Frequently asked questions

What is the best area to stay in Kissimmee when booking a vacation rental?
Bellavida is among the more in-demand neighborhoods for a vacation home in Kissimmee. Spend your stay here to enjoy all the privacy and comfort that comes with having the entire place to yourself.
What is the most popular type of vacation rental accommodation in Kissimmee?
Villas are the most popular kind of vacation rental in Kissimmee, according to our data. Even if you have something different in mind, Vrbo has properties in a variety of sizes and shapes. Look over our options to find your perfect pad.
How much does it cost to rent a vacation rental in Kissimmee?
The average price for a vacation home in Kissimmee is based on several factors, including season, property type and length of stay. Whether you’re dreaming about a sprawling villa with lots of space or a cozy condo for just you and your sweetheart, just enter your dates of travel to find stays with terrific value.
How much does it cost to rent a beach house in Kissimmee?
When you travel and the size and style of the property will help determine the cost of your beachside escape. Type in your Kissimmee travel dates to see all your options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to pick the amenities and features you want in your rental.
Are there pet-friendly vacation rentals in Kissimmee?
Pack a travel bag for your puppy dog because Kissimmee has 20,419 properties that roll out the welcome mat to pets. Let your happy hound join in with the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check the “Pets allowed” filter box.
Can I rent a house with a pool in Kissimmee?
Grab your swimsuit and pool noodle, because there are 19,323 houses with a private pool in Kissimmee. Unwind at one of these terrific vacation rentals and enjoy a pool day every day. Simply enter your dates into Vrbo, then check the “pool” filter to find the ideal place for a splashing good time!
What are popular rental amenities in Kissimmee?
A water view, a garden and an electric car charging station top the list of most popular rental amenities in Kissimmee. Whether you plan to go alone, with a partner or a group of dear friends, Vrbo will help you find a vacation rental that fits your tastes with all the conveniences you’re looking for.
Are there large group vacation rentals in Kissimmee?
Kissimmee has 9,105 vacation homes that can accommodate 10 or more people. These stays come with enough space to share good times with family and friends.
Are there vacation rentals in Kissimmee that welcome kids?
Gather your whole crew for fun-filled adventures in Kissimmee at one of our 19,863 family-friendly vacation rentals. Lots of these stays come with amenities that are ideally suited to trips with youngsters, including full kitchens, extra bedrooms and pools. Just click on the “Properties good for families” filter and pick your favorite option.
What are the top attractions for families in Kissimmee?
Keeping the kids entertained during your Kissimmee vacation is child’s play with these top family-friendly attractions:

  • Kissimmee Golf Club
  • Osceola Square Mall
  • 192 Flea Market

Are there one-bedroom vacation rentals in Kissimmee?
Yes, Kissimmee has 719 one-bedroom rentals available. Typically located in desirable areas because of their smaller size, a one-bedroom vacation property is perfect if you’re traveling with your partner or a friend. And with plenty of home comforts like laundry facilities and more privacy than a standard hotel, you’ll be able to kick back and relax while sightseeing around this amazing destination.
Can I find two-bedroom vacation rentals in Kissimmee?
Gather your loved ones and enjoy total privacy and comfort in one of the 1,495 two-bedroom vacation homes Kissimmee has to offer.
Are there vacation rentals with WiFi in Kissimmee?
Kissimmee has 6,862 vacation rentals with WiFi, so you can stay connected while you’re traveling. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming movies with the family to updating your social media, these Vrbo homes make it a cinch to get online.
How can I find vacation rentals with air conditioning in Kissimmee?
Pick from 19,898 vacation homes with air conditioning in Kissimmee offering that cooling breeze and extra level of comfort. Just enter your preferred dates of travel and then make use of our filter tool to search for properties with air conditioning.
How old do you have to be to rent a vacation rental in Kissimmee?
We advise checking with the Kissimmee vacation rental you’re considering on Vrbo as the age limit differs. However, normally it’s 16, 18 or 21.
How long can I rent a vacation rental in Kissimmee for?
The length of time you can book a vacation rental in Kissimmee is down to the property. Simply enter your chosen dates to display a list of options offering extended stays. With lots of features like washing machines and kitchens, as well as some offering weekly or monthly discounts, you’re sure to find somewhere just right to call your home away from home in Kissimmee.
Does Vrbo offer discounts for vacation homes in Kissimmee?
Whether you’re interested in one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to find some fabulous bargains and discounts on Vrbo. From mini stays to extended vacations, we’ve got the ideal space for your next Kissimmee escape.

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