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.


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 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.

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, FL?

Our 2020 property listings offer a large selection of 25,375 vacation rentals around Kissimmee. From 10,436 house rentals to 6,559 villa rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a resort property in Kissimmee?

Treat your squad to an extraordinary vacation that perfectly combines relaxation, recreation and pleasure. A resort escape is the perfect break from day to day life. Vrbo has 10,912 getaway rentals located within resorts available. Of course, that might not be your style. Luckily, Vrbo has plenty of other choices, including:

  • 2,716 city-center vacation rentals.
  • 1,209 lakefront vacation rentals.
  • 1,162 lakeside vacation rentals.

Can I rent a house in Kissimmee?

Wave goodbye to standard, cookie-cutter hotel rooms. Our house vacation rentals offer a personal touch — as well as all the space you could need! There are 15,740 options currently on Vrbo. Prices start from $16 per night. Or maybe you'd rather choose one of the area's other popular property options, such as:

  • Villa: 9,996 vacation homes. Prices start from $44 per night.
  • Townhome: 5,447 vacation homes. Prices start from $60 per night.
  • Condo: 4,042 vacation homes. Prices start from $34 per night.

Can I stay in Kissimmee in a large group?

The recipe for a perfect vacation is relaxing with friends and family in an exciting new place. If you'll be traveling with a large group, Vrbo has options. Presently, house vacation homes are the hottest thing for large groups of visitors here, and you'll find 3,017 featured on our database. Rental accommodations in the area that are suitable for large groups include:

  • If yours is a group of 8, we've got 8,990 vacation homes suitable for that size. Stay a night for as little as $60.
  • If you've got 10 in your party, you'll be happy to find out that there are 6,579 vacation homes that are ideal. The starting price is $69 a night.
  • On a trip away with a group of 12? We offer 4,869 vacation homes that match your requirements. Prices begin at just $96 a night.

You and your posse will be more than satisfied when you book your Kissimmee escape through us!

Where are the cheapest rentals in Kissimmee?

Say au revoir to samey chain-hotel rooms! Delight in the charm of living like a local in a budget-friendly rental instead. Feast your eyes on the wonderful options that can be snapped up now on Vrbo. Downtown is a terrific area to consider if you want to keep an eye on your budget. Vrbo has 47 rentals, and the average price is a very affordable $141 per night. There are another 2,167 Vrbo rentals awaiting you in or around Regal Palms. The average price in this area is $150 per night.

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