Discover a selection of more than 10,000 vacation rentals in Kissimmee, FL 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 $90 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.
Top rated rentals — Kissimmee
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.


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 2021 property listings offer a large selection of 23,837 vacation rentals around Kissimmee. From 18,249 house rentals to 1,284 resort rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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:

  • Windsor Hills: 2,350 vacation rentals
  • Lake Berkley: 814 vacation rentals
  • Eagle Pointe South: 360 vacation rentals
  • Bellavida: 831 vacation rentals
  • Cumbrian Lakes: 134 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Kissimmee?

Vrbo offers a large selection of vacation rentals near lovely places in Kissimmee. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Reunion Resort Golf Course: 26,056 vacation rentals
  • Old Town: 26,298 vacation rentals
  • Kissimmee Lakefront Park: 22,323 vacation rentals
  • Remington Golf Club: 22 vacation rentals
  • Mystic Dunes Golf Club: 26,098 vacation rentals

But there are many other points of interest around Kissimmee listed on Vrbo 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. Vrbo has 18,249 Houses in Kissimmee. Our other popular types of vacation rentals in Kissimmee include:

  • Resorts: 1,284 rentals available
  • Villas: 4,906 rentals available
  • Cabins: 48 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Townhouses and more.

Can I find a vacation rental with pool in Kissimmee?

Yes, you can select your preferred vacation rental with pool among our 22,584 vacation rentals with pool available in Kissimmee. Please use our search bar to access the selection of vacation rentals available.

Explore destinations around Kissimmee

Windsor Hills
2,350 vacation rentals
Lake Berkley
814 vacation rentals
Eagle Pointe South
360 vacation rentals
831 vacation rentals
Cumbrian Lakes
134 vacation rentals
2,180 vacation rentals
Chatham Park
316 vacation rentals
Sunset Lakes
4,266 vacation rentals
Indian Point
1,798 vacation rentals
Veranda Palms
645 vacation rentals
Historic Downtown Kissimmee
263 vacation rentals
Crescent Lakes
98 vacation rentals
Venetian Bay Villages
258 vacation rentals
Indian Wells
636 vacation rentals
Crystal Cove
698 vacation rentals
349 vacation rentals
Trafalgar Village
30 vacation rentals
Crestwynd Bay
1,766 vacation rentals
226 vacation rentals
Indian Ridge
790 vacation rentals