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Kissimmee Vacation Rentals

Our Favorite Vacation Rentals in Kissimmee

Kissimmee Vacation Rentals with a Pool

Kissimmee Vacation Rentals with Wi-Fi

Kissimmee Pet-Friendly Vacation Rentals

Kissimmee Travel Guide

Located just south of Orlando, Kissimmee is a small city with a big reputation for theme parks and world-class vacation rentals. Warm weather, endless activities for the kids, good food and a plenty of golf courses make the city a perfect family getaway.

Things to Do in Kissimmee

Kissimmee is known for its wealth of Airbnbs and other short-term vacation rental properties. Families looking for hotels stay up north in the Orlando, but families looking to escape the crowds but still have the parks at their fingertips tend to opt for larger homes and condos in Kissimmee. The rentals are generally spacious homes with private pools and easy access to nearby golf courses. Many sit on Lake Tohopekaliga and set guests up with gorgeous sunset views.

Best Time to Visit Kissimmee

Most visitors book their homes and condos in the winter to escape the northern cold and take in the Florida sun. The spring and fall are also nice and visitors benefit from offseason price dips. The summer is hot and humid and better avoided.

A Local's Guide to Kissimmee Vacation Rentals

The often overlooked jewel of central Florida, Kissimmee offers traveler’s all of the perks and Disney Parks access of Orlando with the added benefit of outdoor adventures along Lake Toho (Lake Tohopekaliga).

The lovely town of Kissimmee is located in Osceola County, Florida just a mere 11 miles from Walt Disney World and 19 miles from Universal Studios, making it the perfect rental destination for families looking for a mix of park access and relaxation.

Family Activities

The community in Kissimmee is family-oriented and there are plenty of off-the-beaten-path activities to do to keep the whole family entertained.

An ideal day in Kissimmee, Florida includes a trip to Disney World with the family, a tour of the Kennedy Space Center, and an unforgettable fan boat experience on Lake Tohopekaliga. Other popular experiences in Kissimmee include scenic treetop zip line tours, hot air balloon adventures, and of course boutique shopping in Kissimmee’s charming downtown area.

When to Book

The classic Florida scene of sunshine and palm trees makes Kissimmee the perfect winter getaway during the bitter cold months of the year. During the summer months, Kissimmee is the ideal destination to avoid the crowds of Orlando, while having access to Florida’s best theme parks.

Price and Availability in Kissimmee

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The most expensive month to stay in a vacation rental in Kissimmee is in July, while the cheapest month is in September. The most popular time to book a vacation rental in Kissimmee is in the high season in March. Kissimmee has its low season in September, when less people are visiting and the vacation home occupancy rate drops.
The cheapest day to stay at a vacation rental in Kissimmee tends to be Monday, while the most expensive day tends to be Saturday. Vacation homes in Kissimmee tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.

The Weather in Kissimmee

95º 72º
94º 71º
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92º 52º
89º 39º
87º 40º
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92º 61º
95º 70º
Rainy days
This climate histogram shows you the weather patterns in Kissimmee. The warmest months in Kissimmee are June and July, when temperatures reach 95 ˚F. The coolest month is March, when temperatures drop to 37 ˚F. The wettest month in Kissimmee is May with 7.7 inches of rain, while the driest month is February with 0.16 inches of rain.

What Expert Travelers Think

Vacation Rentals in Kissimmee

Browse accommodations from all the best providers including Airbnb, RedAwning, TUIVillas and others at We have 113,110 vacation rentals, hotels and other accommodation types in Kissimmee ranging from cheap options to luxury places to stay. The average price of a rental is generally $645 per night.

If you would like to stay connected during your trip, then you can choose from over 33,121 accommodations in Kissimmee that have WiFi. 460 of our accommodations include a breakfast in the price. You can maintain your workout routine by staying at one of 16,770 accommodations that provide gym facilities. Driving to Kissimmee? Then choose one of the 27,585 places to stay that comes with a parking spot included. We track 23,058 places to stay that have a pool or jacuzzi.

AllTheRooms has 2,202 pet-friendly places to stay in Kissimmee, so if you're traveling with your pet you won't have any problems.

We combine a wide variety of Kissimmee accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 6 providers, including 19,548 places to stay from Airbnb, 2,768 accommodations from RedAwning and 857 places to stay from TUIVillas.

23,569 of the rentals in Kissimmee have been rated by previous guests. They rated 18% as great. 43,238 places to stay in are instantly bookable.

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