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Kissimmee Vacation Rentals

Our Favorite Vacation Rentals in Kissimmee

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Kissimmee Vacation Rentals with a Pool

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Kissimmee Vacation Rentals with Wi-Fi

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Kissimmee Pet-Friendly Vacation Rentals

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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

92º 61º
7.7
95º 70º
3.18
95º 72º
0.74
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3.32
92º 52º
1.71
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2.03
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1.92
88º 47º
0.16
87º 37º
0.2
90º 51º
0.91
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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

At AllTheRooms.com we have vacation rentals from all of the best providers - Airbnb, Homeaway, RedAwning and many more. AllTheRooms has 109,866 rentals, hotels and other great places to stay during your time in Kissimmee, with everything from cheap hostels and homestays to luxury Airbnbs and hotels. An average accommodation in Kissimmee costs on average $249 a night.

Those needing to get some work finished during their trip to Kissimmee can pick from 32,223 places to stay that provide WiFi. We have 376 accommodations that include a breakfast included. Fitness fanatics can get a workout in during their stay by choosing from 15,415 accommodations that have gyms. If you're planning on arriving in Kissimmee by car, be sure to choose from 26,402 accommodations that provide parking. 20,623 accommodations come with a pool or jacuzzi

If you're traveling with your best friend, then be sure to select one of the 2,224 pet-friendly accommodations available.

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 10 providers, including 16,861 places to stay from Airbnb, 10,501 accommodations from Homeaway and 2,853 places to stay from RedAwning.

20,502 of our accommodations in Kissimmee have been reviewed by previous guests. They rated 17% as excellent or good. You can instantly book any of 43,087 places to stay right now.

Destinations near Kissimmee