Holiday rentals in Kissimmee
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Travel insights for holiday rentals in Kissimmee
Use these up-to-date, data-driven insights about booking a holiday rental in Kissimmee including ideal times to book, pricing trends, and more.
What is the cheapest month to book a vacation rental in Kissimmee?
The cheapest month to book a vacation rental in Kissimmee is September ($263). Conversely, the most expensive month to stay in Kissimmee is February ($564).
What is the cheapest day to stay in a vacation rental in Kissimmee?
The cheapest day to stay in Kissimmee is Wednesday ($327). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $427.
How far ahead should you book a vacation rental in Kissimmee?
Save money by booking a vacation rental at least 32 days before your trip to Kissimmee. The lowest price found when booking 32 days ahead was $130 per night.
Cheapest holiday rentals in Kissimmee, Florida
Discover affordable stays in Kissimmee that provide a quality experience without breaking the bank. Hotels in Kissimmee can be found for as low as $234 per night. There is currently one property in Kissimmee that can be booked for this price. High Point World Resort is one of the hotels that can be booked for the lowest price in Kissimmee. Price data was last updated on 9 June 2025
Currently, these are the lowest-priced holiday rentals in Kissimmee we've come across for the dates selected. Prices can differ depending on the dates selected, so use the search form to browse more options if you have flexibility.
Show all 20,021 holiday rentals
$234
Avg. per night
Other accommodations in Kissimmee
Find the perfect holiday rental for your stay in Kissimmee. There are 20,021 hotels in Kissimmee and price data was last updated on 9 June 2025. The average price for a hotel in Kissimmee is $246/night.
Show all 20,021 stays
3045 Polynesian Isle Boulevard, Kissimmee, FL, United States
8.6 km from city centre
Free Wi-Fi
Parking
$206
Avg. per night
4944 West Irlo Bronson Memorial Highway, Kissimmee, FL, United States
7.0 km from city centre
Free Wi-Fi
Parking
$46
Avg. per night
7700 Westgate Boulevard, Kissimmee, FL, United States
17.7 km from city centre
Free Wi-Fi
Parking
$143
Avg. per night
5000 Avenue Of The Stars, Kissimmee, FL, United States
7.2 km from city centre
Free Wi-Fi
$206
Avg. per night
7593 Gathering Drive, Kissimmee, FL, United States
17.2 km from city centre
Free Wi-Fi
$299
Avg. per night
5005 Kyng's Heath Road, Kissimmee, FL, United States
7.5 km from city centre
Free Wi-Fi
$267
Avg. per night