Holiday hires in Kissimmee
Search and compare Kissimmee, FL holiday rentals from hundreds of travel sites on HotelsCombined and save.
Kissimmee, United States
2 May — 3 May2
...and more
Learn why travellers love HotelsCombined
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 ($279). Conversely, the most expensive month to stay in Kissimmee is December ($631).
What is the cheapest day to stay in a vacation rental in Kissimmee?
The cheapest day to stay in Kissimmee is Sunday ($275). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $636.
How far ahead should you book a vacation rental in Kissimmee?
Save money by booking a vacation rental at least 19 days before your trip to Kissimmee. The lowest price found when booking 19 days ahead was $138 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 $227 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 25 April 2025
At the moment, these holiday rentals offer the lowest nightly rate out of those we've come across in Kissimmee. Prices can differ depending on the dates selected, so use the search form to browse more options if you have flexibility.
Show all 20,173 holiday rentals
$227
Avg. per night
Other accommodations in Kissimmee
Find the perfect holiday rental for your stay in Kissimmee. There are 20,173 hotels in Kissimmee and price data was last updated on 25 April 2025. The average price for a hotel in Kissimmee is $253/night.
Show all 20,173 stays
3045 Polynesian Isle Boulevard, Kissimmee, FL, United States
8.6 km from city centre
Free Wi-Fi
Parking
$188
Avg. per night
5245 West Irlo Bronson Memorial Highway, Kissimmee, FL, United States
8.1 km from city centre
Free Wi-Fi
$249
Avg. per night
2775 Florida Plaza Boulevard, Kissimmee, FL, United States
9.9 km from city centre
Free Wi-Fi
Parking
$161
Avg. per night
7785 West US 192, Kissimmee, FL, United States
18.2 km from city centre
Free Wi-Fi
Parking
$122
Avg. per night
7769 West Irlo Bronson Memorial Highway, Kissimmee, FL, United States
17.9 km from city centre
Free Wi-Fi
Parking
$67
Avg. per night
7593 Gathering Drive, Kissimmee, FL, United States
17.2 km from city centre
Free Wi-Fi
$278
Avg. per night
2754 Florida Plaza Boulevard, Kissimmee, FL, United States
10.2 km from city centre
Free Wi-Fi
$190
Avg. per night