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Vacation 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 May ($96). Conversely, the most expensive month to stay in Kissimmee is March ($231).

What is the cheapest day to stay in a vacation rental in Kissimmee?

The cheapest day to stay in Kissimmee is Sunday ($98). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $143.

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 $78 per night.

Other accommodations in Kissimmee

Find the perfect holiday rental for your stay in Kissimmee. There are 22,081 hotels in Kissimmee and price data was last updated on 11 July 2025. The average price for a hotel in Kissimmee is $143/night.
7593 Gathering Drive, Kissimmee, FL, United States
17.2 km from city centre
Free Wi-Fi
$188
Avg. per night
5000 Avenue Of The Stars, Kissimmee, FL, United States
7.2 km from city centre
Free Wi-Fi
$125
Avg. per night
5005 Kyng's Heath Road, Kissimmee, FL, United States
7.5 km from city centre
Free Wi-Fi
$148
Avg. per night
4944 West Irlo Bronson Memorial Highway, Kissimmee, FL, United States
7.0 km from city centre
Free Wi-Fi
Parking
$63
Avg. per night
7430 Brooklyn Drive, Kissimmee, FL, United States
17.5 km from city centre
Free Wi-Fi
Parking
$246
Avg. per night
7700 Westgate Boulevard, Kissimmee, FL, United States
17.7 km from city centre
Free Wi-Fi
Parking
$109
Avg. per night

Where to stay in Kissimmee

Explore different neighbourhoods and areas within Kissimmee to find the perfect location for your stay. Map data was last updated on 11 July 2025.
Utilize the map to find properties close to the Kissimmee area(s) or attractions you plan on visiting. You can find more information on a particular vacation rental within the map by clicking on its name.

Facts about staying in Kissimmee

Find useful tips and insights about staying in Kissimmee to help you make the most of your experience. FAQs were last updated on 11 July 2025.
  • How much does a holiday rental in Kissimmee cost?

    The average cost for a holiday rental in Kissimmee is $143/night. A good holiday rental deal in Kissimmee would be for $119/night or less. The cheapest rental deal found recently by our users was $33/night. If you’re flexible with your travel dates, then try to avoid booking July, the most expensive month of the year. Booking May is the cheapest month to book a holiday rental in Kissimmee.

  • Are there any Resort holiday rentals in Kissimmee?

    Yes, there are 346 Resort holiday rentals in Kissimmee. According to our data, Magic Moment Resort And Kids Club is currently the most popular Resort rental in the city.

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