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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 May ($264). Conversely, the most expensive month to stay in Kissimmee is February ($604).

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

The cheapest day to stay in Kissimmee is Tuesday ($277). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $410.

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 $129 per night.
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Other accommodations in Kissimmee

Find the perfect holiday rental for your stay in Kissimmee. There are 22,007 hotels in Kissimmee and price data was last updated on 25 July 2025. The average price for a hotel in Kissimmee is $228/night.
Star Island Resort And Club
Star Island Resort And Club

Star Island Resort And Club

5000 Avenue Of The Stars, Kissimmee, FL, United States
7.2 km from city centre
Free Wi-Fi
$207
Avg. per night
View Deal
Reunion Resort & Golf Club
Reunion Resort & Golf Club

Reunion Resort & Golf Club

7593 Gathering Drive, Kissimmee, FL, United States
17.2 km from city centre
Free Wi-Fi
Spa
$333
Avg. per night
View Deal
Fantasyworld Resort
Fantasyworld Resort

Fantasyworld Resort

5005 Kyng's Heath Road, Kissimmee, FL, United States
7.5 km from city centre
Free Wi-Fi
$244
Avg. per night
View Deal

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 25 July 2025.
Scroll to and zoom in on the areas in Kissimmee you plan on visiting to find nearby properties. More information on a given holiday rental can be accessed by clicking the holiday rental's name within the map.

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 25 July 2025.

  • How much does a holiday rental in Kissimmee cost?

    $229/night is a typical cost for a holiday rental in Kissimmee throughout the year. Rental prices do vary though, and you’ll find that February is the most expensive month to book, and July is the cheapest month to book. HotelsCombined users recently found Kissimmee holiday rentals for as low as $51/night. In general, any Kissimmee rental for $186 or less is a good deal.

  • Are there any Resort holiday rentals in Kissimmee?

    At the moment, there are 346 properties listed as a Resort holiday rental in Kissimmee. A popular Resort in Kissimmee amongst our users is Gaylord Palms Resort & Convention Center.

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