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Holiday hires 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 January ($100). Conversely, the most expensive month to stay in Kissimmee is December ($445).

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

The cheapest day to stay in Kissimmee is Tuesday ($154). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $224.

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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 $138 per night. There is currently one property in Kissimmee that can be booked for this price. Vacation Village at Parkway is one of the hotels that can be booked for the lowest price in Kissimmee. Price data was last updated on 8 March 2026
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.
Vacation Village at Parkway
Vacation Village at Parkway

Vacation Village at Parkway

2975 Arabian Nights Boulevard, Kissimmee, FL, United States
11.7 km from city centre
Free Wi-Fi
Parking
$138
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
$263
Avg. per night
View Deal

Other accommodations in Kissimmee

Find the perfect holiday rental for your stay in Kissimmee. There are 17,077 hotels in Kissimmee and price data was last updated on 8 March 2026. The average price for a hotel in Kissimmee is $194/night.
Palazzo Lakeside Hotel
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

4944 West Irlo Bronson Memorial Highway, Kissimmee, FL, United States
7.0 km from city centre
Free Wi-Fi
Parking
$92
Avg. per night
View Deal
Quality Inn & Suites Kissimmee by The Lake
Quality Inn & Suites Kissimmee by The Lake

Quality Inn & Suites Kissimmee by The Lake

7785 West US 192, Kissimmee, FL, United States
18.2 km from city centre
Free Wi-Fi
Parking
$93
Avg. per night
View Deal
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
$166
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
$201
Avg. per night
View Deal
Rodeway Inn Kissimmee Maingate West
Rodeway Inn Kissimmee Maingate West

Rodeway Inn Kissimmee Maingate West

7455 W Irlo Bronson Highway, Kissimmee, FL, United States
16.8 km from city centre
Free Wi-Fi
Air conditioning
$71
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 8 March 2026.
Use the map to find holiday rentals in Kissimmee that are close to the points of interest you'll be frequenting. Users can click on a holiday rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

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 8 March 2026.

  • How much does a holiday rental in Kissimmee cost?

    $194 per night is how much a holiday rental in Kissimmee costs, on average. $52 per night was the cheapest price recently found by our users, though anything for $175 per night or less is a good deal. Keep in mind that Kissimmee holiday rental prices fluctuate throughout the year: the most expensive month to book is February, and the cheapest time to book is February.

  • Are there any Resort holiday rentals in Kissimmee?

    If you’re looking to book a Resort holiday rental in Kissimmee, then you have 346 to choose from. We recommend looking at Maingate Lakeside Resort as it’s currently the most popular Resort rental among our users.

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