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Vacation rentals in Kissimmee

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Travel insights for vacation rentals in Kissimmee

Use these up-to-date, data-driven insights about booking a vacation 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 (C$ 95). Conversely, the most expensive month to stay in Kissimmee is December (C$ 424).

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

The cheapest day to stay in Kissimmee is Tuesday (C$ 147). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is C$ 213.

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Cheapest vacation 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 C$ 131 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
These Kissimmee properties charge the lowest price per night of those we've come across. 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
C$ 131
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
C$ 253
Avg. per night
View Deal

Other accommodations in Kissimmee

Find the perfect vacation rental for your stay in Kissimmee. There are 17,075 hotels in Kissimmee and price data was last updated on 8 March 2026. The average price for a hotel in Kissimmee is C$ 185/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
C$ 159
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
C$ 191
Avg. per night
View Deal
Gaylord Palms Resort & Convention Center
Gaylord Palms Resort & Convention Center

Gaylord Palms Resort & Convention Center

6000 West Osceola Parkway, Kissimmee, FL, United States
11.5 km from city centre
Free Wi-Fi
C$ 447
Avg. per night
View Deal
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
C$ 89
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.
Scroll through the map to find vacation rentals close to the Kissimmee neighborhood(s) you plan on visiting. More information on a given vacation rental can be accessed by clicking the vacation 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 8 March 2026.

  • How much does a vacation rental in Kissimmee cost?

    Kissimmee vacation rentals are C$ 185/night on average. However, you may find that prices fluctuate depending on the time of year. For example, February is the most expensive month to book a vacation rental in Kissimmee, and February is often the cheapest month to book. Recently, our users found rentals for C$ 49/night - which is currently the cheapest price. Keep in mind that anything C$ 167/night or less is still considered a good deal.

  • Are there any Resort vacation rentals in Kissimmee?

    Yes, there are 346 Resort vacation rentals in Kissimmee. According to our data, Maingate Lakeside Resort is currently the most popular Resort rental in the city.

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