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Vacation rentals in Kissimmee

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Travel insights for vacation rentals in Kissimmee

Use our HotelsCombined data-powered tips to help you find your next vacation rental in Kissimmee.

What is the cheapest month to book a vacation rental in Kissimmee?

The cheapest month to book a vacation rental in Kissimmee is August (C$ 87). Conversely, the most expensive month to stay in Kissimmee is December (C$ 271).

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

The cheapest day to stay in Kissimmee is Friday (C$ 108). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is C$ 242.

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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$ 119 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 23 July 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
C$ 119
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$ 274
Avg. per night
View Deal

Other accommodations in Kissimmee

Find the perfect vacation rental for your stay in Kissimmee. There are 16,883 hotels in Kissimmee and price data was last updated on 23 July 2026. The average price for a hotel in Kissimmee is C$ 169/night.
Rodeway Inn Kissimmee Maingate West
Rodeway Inn Kissimmee Maingate West

Rodeway Inn Kissimmee Maingate West

7455 West Irlo Bronson Highway, Kissimmee, FL, United States
16.8 km from city centre
Free Wi-Fi
Air Conditioning
C$ 51
Avg. per night
View Deal
Palazzo Lakeside Hotel Kissimmee
Palazzo Lakeside Hotel Kissimmee

Palazzo Lakeside Hotel Kissimmee

4944 West Irlo Bronson Memorial Highway, Kissimmee, FL, United States
7.0 km from city centre
Free Wi-Fi
Parking
C$ 72
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$ 421
Avg. per night
View Deal
Comfort Suites Maingate East
Comfort Suites Maingate East

Comfort Suites Maingate East

2775 Florida Plaza Boulevard, Kissimmee, FL, United States
9.9 km from city centre
Free Wi-Fi
C$ 119
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 23 July 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 23 July 2026.

  • How much does a vacation rental in Kissimmee cost?

    Kissimmee vacation rentals are C$ 149/night on average. However, you may find that prices fluctuate depending on the time of year. For example, December is the most expensive month to book a vacation rental in Kissimmee, and January is often the cheapest month to book. Recently, our users found rentals for C$ 73/night - which is currently the cheapest price. Keep in mind that anything C$ 145/night or less is still considered a good deal.

  • What is the best Kissimmee vacation rental?

    Westgate Vacation Villas Resort has a 7.2 rating from 622 users, making it the best Kissimmee vacation rental based on our data.

  • What’s the closest vacation rental to Orlando Airport?

    It’s only 30.4 km from Orlando Airport to Westgate Vacation Villas Resort (the nearest Kissimmee vacation rental to the airport).

  • Are there any Resort vacation rentals in Kissimmee?

    Yes, there are 346 Resort vacation 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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