Insights
Cheapest hotels
Where to stay

Vacation rentals in Kissimmee

Search and compare Kissimmee, FL vacation rentals from hundreds of travel sites on HotelsCombined and save.

...and more

Learn why travellers love HotelsCombined

Compare hotel ratings collected from thousands of user reviews.

One search gives you accurate pricing on affordable hotels.

Customize your results by hotel chain, amenities, price, and more.

Search for hotels as many times as you want – for free.

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$ 86). Conversely, the most expensive month to stay in Kissimmee is December (C$ 231).

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

The cheapest day to stay in Kissimmee is Friday (C$ 107). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is C$ 240.

Find deals

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$ 94 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 June 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$ 94
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$ 298
Avg. per night
View Deal

Other accommodations in Kissimmee

Find the perfect vacation rental for your stay in Kissimmee. There are 17,188 hotels in Kissimmee and price data was last updated on 8 June 2026. The average price for a hotel in Kissimmee is C$ 179/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$ 61
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$ 74
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
C$ 78
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
C$ 151
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$ 192
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$ 425
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 June 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 June 2026.

  • How much does a vacation rental in Kissimmee cost?

    Kissimmee vacation rentals are C$ 157/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$ 47/night - which is currently the cheapest price. Keep in mind that anything C$ 153/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 631 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, Gaylord Palms Resort & Convention Center is currently the most popular Resort rental in the city.

See more FAQs

Find better results for your stay in Kissimmee