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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 September (C$ 124). Conversely, the most expensive month to stay in Kissimmee is May (C$ 418).

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

The cheapest day to stay in Kissimmee is Wednesday (C$ 146). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is C$ 586.

How far ahead should you book a vacation rental in Kissimmee?

Save money by booking a vacation rental at least 25 days before your trip to Kissimmee. The lowest price found when booking 25 days ahead was C$ 84 per night.
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Other accommodations in Kissimmee

Find the perfect vacation rental for your stay in Kissimmee. There are 17,173 hotels in Kissimmee and price data was last updated on 23 October 2025. The average price for a hotel in Kissimmee is C$ 203/night.
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$ 247
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
C$ 189
Avg. per night
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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$ 482
Avg. per night
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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$ 82
Avg. per night
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Spectrum Resort Orlando by Rentyl
Spectrum Resort Orlando by Rentyl

Spectrum Resort Orlando by Rentyl

7750 Sandy Ridge Drive, Kissimmee, FL, United States
17.3 km from city centre
Air Conditioning
C$ 337
Avg. per night
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Hilton Vacation Club Polynesian Isles Kissimmee
Hilton Vacation Club Polynesian Isles Kissimmee

Hilton Vacation Club Polynesian Isles Kissimmee

3045 Polynesian Isle Boulevard, Kissimmee, FL, United States
8.6 km from city centre
Free Wi-Fi
Parking
C$ 162
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 October 2025.
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 October 2025.

  • How much does a vacation rental in Kissimmee cost?

    Kissimmee vacation rentals are C$ 203/night on average. However, you may find that prices fluctuate depending on the time of year. For example, October is the most expensive month to book a vacation rental in Kissimmee, and November 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$ 176/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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