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Vacation rentals 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 June (S$ 165). Conversely, the most expensive month to stay in Kissimmee is May (S$ 489).

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

The cheapest day to stay in Kissimmee is Sunday (S$ 164). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is S$ 368.

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

Save money by booking a vacation rental at least 87 days before your trip to Kissimmee. The lowest price found when booking 87 days ahead was S$ 82 per night.
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Other accommodations in Kissimmee

Find the perfect holiday rental for your stay in Kissimmee. There are 22,021 hotels in Kissimmee and price data was last updated on 16 September 2025. The average price for a hotel in Kissimmee is S$ 191/night.
Star Island Resort and Club - Near Disney
Star Island Resort and Club - Near Disney

Star Island Resort and Club - Near Disney

5000 Avenue Of The Stars, Kissimmee, FL, United States
7.2 km from city centre
Free Wi-Fi
S$ 137
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
S$ 180
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
S$ 389
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 16 September 2025.
Scroll through the map to find vacation rentals close to the Kissimmee neighborhood(s) you plan on visiting. Users can click on a vacation 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 16 September 2025.

  • How much does a holiday rental in Kissimmee cost?

    On average, it costs S$ 191 per night for a Kissimmee holiday rental, but S$ 168 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Kissimmee was for S$ 51 per night. If you can, try to avoid booking your rental September (as this is the most expensive month). Booking June (the cheapest month) may end up saving you money.

  • Are there any Resort holiday rentals in Kissimmee?

    There are 346 holiday rentals in Kissimmee that fall under the Resort category, the most popular is Maingate Lakeside Resort.

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