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Holiday hires 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 ($233). Conversely, the most expensive month to stay in Kissimmee is May ($693).

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

The cheapest day to stay in Kissimmee is Sunday ($232). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $521.

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

Save money by booking a vacation rental at least 32 days before your trip to Kissimmee. The lowest price found when booking 32 days ahead was $119 per night.
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Other accommodations in Kissimmee

Find the perfect holiday rental for your stay in Kissimmee. There are 22,068 hotels in Kissimmee and price data was last updated on 8 September 2025. The average price for a hotel in Kissimmee is $227/night.
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
$93
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
Spa
$122
Avg. per night
View Deal
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
$178
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
$223
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 September 2025.
Use the map to find holiday rentals in Kissimmee that are close to the points of interest you'll be frequenting. Users can click on a holiday 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 8 September 2025.

  • How much does a holiday rental in Kissimmee cost?

    $227 per night is how much a holiday rental in Kissimmee costs, on average. $61 per night was the cheapest price recently found by our users, though anything for $200 per night or less is a good deal. Keep in mind that Kissimmee holiday rental prices fluctuate throughout the year: the most expensive month to book is September, and the cheapest time to book is June.

  • Are there any Resort holiday rentals in Kissimmee?

    If you’re looking to book a Resort holiday rental in Kissimmee, then you have 346 to choose from. We recommend looking at Maingate Lakeside Resort as it’s currently the most popular Resort rental among our users.

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Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book the ones that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discounted hotels quickly, including Hotels Under $76 and Hotels Under $152. Discover hotel discounts now and make your hotel reservation today.