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Holiday 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 January (€82). Conversely, the most expensive month to stay in Kissimmee is March (€136).

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

The cheapest day to stay in Kissimmee is Monday (€94). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is €269.

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 €52 per night.
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Cheapest holiday 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 €150 per night. There is currently one property in Kissimmee that can be booked for this price. Reunion Resort & Golf Club is one of the hotels that can be booked for the lowest price in Kissimmee. Price data was last updated on 8 December 2025
Out of the holiday rentals in Kissimmee we've come across, these properties are priced the lowest. Prices will typically fluctuate depending on the dates selected, star rating of holiday rental, and holiday rental location.
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
€150
Avg. per night
View Deal

Other accommodations in Kissimmee

Find the perfect holiday rental for your stay in Kissimmee. There are 15,951 hotels in Kissimmee and price data was last updated on 8 December 2025. The average price for a hotel in Kissimmee is €109/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
€52
Avg. per night
View Deal
Westgate Vacation Villas Resort
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

7700 Westgate Boulevard, Kissimmee, FL, United States
17.7 km from city centre
Free Wi-Fi
Parking
€73
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
€97
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
€97
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
€284
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 December 2025.
Whether you're visiting Kissimmee for leisure or business, utilise the map to find holiday rentals close to your ideal location. As an added benefit, users can click a holiday rental they're interesting in to find helpful information and deals for that holiday rental.

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 December 2025.

  • How much does a holiday rental in Kissimmee cost?

    The average cost for a holiday rental in Kissimmee is €109/night. A good holiday rental deal in Kissimmee would be for €96/night or less. The cheapest rental deal found recently by our users was €26/night. If you’re flexible with your travel dates, then try to avoid booking November, the most expensive month of the year. Booking October is the cheapest month to book a holiday rental in Kissimmee.

  • 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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