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Vacation rentals in Kissimmee

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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 May ($80). Conversely, the most expensive month to stay in Kissimmee is June ($252).

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

The cheapest day to stay in Kissimmee is Sunday ($90). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $122.

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

Save money by booking a vacation rental at least 40 days before your trip to Kissimmee. The lowest price found when booking 40 days ahead was $55 per night.

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Cheapest vacation rentals in Kissimmee, Florida

These Kissimmee properties charge the lowest price per night of those we've come across. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
Vacation Village at Parkway
Vacation Village at Parkway

Vacation Village at Parkway

2975 Arabian Nights Boulevard, Kissimmee, FL, United States
7.3 mi from city centre
$67
Avg. per night
View Deal
Westgate Vacation Villas Resort
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

7700 Westgate Boulevard, Kissimmee, FL, United States
11.0 mi from city centre
Free Wi-Fi
Parking
$90
Avg. per night
View Deal
Reunion Resort & Golf Club
Reunion Resort & Golf Club

Reunion Resort & Golf Club

7593 Gathering Drive, Kissimmee, FL, United States
10.7 mi from city centre
Free Wi-Fi
$189
Avg. per night
View Deal
Berkley Lake Townhomes
Berkley Lake Townhomes

Berkley Lake Townhomes

1010 Park Ridge Circle, Kissimmee, FL, United States
3.2 mi from city centre
Free Wi-Fi
$201
Avg. per night
View Deal
Margaritaville Cottages Orlando by Rentyl
Margaritaville Cottages Orlando by Rentyl

Margaritaville Cottages Orlando by Rentyl

8000 Fins Up Circle, Kissimmee, FL, United States
12.0 mi from city centre
Free Wi-Fi
Parking
$211
Avg. per night
View Deal

Other accommodations in Kissimmee

Palazzo Lakeside Hotel Kissimmee
Palazzo Lakeside Hotel Kissimmee

Palazzo Lakeside Hotel Kissimmee

4944 West Irlo Bronson Memorial Highway, Kissimmee, FL, United States
4.3 mi 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
11.0 mi from city centre
Free Wi-Fi
Parking
$90
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
7.1 mi from city centre
Free Wi-Fi
$321
Avg. per night
View Deal

Where to stay in Kissimmee

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

  • How much does a vacation rental in Kissimmee cost?

    $117 per night is how much a vacation rental in Kissimmee costs, on average. $31 per night was the cheapest price recently found by our users, though anything for $98 per night or less is a good deal. Keep in mind that Kissimmee vacation rental prices fluctuate throughout the year: the most expensive month to book is August, and the cheapest time to book is March.

  • What is the best Kissimmee vacation rental?

    Vacation Village Orlando, Celebration has a 8.5 rating from 3,057 users, making it the best Kissimmee vacation rental based on our data.

  • What’s the closest vacation rental to Orlando Airport?

    It’s only 15.1 mi from Orlando Airport to Vacation Village Orlando, Celebration (the nearest Kissimmee vacation rental to the airport).

  • What part of Kissimmee is best to stay in?

    The best neighborhood to stay in Kissimmee is Downtown, according to our user data. 58% of our users who looked for vacation rentals in Kissimmee searched for properties in the Downtown area. If you’re also interested in booking a vacation rental in Downtown, consider the 1 BD Apt close to Disney/Universal/Shopping/Dining - the neighborhood’s most popular rental property.

  • Are there Kissimmee vacation rentals with “Pool” listed as an amenity?

    2 vacation rentals in Kissimmee currently mention “Pool” as a listed amenity. We recommend booking the Vacation Village Orlando, Celebration, which is the most popular Kissimmee vacation rental featuring this amenity.

  • Are there any Resort vacation rentals in Kissimmee?

    At the moment, there are 558 properties listed as a Resort vacation rental in Kissimmee. A popular Resort in Kissimmee amongst our users is Magic Moment Resort And Kids Club.

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