Vacation Rentals in Kissimmee

Vacation Rentals in Kissimmee

Start comparing over 658 rentals in Kissimmee and book at the best price!

Find Vacation Rentals in Kissimmee

Highlights Kissimmee

  • Walt Disney World Resort
  • At 15 meters height through the trees of Florida in the Orlando Tree Trek
  • Swamp boat tours
  • Excursion to the sea

Best Vacation Rentals in Kissimmee

Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation Rental for 8 Guests in Kissimmee, Osceola County
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Kissimmee, Osceola County
Vacation Rental • 1378 ft² • 3 Bedrooms
10.0
(25 reviews)
This charming 3 bedroom, southwest-facing villa is on the Indian Point community in Kissimmee. Just off the US192 with its incredible range of shops, bars & restaurants to suit all. The Disney parks are 15 min drive away, with Universal Studios slightly further, needing a 25 min trip. Back at the villa, sun worshippers are well catered for with the pool deck which has fencing to all sides, giving you extra privacy as you soak up the sun, or dine alfresco, making use of the outside dining area.The home and pool are professionally managed and maintained, ensuring your stay is worry-free--...
from $104 / night
Vacation Rental for 12 Guests in Kissimmee, Osceola County
Vacation Rental for 12 Guests in Kissimmee, Osceola County, Picture 1
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Kissimmee, Osceola County
Vacation Rental • 12 Guests • 6 Bedrooms
7.4
(7 reviews)
This is a superb secluded large villa in the popular gated community of Cumbrian Lakes. The home boasts of a magnificent view to have your Self Catering Vacation in. The Large Pool and Spa is lakefront and overlooks a lush conservation area. This is, therefore, a wonderful spot to relax in the pool or spa and totally unwind. The home itself has 6 bedrooms five of which have TVs. There are also three and a half bathrooms. The upper level has an oversized master bedroom where you can luxuriate in the king-sized four-poster bed. You may also want to enjoy some hard-earned peace and quiet sitti...
from $230 / night
Vacation Rental for 12 Guests in Kissimmee, Osceola County
Vacation Rental for 12 Guests in Kissimmee, Osceola County, Picture 1
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Kissimmee, Osceola County
Vacation Rental • 3509 ft² • 6 Bedrooms
9.9
(42 reviews)
If you are looking for an amazing value to get away for vacation, this well-kept home is the fun and relaxing getaway you need.Property Overview• Beautiful lake views from the large pool deck and relaxing pool with spa• Outdoor kitchenette with complimentary BBQ• Fun filled games room• Fully equipped kitchen• Air conditioning and indoor ceiling fans• FREE WiFi• Towels and linens provided• FREE use of pack 'n' play and high chair• Laundry room with full-size washer and dryer• Professionally managed by White Rose Villas to offer you a superior, personalized service• Express check-in. No key p...
from $185 / night

Other holiday ideas and property types in Kissimmee that might be interesting

Prices and availability

Current Vacation rental prices Kissimmee

$319for 2 Dec - 9 Dec
$370 annual average
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Average price per week

Current vacation rental availability Kissimmee

48%for 2 Dec - 9 Dec
54% annual average
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Percentage of available rentals

Vacation rentals in Kissimmee

Nature and action in Kissimmee

Kissimmee is a quiet town near Orlando in Florida. Best conditions for a huge selection of holiday accommodations. A vacation home? How about a Lakeside villa with private pool and rowing boat mooring? Or would you prefer a luxury holiday apartment or a chic apartment with great shopping possibilities around you? Because of its proximity to Disney World you will find in Kissimmee everything your heart desires!

Holiday in Kissimmee

Location and orientation

Holidays at Disney-World

The city of Kissimmee is only 25 km away from the capital of Florida, Orlando - and therefore close to the huge Disney World Resort forest and many other amusement parks. And although the Metropolitan Area is so close, Kissimmee has been able to preserve its beautiful nature - including the legendary Florida marshes. The sea is about 2.5 hours away by car, but most vacation rentals have their own pool.

Due to the many amusement parks nearby, there are a number of (mostly free) shuttle buses, so you can leave your car comfortably at home.

Top 3 travel tips

1st Walt Disney World Resort

What would a holiday in a vacation rental in Kissimmee be without a visit to the legendary Disney World? Here everything revolves around Mickey and Co, the biggest blockbusters and lots of crazy roller coasters. From the water park over the Wild West Area, up to breathtaking shows. Immerse yourself in the colourful world of all-round entertainment.

2. The Orlando Tree Trek

A very special nature experience awaits you on the Orlando Tree Trek. It winds its way through the trees of Florida in airy heights of up to 15 metres over 97 different "stations". While most of the time you walk over wooden footbridges and suspension bridge constructions, the trek also includes sections where you whiz through the air with the Tarzan slides and cable cars.

3. A marsh boat trip through the marshes

Kissimmee borders on the northern Everglades, the legendary swamp and marsh area of Florida. The best way to admire this impenetrable region is to take a swamp boat tour. This can get very loud (protective headphones are provided), but with a bit of luck you can see alligators, flamingos, eagles, wild boars and lots of amphibians and snakes in their natural environment.

FAQs: Vacation Rentals in Kissimmee

On average, what was the cost for vacation rentals in Kissimmee last year?

Based on last year, Kissimmee had an average price of $350 per night, a relatively high one compared to the cities in the USA.

During which months can you find the best price for vacation rentals in Kissimmee?

]If you want to get the most out of your money, the most budget-friendly months to visit Kissimmee are May ($305 the average per night for accommodation), June ($319), and September ($333).

When does the price of vacation rentals in Kissimmee go up the most?

When it comes to looking for a vacation rental in Kissimmee, the months that cost the most are, in order of highest to lowest, December, March and February, with average prices per night of $409, $375, and $373, respectively.

Do I need to plan a trip to Kissimmee well in advance?

It is better to book sooner than later in Kissimmee as only 25% of the accommodations remain available throughout the year, according to last year's data.

What time of the year can I find more available vacation rentals?

Last year, the months with the most vacation rentals available of the year in Kissimmee were May, June and September, with average availabilities of 53%, 50%, and 36%, respectively.

During which months is it more difficult to find available vacation rentals?

The month with the highest average booked rental figures is February (only 7% of properties were available on average last year). Followed by March (7%), and then July (15%). During these three months, the availability is very low (9%). It is therefore recommended to reserve far in advance.

How many rentals does Holidu have in Kissimmee?

We have grouped together the offers from 20 different providers in Kissimmee, so we can offer you around 1,400 properties. You're going to have a hard time choosing your favorite!

Holidu compares hundreds of websites to find your perfect holiday rental for the best price.

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