Vacation Rentals in Kissimmee

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Popular Accommodations in Kissimmee

from
$114
per night

Vacation rental for 10 people
10 pers., 1 bedroom
5.0

from
$179
per night

Vacation rental for 10 people, with pool
10 pers., 4 bedrooms, 2,400ft²FREE cancellation
4.4
(8 reviews)

from
$179
per night

Vacation rental for 8 people, with pool
8 pers., 4 bedrooms, 2,400ft²FREE cancellation
4.0
(13 reviews)
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Vacation rentals with free cancellation
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from
$156
per night

Apartment for 6 people, with pool
6 pers., 2 bedrooms, 1,195ft²FREE cancellation
4.3
(456 reviews)

from
$117
per night

Vacation rental for 8 people, with pool
8 pers., 4 bedrooms, 1,485ft²FREE cancellation

from
$161
per night

Vacation rental for 10 people, with pool
10 pers., 4 bedrooms, 1,905ft²FREE cancellation
3.4
(3 reviews)
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Vacation Rentals in Kissimmee
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from
$179
per night

Vacation rental for 11 people, with pool
11 pers., 4 bedrooms, 1,905ft²FREE cancellation
4.6
(6 reviews)

from
$429
per night

Vacation rental for 16 people, with pool
16 pers., 8 bedrooms, 3,208ft²FREE cancellation
2.9
(4 reviews)

from
$157
per night

Vacation rental for 8 people, with pool
8 pers., 4 bedrooms, 1,905ft²FREE cancellation
4.2
(6 reviews)

from
$269
per night

Vacation rental for 20 people, with garden and jacuzzi as well as pool, child-friendly
20 pers., 7 bedroomsFREE cancellation
4.1
(17 reviews)

from
$95
per night

Apartment for 8 people, with jacuzzi and pool
8 pers., 3 bedrooms, 1,195ft²FREE cancellation

from
$106
per night

Vacation rental for 14 people, with jacuzzi and pool
14 pers., 4 bedrooms, 1,873ft²FREE cancellation
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Pet-friendly Vacation Rentals
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from
$111
per night

Vacation rental for 6 people, with jacuzzi
6 pers., 3 bedrooms, 1,281ft²FREE cancellation

from
$76
per night

Apartment for 6 people, with pool and garden, child-friendly
6 pers., 3 bedrooms
0.8
(2 reviews)

from
$177
per night

Vacation rental for 8 people, with view and pool
8 pers., 4 bedrooms, 1,905ft²
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Vacation Rentals with Pool
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from
$417
per night

Vacation rental for 12 people, with pool
12 pers., 4 bedrooms, 151ft²FREE cancellation

from
$417
per night

Vacation rental for 13 people, with pool
13 pers., 6 bedrooms, 3,800ft²FREE cancellation
5.0

from
$375
per night

Vacation rental for 17 people, with pool
17 pers., 8 bedrooms, 3,208ft²FREE cancellation
4.4
(2 reviews)
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Vacation Rentals with Internet
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from
$300
per night

Vacation rental for 12 people, with pool
12 pers., 6 bedrooms, 2,809ft²FREE cancellation
3.7
(12 reviews)

from
$185
per night

Vacation rental for 15 people, with pool
15 pers., 5 bedrooms, 2,110ft²FREE cancellation
3.8

from
$154
per night

Vacation rental for 10 people, with pool
10 pers., 4 bedrooms, 1,927ft²
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Find Vacation Rentals in Kissimmee

Map

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

Most popular in Kissimmee

Pool 117
Internet 118
Balcony/Terrace 39
TV 115
Air conditioning 119
Parking 117
Washing machine 114
Jacuzzi 43
Heating 87

Other property types in Kissimmee that might be interesting:

Prices and availability

Prices

May
June
July
August
September
$358
Apr 03 - Apr 10
$358 per night
Apr 10 - Apr 17
$339 per night
Apr 17 - Apr 24
$313 per night
Apr 24 - May 01
$296 per night
May 01 - May 08
$284 per night
May 08 - May 15
$284 per night
May 15 - May 22
$306 per night
May 22 - May 29
$323 per night
May 29 - Jun 05
$321 per night
Jun 05 - Jun 12
$319 per night
Jun 12 - Jun 19
$323 per night
Jun 19 - Jun 26
$329 per night
Jun 26 - Jul 03
$337 per night
Jul 03 - Jul 10
$341 per night
Jul 10 - Jul 17
$330 per night
Jul 17 - Jul 24
$330 per night
Jul 24 - Jul 31
$327 per night
Jul 31 - Aug 07
$323 per night
Aug 07 - Aug 14
$347 per night
Aug 14 - Aug 21
$345 per night
Aug 21 - Aug 28
$311 per night
Aug 28 - Sep 04
$311 per night
Sep 04 - Sep 11
$318 per night
Sep 11 - Sep 18
$299 per night
Average price per week

Availabilities

May
June
July
August
September
67 %
Apr 03 - Apr 10
30 %
Apr 10 - Apr 17
38 %
Apr 17 - Apr 24
46 %
Apr 24 - May 01
37 %
May 01 - May 08
57 %
May 08 - May 15
55 %
May 15 - May 22
55 %
May 22 - May 29
50 %
May 29 - Jun 05
51 %
Jun 05 - Jun 12
48 %
Jun 12 - Jun 19
52 %
Jun 19 - Jun 26
48 %
Jun 26 - Jul 03
45 %
Jul 03 - Jul 10
54 %
Jul 10 - Jul 17
55 %
Jul 17 - Jul 24
54 %
Jul 24 - Jul 31
56 %
Jul 31 - Aug 07
59 %
Aug 07 - Aug 14
64 %
Aug 14 - Aug 21
61 %
Aug 21 - Aug 28
67 %
Aug 28 - Sep 04
64 %
Sep 04 - Sep 11
65 %
Sep 11 - Sep 18
65 %
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

What was the average price for a vacation rental in Kissimmee in 2020, during the corona crisis?

Kissimmee is one of the cheapest cities in the USA. The costs for a vacation rental here amount to around $328.71 per night.

During which months are vacation rentals cheaper in Kissimmee?

According to our most recent data, the months that allow you to save the most in Kissimmee are May, November and August, with average prices of $305.32, $305.53, and $306.25, respectively.

When are vacation rentals more expensive in Kissimmee?

When it comes to looking for a vacation rental in Kissimmee, the most expensive months are, in order of highest to lowest, March, February and April, with average prices per night of $372.7, $359.51, and $358.14, respectively.

Is it necessary to plan a trip to Kissimmee well in advance?

If you decide to put Kissimmee on your bucket list, we recommend planning your travels long before you go because it is usually very high in demand, with an annual average of 59% of rentals booked in the year 2020.

When are more vacation rentals available?

In 2020, the months with the largest number of accommodations available of the year in Kissimmee were May, September and August, with average availabilities of 54.4%, 53.5%, and 52.6%, respectively.

Which months is it more difficult to find available vacation rentals?

The months with the lowest properties available in Kissimmee are, in order, February, March, and January with respective average availability figures of 9.2%, 20.75%, and 22.5%, based on data collected in 2020.

How many vacation rentals are there in Kissimmee?

In Kissimmee we work with 13 different providers to give you a choice of 3600 properties, so you will not be short of options!

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

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