Vacation Rentals in Kissimmee

Start comparing over 4,128 rentals in Kissimmee and book at the best price!

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Vacation house
Vacation apartment
Pool
Internet
Balcony/Terrace
4.0
& up
4.5
& up

Best vacation rental deals in Kissimmee

7 nights
$1,684
$1,432
$204 / night
15% discount
Wed, 09/01 - Wed, 09/08
Vacation rental for 8 people, with pool
8 pers., 4 bedrooms, 1,905ft²
FREE cancellation
5.0
(2 reviews)
7 nights
$3,159
$2,946
$420 / night
7% discount
Wed, 08/11 - Wed, 08/18
Vacation rental for 12 people, with pool and jacuzzi
12 pers., 6 bedrooms, 2,045ft²
3.9
(10 reviews)
9 nights
$4,784
$3,674
$408 / night
23% discount
Fri, 08/13 - Sun, 08/22
Vacation rental for 10 people, with pool and terrace as well as jacuzzi
10 pers., 5 bedrooms
FREE cancellation
5.0

Vacation Rentals in Kissimmee
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from
$232
per night

Vacation rental for 20 people, with pool and garden as well as view
20 pers., 6 bedrooms
4.9
(7 reviews)

from
$232
per night

Vacation rental for 18 people, with terrace and pool as well as jacuzzi, child-friendly
18 pers., 6 bedrooms
4.0
(4 reviews)

from
$408
per night

Vacation rental for 18 people, with jacuzzi and garden as well as pool, with pets
18 pers., 8 bedrooms, 3,240ft²
FREE cancellation

from
$141
per night

Vacation rental for 6 people, with pool
6 pers., 3 bedrooms
FREE cancellation
3.9
(10 reviews)

from
$208
per night

Vacation rental for 12 people, with terrace and jacuzzi as well as pool, child-friendly
12 pers., 6 bedrooms

from
$151
per night

Vacation apartment for 10 people, with terrace and pool as well as lake view
10 pers., 4 bedrooms, 1,690ft²
3.9
(11 reviews)

from
$145
per night

Vacation rental for 6 people, with garden and pool
6 pers., 3 bedrooms
FREE cancellation

from
$221
per night

Vacation rental for 12 people, with pool and jacuzzi as well as garden
12 pers., 6 bedrooms, 2,497ft²
FREE cancellation

from
$239
per night

Vacation rental for 10 people, with terrace and view as well as pool
10 pers., 6 bedrooms
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Pet-friendly Vacation Rentals
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from
$122
per night

Vacation rental for 12 people, with pool and terrace, child-friendly
12 pers., 6 bedrooms, Pets allowed
3.5
(3 reviews)

from
$210
per night

Vacation rental for 12 people, with pets
12 pers., 6 bedrooms, Pets allowed

from
$334
per night

Vacation rental for 15 people, with pool and jacuzzi
15 pers., 5 bedrooms, Pets allowed
FREE cancellation
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Vacation Rentals with Pool
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from
$691
per night

Vacation rental for 32 people, with pool and jacuzzi as well as garden, with pets
32 pers., 15 bedrooms, 6,254ft²
FREE cancellation

from
$334
per night

Vacation rental for 12 people, with pool and jacuzzi as well as terrace
12 pers., 6 bedrooms
FREE cancellation

from
$165
per night

Vacation rental for 6 people, with garden and pool, child-friendly
6 pers., 3 bedrooms, 1,496ft²
FREE cancellation
4.7
(20 reviews)
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Vacation Rentals with Internet
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from
$237
per night

Vacation rental for 12 people, with pool and jacuzzi as well as garden
12 pers., 6 bedrooms, 2,594ft²
FREE cancellation
4.5
(7 reviews)

from
$155
per night

Vacation rental for 18 people, with pool and terrace, child-friendly
18 pers., 8 bedrooms
3.9
(5 reviews)

from
$215
per night

Vacation rental for 26 people, with terrace and jacuzzi as well as pool, child-friendly
26 pers., 11 bedrooms
3.1
(4 reviews)
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Vacation Rentals with Air Conditioning
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from
$393
per night

Vacation rental for 27 people, with terrace and pool
27 pers., 12 bedrooms
FREE cancellation
5.0
(2 reviews)

from
$58
per night

Vacation rental for 7 people, with pool and garden
7 pers., 3 bedrooms, 1,292ft²

from
$115
per night

Vacation rental for 8 people, with garden, child-friendly
8 pers., 3 bedrooms
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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 142
Internet 143
Balcony/Terrace 70
TV 141
Air conditioning 139
Garden 68

Other property types in Kissimmee that might be interesting:

Prices and availability

Prices

September
October
November
December
January
$437
Aug 07 - Aug 14
$353 per night
Aug 14 - Aug 21
$351 per night
Aug 21 - Aug 28
$324 per night
Aug 28 - Sep 04
$318 per night
Sep 04 - Sep 11
$324 per night
Sep 11 - Sep 18
$310 per night
Sep 18 - Sep 25
$312 per night
Sep 25 - Oct 02
$335 per night
Oct 02 - Oct 09
$321 per night
Oct 09 - Oct 16
$306 per night
Oct 16 - Oct 23
$323 per night
Oct 23 - Oct 30
$328 per night
Oct 30 - Nov 06
$316 per night
Nov 06 - Nov 13
$334 per night
Nov 13 - Nov 20
$355 per night
Nov 20 - Nov 27
$358 per night
Nov 27 - Dec 04
$371 per night
Dec 04 - Dec 11
$371 per night
Dec 11 - Dec 18
$380 per night
Dec 18 - Dec 25
$406 per night
Dec 25 - Jan 01
$437 per night
Jan 01 - Jan 08
$400 per night
Jan 08 - Jan 15
$328 per night
Jan 15 - Jan 22
$300 per night
Average price per week

Availabilities

September
October
November
December
January
63 %
Aug 07 - Aug 14
14 %
Aug 14 - Aug 21
26 %
Aug 21 - Aug 28
38 %
Aug 28 - Sep 04
40 %
Sep 04 - Sep 11
54 %
Sep 11 - Sep 18
54 %
Sep 18 - Sep 25
56 %
Sep 25 - Oct 02
47 %
Oct 02 - Oct 09
53 %
Oct 09 - Oct 16
43 %
Oct 16 - Oct 23
48 %
Oct 23 - Oct 30
46 %
Oct 30 - Nov 06
52 %
Nov 06 - Nov 13
54 %
Nov 13 - Nov 20
53 %
Nov 20 - Nov 27
36 %
Nov 27 - Dec 04
46 %
Dec 04 - Dec 11
63 %
Dec 11 - Dec 18
62 %
Dec 18 - Dec 25
39 %
Dec 25 - Jan 01
30 %
Jan 01 - Jan 08
41 %
Jan 08 - Jan 15
60 %
Jan 15 - Jan 22
59 %
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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