Vacation Rentals in Kissimmee

Vacation Rentals in Kissimmee

Start comparing over 210 rentals in Kissimmee and book at the best price!

Find offers

Vacation house
Vacation apartment
Pool
Internet
Pets allowed
4.0
 & higher
Free cancellation

Vacation Rentals in Kissimmee

Vacation rental for 8 people, with pool in Kissimmee
Vacation rental for 8 people, with pool
4 bedrooms
4.1
(22 reviews)
from $153 / nightFREE cancellation
Vacation rental for 8 people, with pool in Kissimmee
Vacation rental for 8 people, with pool
4 bedrooms
3.4
(5 reviews)
from $133 / nightFREE cancellation
Vacation rental for 10 people, with terrace and lake view as well as pool in Kissimmee
Vacation rental for 10 people, with terrace and lake view as well as pool
5 bedrooms
2.2
(4 reviews)
from $165 / night
Vacation rental for 10 people, with pool in Kissimmee
Vacation rental for 10 people, with pool
4 bedrooms
3.6
(16 reviews)
from $218 / nightFREE cancellation

Popular Vacation Rentals in Kissimmee

Vacation rental for 12 people, with pool and lake view as well as terrace in Kissimmee
Vacation rental for 12 people, with pool and lake view as well as terrace
6 bedrooms
3.4
(6 reviews)
from $189 / night
Vacation rental for 8 people, with yard and hot tub as well as pool in Kissimmee
Vacation rental for 8 people, with yard and hot tub as well as pool
4 bedrooms
4.7
(16 reviews)
from $98 / night
Vacation rental for 8 people, with pool in Kissimmee
Vacation rental for 8 people, with pool
4 bedrooms
4.2
(18 reviews)
from $148 / nightFREE cancellation
Vacation apartment for 6 people, with terrace and lake view as well as pool in Kissimmee
Vacation apartment for 6 people, with terrace and lake view as well as pool
3 bedrooms
3.4
(3 reviews)
from $80 / night

Vacation rentals with free cancellation

Vacation rental for 25 people, with pool in Kissimmee
Vacation rental for 25 people, with pool
9 bedrooms
from $691 / nightFREE cancellation
Vacation rental for 12 people, with balcony/terrace and pool as well as balcony in Kissimmee
Vacation rental for 12 people, with balcony/terrace and pool as well as balcony
6 bedrooms
4.0
from $233 / nightFREE cancellation
Vacation rental for 8 people, with yard and pool in Kissimmee
Vacation rental for 8 people, with yard and pool
4 bedrooms
2.5
(2 reviews)
from $166 / nightFREE cancellation
Vacation rental for 20 people, with pool in Kissimmee
Vacation rental for 20 people, with pool
9 bedrooms
from $494 / nightFREE cancellation

Pet-friendly Vacation Rentals

Vacation rental for 10 people, with pool and terrace as well as hot tub, with pets in Kissimmee
Pet allowed
Vacation rental for 10 people, with pool and terrace as well as hot tub, with pets
5 bedrooms
4.3
(12 reviews)
from $126 / night
Vacation rental for 8 people, with pool and view as well as terrace in Kissimmee
Pet allowed
Vacation rental for 8 people, with pool and view as well as terrace
4 bedrooms
from $117 / nightFREE cancellation
Vacation rental for 10 people, with pool and terrace, kid friendly in Kissimmee
Pet allowed
Vacation rental for 10 people, with pool and terrace, kid friendly
5 bedrooms
4.1
(26 reviews)
from $157 / night
Vacation rental for 12 people, with terrace and pool, kid friendly in Kissimmee
Pet allowed
Vacation rental for 12 people, with terrace and pool, kid friendly
6 bedrooms
4.2
(14 reviews)
from $154 / night

Vacation Rentals with Pool

Vacation rental for 10 people, with pool in Kissimmee
Pool
Vacation rental for 10 people, with pool
4 bedrooms
3.2
(4 reviews)
from $218 / nightFREE cancellation
Vacation rental for 16 people, with lake view and terrace as well as pool in Kissimmee
Pool
Vacation rental for 16 people, with lake view and terrace as well as pool
8 bedrooms
4.0
from $243 / night
Vacation rental for 8 people, with pool in Kissimmee
Pool
Vacation rental for 8 people, with pool
4 bedrooms
4.5
(9 reviews)
from $136 / nightFREE cancellation
Vacation rental for 6 people, with pool and yard in Kissimmee
Pool
Vacation rental for 6 people, with pool and yard
3 bedrooms
from $131 / nightFREE cancellation

Vacation Rentals with Internet

Vacation rental for 14 people, with pool, kid friendly in Kissimmee
Internet
Vacation rental for 14 people, with pool, kid friendly
6 bedrooms
from $229 / nightFREE cancellation
Vacation rental for 10 people, with pool in Kissimmee
Internet
Vacation rental for 10 people, with pool
3 bedrooms
3.0
(5 reviews)
from $143 / nightFREE cancellation
Vacation rental for 8 people, with pool in Kissimmee
Internet
Vacation rental for 8 people, with pool
4 bedrooms
from $136 / nightFREE cancellation
Vacation apartment for 10 people, with lake view and pool as well as terrace in Kissimmee
Internet
Vacation apartment for 10 people, with lake view and pool as well as terrace
4 bedrooms
from $103 / night

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

Best vacation rentals in Kissimmee

Guests agree: these stays are highly rated for location, cleanliness, and more.
more...
Kissimmee, Osceola County
Vacation Rental • 2400 ft² • 4 Bedrooms
4.3
(2 reviews)
Beautiful vacation home in Sonoma Resort. A brand-new vacation rental resort located just 10 minutes from Disney parks, upscale brand outlets and more. The resort Sonoma offers exceptional amenities, including a luxury clubhouse, cabanas, resort-style pool, and high-speed internet. These 4 bedrooms and 3 bathrooms home can comfortably accommodate up to 10 people.The SpaceBeing a one floor home makes this the ideal space for families with younger kids or elderly. Open kitchen concept with cozy living room makes it the perfect place for your family to gather. Fully furnished kitchen with plen...
from $218 / night
more...
Kissimmee, Osceola County
Vacation Rental • 4306 ft² • 7 Bedrooms
4.2
(22 reviews)
This amazing 7-bedroom home, with 6.5 bathrooms, is conveniently located in Sonoma Resort, a brand-new vacation rental resort just 10 minutes from Disney parks, upscale brand outlets and more. Featuring 7 bedrooms and 6.5 bathrooms is a perfect fit for families and friends traveling together.The SpaceThis beautifully decorated home can accommodate up to 18 people comfortably. This home is tastefully decorated with modern furniture in earth tones that are inviting and warm. The open kitchen concept features a fully equipped kitchen with stainless steel appliances and granite countertops, all...
from $451 / night
more...
Kissimmee, Osceola County
Vacation Apartment • 1894 ft² • 4 Bedrooms
3.9
(32 reviews)
Experience what a vacation home in Orlando is all about!Bella Vida Resort offers great amenities and facilities including: a spacious lounge, movie theatre, cyber cafe, fitness center, basketball court, sand volleyball court, resort pool and spa, and tot lot. It is a great opportunity to spend an affordable time with family and kids when the attraction parks are not in the program for the day!Bella Vida Resort has immediate access to US 192, nearby there are convenience and grocery stores, thematic restaurants such as Medieval Times, Capone, and many other places and nature trails to explor...
from $108 / night

Most popular in Kissimmee

Pool 1,258
Internet 563
Pets allowed 94
Balcony/Terrace 189
TV 544
Air conditioning 561

Other property types in Kissimmee that might be interesting:

Prices and availability

Vacation rental prices Kissimmee

$318for 8 Oct - 15 Oct
$358 annual average
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Average price per week

Vacation rentals availability Kissimmee

24%for 8 Oct - 15 Oct
54% annual average
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
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.

Booking.com Vacation Rentals in KissimmeeBooking.com Vacation Rentals in Kissimmee
Airbnb Vacation Rentals in KissimmeeAirbnb Vacation Rentals in Kissimmee
Vrbo Vacation Rentals in KissimmeeVrbo Vacation Rentals in Kissimmee
Bookiply Vacation Rentals in KissimmeeBookiply Vacation Rentals in Kissimmee
FeWo-direkt Vacation Rentals in KissimmeeFeWo-direkt Vacation Rentals in Kissimmee
Abritel Vacation Rentals in KissimmeeAbritel Vacation Rentals in Kissimmee
HRS Vacation Rentals in KissimmeeHRS Vacation Rentals in Kissimmee
500+ more
  1. Vacation Rentals
  2. USA
  3. Florida
  4. Disney Orlando
  5. Central Florida
  6. Kissimmee