Holiday rentals and lettings in Kissimmee

Holiday rentals and lettings in Kissimmee

Start comparing over 495 rentals in Kissimmee and book at the best price!

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Free cancellation
Holiday home
Holiday apartment
Pool
Internet
Pets allowed
4.0
& higher
4.5
& higher

Best holiday rental deals in Kissimmee

14 nights
£5,067
£4,473
£319 / night
12% discount
Sat, 07/05 - Sat, 21/05
Holiday rental for 16 people
16 pers.8 bedrooms450m²
FREE cancellation
3.3
(7 reviews)
8 nights
£1,505
£1,273
£159 / night
15% discount
Tue, 17/05 - Wed, 25/05
Holiday rental for 8 people
8 pers.4 bedrooms300m²
FREE cancellation
3.7
(21 reviews)
14 nights
£3,936
£3,680
£262 / night
7% discount
Wed, 02/02 - Wed, 16/02
Holiday rental for 13 people
13 pers.6 bedrooms340m²
FREE cancellation
3.6
(52 reviews)

Holiday Rentals with Free Cancellation

from
£125
per night
Holiday rental for 10 people, with pool
10 pers.4 bedrooms151m²
FREE cancellation
3.5
(9 reviews)
from
£82
per night
Holiday rental for 8 people, with pool
8 pers.4 bedrooms177m²
FREE cancellation
5.0
(2 reviews)
from
£668
per night
Holiday rental for 30 people, with pool
30 pers.16 bedrooms576m²
FREE cancellation
4.4
(8 reviews)
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Holiday Rentals & Lettings in Kissimmee

from
£304
per night
Holiday rental for 16 people, with pool
16 pers.9 bedrooms298m²
FREE cancellation
2.9
(4 reviews)
from
£295
per night
Holiday rental for 16 people, with pool
16 pers.6 bedrooms362m²
FREE cancellation
4.0
(21 reviews)
from
£114
per night
Holiday rental for 8 people, with pool
8 pers.4 bedrooms168m²
FREE cancellation
3.8
(2 reviews)
from
£127
per night
Holiday rental for 8 people, with pool
8 pers.4 bedrooms177m²
FREE cancellation
4.3
(84 reviews)
from
£161
per night
Holiday rental for 10 people, with pool
10 pers.4 bedrooms223m²
FREE cancellation
4.6
(8 reviews)
from
£131
per night
Holiday rental for 8 people, with pool
8 pers.4 bedrooms177m²
FREE cancellation
4.1
(9 reviews)
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Pet-friendly Holiday Rentals & Lettings

from
£106
per night
Holiday rental for 8 people
8 pers.4 bedrooms140m²
FREE cancellation
3.8
(3 reviews)
from
£134
per night
Holiday rental for 12 people, with pool, child-friendly
12 pers.5 bedrooms202m²
FREE cancellation
from
£113
per night
Holiday rental for 8 people, with pool, child-friendly
8 pers.3 bedrooms156m²
FREE cancellation
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Holiday Rentals & Lettings with Pool

from
£98
per night
Holiday rental for 8 people, with pool
8 pers.3 bedrooms
FREE cancellation
from
£127
per night
Holiday rental for 11 people, with pool
11 pers.4 bedrooms177m²
FREE cancellation
4.1
(7 reviews)
from
£174
per night
Holiday rental for 14 people, with pool and view
14 pers.5 bedrooms151m²
FREE cancellation
4.0
(10 reviews)
show all

Holiday Rentals & Lettings with Internet

from
£120
per night
Holiday rental for 10 people, with hot tub and terrace as well as pool
10 pers.5 bedrooms346m²
0.5
from
£145
per night
Holiday rental for 9 people, with pool
9 pers.4 bedrooms171m²
FREE cancellation
4.4
(2 reviews)
from
£135
per night
Holiday rental for 10 people, with pool
10 pers.4 bedrooms179m²
FREE cancellation
show all

Find Holiday Rentals & Lettings in Kissimmee

Map

Highlights in Kissimmee

  • Disney World
  • Family friendly
  • Everglades tours
  • Romantic holidays

Most popular in Kissimmee

Pool 238
Internet 245
Pets allowed 44
Balcony/Terrace 115
TV 243
Air conditioning 244

Other property types in Kissimmee that might be interesting:

Prices and availability

Prices

November
December
January
February
March
£288
Average price per week

Availabilities

November
December
January
February
March
53 %
Percentage of available lettings

Holiday rentals and lettings in Kissimmee

Lettings in the entertainment hub of the world

Home to Disney World, Kissimmee is one of the most popular holiday destinations in the world. But many people are pleasantly surprised by how much more there is to do here aside from the world-famous theme parks. There are thousands of holiday rentals to choose from in Kissimmee, all offering easy access to the theme parks. If you are looking for a holiday rental close to Kissimmee’s other attractions, search in the Old Town area of the city, which is crammed full of things to do for the whole family.

Luxurious lettings at a great price

There are few places in the world that offer villas of this quality. Opulent villas boasting private pools and spas, games and cinema rooms, and space for up to 20 people! And as an added bonus, the lettings are surprisingly well priced. Many holiday rentals offer spectacular golf course and lake views, guaranteeing a vacation that you will always hold close to your heart.

Holidays in Kissimmee

The area and getting around

Explore Santiago’s diverse barrios

Kissimmee is a short drive from Orlando, a major airport hub connected to every major country in the world. Effectively a suburb of Orlando, Kissimmee offers great value accommodation whilst putting you right on the doorstep of the world-famous Disney World theme parks. The city borders a huge lake to the south called Lake Tohopekaliga, a wonderful place for recreational activities.

Kissimmee – the apotheosis of the holiday experience

Verdant tropical landscapes create the ideal backdrop for outdoor adventures in and around Kissimmee. Whether you are zipping around the treetops, gliding through the Everglades, or soaring above it all in a hot air balloon, there are thrills-a-penny in this holiday paradise. Natural landscapes transform into quaint downtown areas where you can embark on boutique shopping and local dining, and explore lakeside parks. At Kissimmee you will achieve a state of pure holiday nirvana in a city where thrill meets chill!

Travellers and activities

Kissimmee for romantic holidays

Couples come to Kissimmee from all over the world to experience horseback riding at Hidden Palms Ranch, clear kayak tours in the scenic canals linking Lake Virginia and Lake Osceola, hot air balloon rides over central Florida’s diverse landscape, walks hand in the beautiful Leu Gardens, performances at the Dr. Phillips Center for the Performing Arts.. and so on, and so on. There are literally a hundred holidays to be had in Kissimmee for couples, so if you haven’t come yet, make this your first time!

Kissimmee for Disney fans

There are four theme parks at Walt Disney World where you will forge memories of a lifetime. Magic Kingdom, home to the iconic Cinderella Castle, is a magical theme park with rollercoasters, carousels, 4D cinemas and the like. Epcot, which means Experimental Prototype Community of Tomorrow, has two main sections, Future World, which fuses learning with entertainment in spellbinding pavilions where your imagination is encouraged to run riot, and World Showcase, which provides a fascinating taste of 11 countries in miniature. Disney's Hollywood Studios is home to unforgettable rides and shows based on films such as Star Wars and Indiana Jones. Last but not least, Disney's Animal Kingdom is a fun-fuelled concoction of live animals such as tigers, elephants and rhinos and traditional rides and shows. The million-dollar question is where to start?!

„Kissimmee is a place where’s childhood memories are set in stone, with the greatest collection of theme parks in the world!“

Top 5 travel tips in Kissimmee

1. Take a day trip to the sea

Daytona beach on the Atlantic is the closest beach to Kissimmee, just 1.5 hours away by car. This lovely beach entices visitors to its family-friendly activities and outdoor activities such as parasailing, kayaking, and eco-boat tours.

2. Get close up to Florida’s most notorious inhabitant

Gatorland is the area’s most highly-rated gator park, with knowledgeable guides, an aviary, a small zoo where you can touch the animals, various animal shows and a natural alligator farm. Don’t miss the spectacular feeding show where crocs jump high out of the water!

3. Take a swamp boat tour of the Everglade!

Explore "real Florida" on a swamp boat: a trip on the famed Everglades swamps on a boat powered by an aircraft-type propeller is a must-do activity for visitors to Kissimmee. For the best views, book a sunset tour.

4. Shake hands with Florida’s greatest sports stars

Florida Sports Hall of Fame displays many of the notable Floridian sports celebrities with waxwork models of internationally renowned sports legends such as Jack Nicklaus, Chris Evert, and Otis Birdsong. Amazingly, it's free to get in!

5. Take a fossil hunting tour

Fossil Funatics is an outdoor adventure into ancient times. The central Florida Waterways are a mecca for fossil lovers who come for daylong tours which provide you with everything you need to embark on a fun fossil hunting expedition!

FAQs: Holiday Rentals & Lettings in Kissimmee

How much does it cost to book a holiday rental in Kissimmee?

Based on its annual average price of £236.35, Kissimmee is not a city that stands out for being the most expensive or the cheapest in the USA.

When are holiday rentals cheaper in Kissimmee?

According to our most recent historical data, the months with the cheapest prices in Kissimmee are May, November, and August, with average prices of £219.53, £219.68 and £220.2, respectively.

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

In 2020, the month that offered the highest average prices in Kissimmee was March, with an average price of £267.97 per night. This was followed by February, with an average of £258.49, and April, with £257.51.

Is Kissimmee a good location for a spontaneous getaway?

If you decide to discover Kissimmee, we suggest planning your travels in advance because it tends to be very high in demand, with an annual average occupation of 59% in the year 2020.

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

May, September, and August are, in order of highest to lowest, the months offering the largest number of accommodations free, with respective average availability figures of 54.4%, 53.5% and 52.6%.

When are fewer lettings available?

The month with the highest average booked rental figures is February (only 9.2% of properties were available on average in 2019). Followed by March (20.75%), and January (22.5%).

Are there many holiday rentals in Kissimmee?

In Kissimmee we have an extensive catalogue of approximately 3500 properties, with options to suit everyone, thanks to our 13 local and international partners.

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

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