Vacation Rentals & Apartments in Kissimmee

Vacation Rentals & Apartments in Kissimmee

Start comparing over 296 rentals in Kissimmee and book at the best price!

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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
3 bedrooms
3.5
(2 reviews)
from CA$130 / nightFREE cancellation
Vacation rental for 8 people, with pool in Kissimmee
Vacation rental for 8 people, with pool
4 bedrooms
4.4
(11 reviews)
from CA$183 / nightFREE cancellation
Vacation rental for 6 people, with pool and lake view as well as terrace in Kissimmee
Vacation rental for 6 people, with pool and lake view as well as terrace
3 bedrooms
3.4
(3 reviews)
from CA$107 / night
Vacation rental for 8 people, with pool in Kissimmee
Vacation rental for 8 people, with pool
4 bedrooms
4.3
(18 reviews)
from CA$197 / nightFREE cancellation

Popular Vacation Rentals and Apartments in Kissimmee

Vacation rental for 8 people in Kissimmee
Vacation rental for 8 people
3 bedrooms
from CA$197 / nightFREE cancellation
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
3.6
(7 reviews)
from CA$254 / night
Vacation rental for 10 people, with balcony/terrace in Kissimmee
Vacation rental for 10 people, with balcony/terrace
5 bedrooms
4.2
(15 reviews)
from CA$238 / nightFREE cancellation
Vacation rental for 14 people in Kissimmee
Vacation rental for 14 people
6 bedrooms
4.0
(5 reviews)
from CA$204 / nightFREE cancellation

Vacation rentals with free cancellation

Vacation rental for 14 people, with pool, child-friendly in Kissimmee
Vacation rental for 14 people, with pool, child-friendly
6 bedrooms
from CA$309 / nightFREE cancellation
Vacation rental for 10 people, with pool in Kissimmee
Vacation rental for 10 people, with pool
3 bedrooms
from CA$191 / nightFREE cancellation
Vacation rental for 8 people, with pool in Kissimmee
Vacation rental for 8 people, with pool
4 bedrooms
from CA$182 / nightFREE cancellation
Vacation rental for 6 people, with pool, child-friendly in Kissimmee
Vacation rental for 6 people, with pool, child-friendly
3 bedrooms
from CA$175 / nightFREE cancellation

Holiday Rentals & Lettings with Pool

Vacation rental for 10 people, with pool in Kissimmee
Pool
Vacation rental for 10 people, with pool
4 bedrooms
3.6
(16 reviews)
from CA$291 / nightFREE cancellation
Vacation rental for 12 people, with pool in Kissimmee
Pool
Vacation rental for 12 people, with pool
6 bedrooms
5.0
(20 reviews)
from CA$244 / nightFREE cancellation
Vacation rental for 11 people, with pool in Kissimmee
Pool
Vacation rental for 11 people, with pool
4 bedrooms
4.0
(17 reviews)
from CA$197 / nightFREE cancellation
Vacation rental for 8 people, with pool in Kissimmee
Pool
Vacation rental for 8 people, with pool
3 bedrooms
4.8
(20 reviews)
from CA$151 / nightFREE cancellation

Pet-friendly Holiday Rentals & Lettings

Vacation rental for 10 people, with pool and terrace, child-friendly in Kissimmee
Pet allowed
Vacation rental for 10 people, with pool and terrace, child-friendly
5 bedrooms
4.1
(26 reviews)
from CA$201 / night
Vacation rental for 8 people, with lake view and pool in Kissimmee
Pet allowed
Vacation rental for 8 people, with lake view and pool
4 bedrooms
4.9
(13 reviews)
from CA$174 / night
Vacation rental for 6 people, with pool and hot tub as well as garden in Kissimmee
Pet allowed
Vacation rental for 6 people, with pool and hot tub as well as garden
3 bedrooms
4.5
(4 reviews)
from CA$162 / night
Vacation rental for 10 people, with hot tub and pool as well as terrace, with pets in Kissimmee
Pet allowed
Vacation rental for 10 people, with hot tub and pool as well as terrace, with pets
3 bedrooms
4.6
(6 reviews)
from CA$633 / night

Holiday Rentals & Lettings with Internet

Vacation rental for 4 people in Kissimmee
Internet
Vacation rental for 4 people
1 bedroom
2.5
(7 reviews)
from CA$116 / night
Vacation rental for 6 people, with garden and pool in Kissimmee
Internet
Vacation rental for 6 people, with garden and pool
4 bedrooms
4.5
(42 reviews)
from CA$157 / night
Vacation rental for 6 people, with garden and pool in Kissimmee
Internet
Vacation rental for 6 people, with garden and pool
3 bedrooms
from CA$175 / nightFREE cancellation
Vacation rental for 18 people, with pool in Kissimmee
Internet
Vacation rental for 18 people, with pool
7 bedrooms
4.2
(21 reviews)
from CA$602 / nightFREE cancellation

Find Vacation Rentals and Apartments in Kissimmee

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Highlights Kissimmee

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

Best vacation rentals in Kissimmee

Guests agree: these stays are highly rated for location, cleanliness, and more.
more...
Kissimmee, Osceola County
Vacation Rental • 177 m² • 4 Bedrooms
4.0
(17 reviews)
One of the newest and best-located resort communities in the Orlando area with stunning amenities, Storey Lake Resort has it all! Located next to Walt Disney World and central to Orlando's world-class attractions, it is the perfect place for your ideal vacation. You will love this 4-bedroom, 3-bathrooms townhome, which accommodates up to 11 people. It offers stainless steel appliances, a luxurious granite countertop and state-of-the-art cabinets. For the total comfort of our guests, the kitchen is fully equipped with pots and pans. Seasoning items are not provided for the safety reasons of ...
from CA$197 / night
more...
Kissimmee, Osceola County
Vacation Rental • 176 m² • 4 Bedrooms
4.0
(34 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 CA$144 / night
more...
Kissimmee, Osceola County
Vacation Rental • 223 m² • 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 CA$291 / night

Most popular in Kissimmee

Pool 1,636
Internet 758
Pets allowed 138
Balcony/Terrace 198
TV 701
Air conditioning 754

Prices and availability

Vacation rental prices Kissimmee

CA$422for 1 Oct - 8 Oct
CA$505 annual average
Oct
Nov
Dec
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Feb
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Apr
May
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Aug
Sep
Average price per week

Vacation rentals availability Kissimmee

33%for 1 Oct - 8 Oct
54% annual average
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Percentage of available rentals

Vacation rentals in Kissimmee

Rentals in the entertainment hub of the world

Home to Disney World, Kissimmee is one of the most popular vacation 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 vacation rental to choose from in Kissimmee, all offering easy access to the theme parks. If you are looking for a vacation 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 rentals 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 rentals are surprisingly well priced. Many vacation rental offer spectacular golf course and lake views, guaranteeing a vacation that you will always hold close to your heart.

Vacations 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 vacation 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 vacation 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 vacation nirvana in a city where thrill meets chill!

Travellers and activities

Kissimmee for romantic vacations

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 vacations 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: Vacation Rentals and Apartments in Kissimmee

What is the average price for vacation rentals in Kissimmee?

Based on our data, Kissimmee has an average price of CA$415.49 per night, a relatively high one for a city in the USA.

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

If you would like to save as much as possible during your visit to Kissimmee, travel in May (CA$386.06 per night on average), November (CA$386.33), or August (CA$387.24), to find the lowest prices for the whole year.

In which months is it more expensive to rent a vacation rental in Kissimmee?

When booking a vacation rental in Kissimmee, the highest prices are usually found in the month of March (with an average of CA$471.26 per night), followed by February (CA$454.58), and April (CA$452.86).

Are there usually many vacation rentals available in Kissimmee?

It is better to book sooner than later in Kissimmee as only 41% of the accommodations remain available throughout the year, according to our 2020 data.

Which months offer the highest availability?

The most available months are, on average, May (with an availability of 54.4%), September (53.5%), and August (52.6%), according to the trends observed in 2020.

When will it be harder to find an available vacation rental in Kissimmee?

The month with the highest average booked rental figures is February (only 9.2% of properties were available on average in 2020). Followed by March (20.75%), and January (26%).

How many vacation rentals does Holidu have in Kissimmee?

We have grouped together the offers from 13 different providers in Kissimmee, so we can provide you with around 3600 properties. You're going to have a hard time deciding which one to go with!

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

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