Family on outdoor pool chairs

Kissimmee Holidays

Strike the ultimate balance between thrill & chill

Holidays in Kissimmee

Kissimmee is located just south of Orlando and is practically on Disney’s doorstep. There is a huge choice of accommodation ranging from hotels and apartments to deluxe villas with private pools.

With restaurants catering to all tastes and influenced by cultures from around the globe, you could have Mexican quesadillas one day and dine at an Italian bistro the next, while tucking into some all-American home cooking in between.

Imagine an afternoon of theme park action before a relaxing round of golf at one of Kissimmee’s scenic courses. There’s just so much to see and do, you’ll need to stay a little longer to tick everything off you’re your itinerary.

10 Great Reasons to Holiday in Kissimmee

  • Experience the thrills of an Everglades-style airboat ride.
  • Pay a visit to Old Town - be sure to get there early on Friday nights for the all-American Muscle Car Cruise.
  • Sample a vast choice of restaurants from many culinary backgrounds.
  • Take in a show, including the popular Medieval Times Dinner Show.
  • Tee off at a superb array of excellent golf courses.
  • The magic of Disney World is right on your doorstep.
  • Fun Spot America offers sky diving, roller coasters, entertainment and dining.
  • See alligators at Gatorland and zip-line over the swamps.
  • Meet the friendly locals.
  • Shop ‘til you drop! With a range of outlets, flea markets and farmers markets you’ll be sure to find a bargain.

Things to do Whilst on Holiday

Staying in Kissimmee puts you in the heart of the action. Walt Disney World is within easy reach and Universal Studios and SeaWorld are 20 – 25 minutes’ drive. The newly developed Disney Springs is a great place to stroll around during the day and night and is adjacent to Disney itself. Here you can catch a show, enjoy a cocktail, dine out in one of the many restaurants and lose yourself in the world’s largest Disney store.

The fabulous beaches on the East coast (Daytona) and West coast (Clearwater & St. Petes) are just over an hour’s drive from Kissimmee, or for those not hiring a car, day excursions can be booked easily – just ask your Kenwood Travel agent for details. Activities including golf (and mini-golf), bowling, fishing, hiking and movie-going are all readily available. With so much on offer your Kissimmee holiday in Orlando holiday is bound to leave you wanting more.


Here you’ll encounter two distinctive seasons with a hot and wet season from June to September, and a dry season in October to May. Being close to the Tropic of Cancer, Kissimmee will become quite humid, so be prepared!

Interesting Facts About Kissimmee 

  • State – Florida
  • County – Osceola
  • Area – 17.32 sq. miles
  • City population – 59,682

Kissimmee Holidays 2024 / 2025

Book your 2024 & 2025 holidays early in order to take advantage of some of the key deals – call one of our advisors to find out more! For something a little special, we’ll be able to arrange a multi-centre holiday to one of the numerous destinations we have on offer! Let Kenwood Travel reveal some wonderful luxury all inclusive holidays, weddings and honeymoons!

Top Picks

Encore Resort at Reunion

5* out of 5 stars

Superb villa homes in 4 to 13 bedroom categories, with on-site waterpark, luxury amenities and wide-ranging restaurants plus home-delivery catering.

Margaritaville Resort Orlando

4* out of 5 stars

Not many Orlando hotels have a soft-sand beach, waterpark (park admission required) and rustic cottage accommodation. This one does, and that's the just the beginning.

The Grove Resort & Water Park Orlando

4* out of 5 stars

An all-suite lakeshore hotel just three miles from Disney. Tasty dining, four swimming pools and an onsite waterpark await lucky visitors to this Kissimmee retreat.

Windsor Hills 3 Bed Condo

4* out of 5 stars

Offering guests a range of different accommodations, the Windsor Hills Resort is an elegant gated community with a lagoon style pool and whirlpool for guests to relax in.


Useful information

  • Local time GMT (-6)
  • Currency US Dollars
  • Language English
  • Location Orlando
  • Flying time 8 hours & 30 minutes

Destination map