Kissimmee Holidays 2025/2026

At the heart of this diverse city lies the Old Town, a purpose built attraction depicting a 1950s Florida town. Kissimmee holidays boast an historic downtown area with many restaurants and bars, as well as wonderful Shingle Creek, wetlands that mark the starting point of the world famous Everglades that stretch all the way to Mexico.

A little of it all

Downtown Kissimmee and top cultural sites

The beating heart of Kissimmee is its downtown area, which has 189 historic buildings, interesting artwork to marvel at, and is the location of many popular restaurants and bars.

Monument Avenue is also home to a 15-metre-tall retro piece of art called The Monument of States. A pyramid of colourful concrete slabs, it was commissioned in 1942 as a symbol of peace after the bombing of Pearl Harbour.

Another site to see during your stay is The Colonial Estate – a grand property boasting grand iconic columned porches that’s reminiscent of Gone with the Wind. This house was built c.1916 by J Wade Tucker, a lumber baron from Georgia, and is one of the area’s most famous attractions showcasing a lifestyle that few could afford.

Old Town theme Park and Walt Disney World Resort

At Kissimmee’s heart is the Old Town theme park. Built in the mid 1980s, this family fun destination has been designed to represent a Florida town from the 1950s. Attractions include an outdoor mall with an old-fashioned General Store, the Groovy Store fashion accessories shop and plenty of places to eat. Shoot a pretend gun at Rootin & Tootin’s Shootin’ Alley, or enjoy all the fun and games at the Happy Days Family Fun Centre.

From Kissimmee it’s easy to get to one of the most famous theme parks in the world – Walt Disney World Resort. Explore the Magic Kingdom with countless attractions and rides, Disney characters and entertainment, magical events and tours.

Take a swashbuckling ride in Pirates of the Caribbean land, or fly with Peter Pan on a pirate ship to Never Never Land. Or the nearby Epcot centre is a global adventure that will take you on journeys underwater and to outer space.

A veritable array of places to eat and drink

Kissimmee might surprise you with its varied choice of dining and drinking options. Whether you’re after hearty Italian food, traditional American grills such as burger and chips, or fajitas at a Mexican establishment, you’ll find somewhere to go.

Many restaurants are located in the popular and historic area of Downtown Kissimmee, as are some of the popular bars such as Red Shoe Martini and Breeze, serving cocktails, wines and beers. Their proximity means it’s easy to make a night of it.

You’ll also find plenty of places to eat and drink in the Old Town theme park, such as the aviation themed pub and grill Blue Max Tavern Inc, also a good place to head if you enjoy a bit of karaoke. Plus Old Town is host to the only nightclub in Kissimmee, Sun on the Beach. If you’re planning on taking All Inclusive holidays to Kissimmee, rest assured that the drinking and dining options at the region’s welcoming hotels are a fine match for any venue you’ll find elsewhere.

Explore exotic Shingle Creek Regional Park

Kissimmee sits at the start of the Florida Everglades, which is the largest wetland area in America, and fondly known as ‘America’s Great Outdoors’ by former President Obama. There is a three-kilometre area that can be explored here, but the Everglades as a whole is much larger, flowing all the way to Mexico.

The Shingle Creek Regional Trail is a multi-use area that can be enjoyed by boat, foot or by bike. The best way to explore the wetland, and get a glimpse of the alligators, is to travel by boat, whether on a kayak, canoe or family-sized and escorted airboat.

The diversity of wildlife is beguiling and aside from alligators, there are turtles, and many water birds including coots and herons. There’s a lovely picnic point, and play area for the children in Shingle Creek, too. Cheap holidays to Kissimmee are all about taking advantage of the beautiful natural attractions you can see for free, so plan before you go and make the most of your time away.