
See also:
25 Best Places to Retire in Florida
Ultimate List of 55+ Communities in Florida
If one of your concerns is that you move to Florida for retirement and your kids and grandkids never come to visit, that won't be the case if you end up in Kissimmee.
In fact, you might have a hard time getting them to leave!
Kissimmee is located just south of Orlando and is just minutes from popular attractions like the Walt Disney World Resort, Universal Studios, Sea World, and more.
They call Kissimmee the “attraction zone” and it's easy to see why.
Where to Retire in Kissimmee

Solivita is an award-winning retirement community in Central Florida’s attraction zone. No matter where you live within this lush gated 55-plus community in Kissimmee, you can easily walk, bike or drive your golf cart to indoor and outdoor dining venues, state-of-the-art spa and fitness complexes, pickleball or tennis courts, and other facilities for sports and games.
With two stunning championship golf courses, intimate neighborhood centers, softball field, miles of green space for walking and biking, and too many classes and clubs to count, you will have many ways to enjoy the Solivita life.
Home prices start in the $200k's.
Four Seasons at Orlando – Kissimmee, FL

Four Seasons at Orlando is a gated community of 557 single-family homes located in Kissimmee, Florida, just south of Orlando. Amenities here include a 14,000-square-foot clubhouse with a state-of-the-art fitness center and an arts and crafts room, as well as an outdoor swimming pool, pickleball courts, and access to the 18-hole Mystic Dunes Golf Club.
There are 7 floorplans that range in size from 1,428 to 2,328 square feet. Prices start in the $300k’s.
Tohoqua Reserve – Kissimmee
Tohoqua Reserve is a 55+ Active Adult neighborhood from Pulte Homes. It is located within a master-planned community in Kissimmee. Tohoqua Reserve is less than 10 minutes from the Florida Turnpike, making commutes to all major areas of Orlando much easier.
Amenities include a private amenity center exclusively reserved for active adults with a clubhouse, resort-style pool, sports courts, and more.
Single-family homes and villas are available in sizes ranging from 1,500 sq. ft. to more than 2,800 sq. ft. Prices start in the $300k’s.
Here are some homes currently listed for sale in 55+ communities around Kissimmee:
Where to Stay
You've got plenty of options when coming to town to visit and tour communities, but one place stands out, at least for me, and that's Gaylord Palms. It's part of the Marriott family, and 9 times out of 10 it's where I stay with my family when we visit the area.
Staying at the Gaylord is like getting a mini-tour of Florida, as the resort is divided into different themed areas that represent different parts of Florida like the Everglades, St. Augustine, and Key West. You really have to see it to believe it.
Also, every year at Christmastime they have an event called ICE, where you get to walk through a 9-degree indoor winter wonderland complete with ice carvings, ice slides, and more. This event is popular with people from communities like The Villages and others, and they come in by the busload just for this event.
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Theme Parks

Kissimmee is literally just minutes from the front door of the Walt Disney World Resort and its various parks like Walt Disney World, Epcot, Animal Kingdom, and Hollywood Studios.
About a 15-minute drive away are two more parks in Universal Studious and Islands of Adventure, and right down the road from there you also have Sea World.
Like I said before, with easy access to all of these parks, your guests may never want to leave.
But don't just think these parks are only for the young ones. Some of the best times I've had have been while visiting them with just my wife and I.
One of our favorite events is the Epcot Food and Wine festival held over several weeks each Fall. If you enjoy good food, exploring new wines and beers, this is a can't miss event.

Planning to Work in Retirement?
Lots of people, even if they didn't initially plan to, end up getting part-time work in retirement.
Sometimes this is to make a little extra money to pay for trips they want to take or to cover some bills, and other times it's just to stay active and keep a routine going.
But whatever the reason, the theme parks are a great place for retirees to consider working, and they employ thousands of retirees as part-time employees already.
In addition to the pay, they offer some great perks like free park admission and other discounts that can come in handy when friends and relatives do visit.
Wife is not over 55 even though I am. Is that a problem?