Retirement Living in the Florida Keys

Sunset in Key Largo

There are some places that are nice to visit, but you wouldn’t want to live there.

The Florida Keys is perfect whether visiting for a weekend or deciding to make it a permanent home.

An idyllic tropical setting at the tip of the United States combined with a myriad of recreation, entertainment, and cultural opportunities create the ideal place to spend the next stage in life.

Whether retiring or looking for a change of scenery, check out your options in the Florida Keys.


The steady climate of the Florida Keys is a secret known to residents. The temperatures in the winter rarely get below the 60s. Summer heat is not a problem because the ocean helps to keep the temperatures of the cities in the Keys in the 80s.

Most people are surprised to hear this, as it does not sound like the weather in other parts of Florida at all. Where I live, in Daytona Beach Shores, we regularly get up into the mid to high 90’s in the summer, and there are times when we experience the teens and twenties during the winter. Granted, some people like to experience the different seasons, but if you prefer steady ideal weather all year ’round, the Keys might be for you.

Into every life some rain must fall, but the rain usually waits until the summer to fall in the Keys. When the rain does fall, it usually takes the form of short-lived thunderstorms in the afternoons. Few days are complete wash-outs from hours of rain falling. The winter months are the driest months, only experiencing brief rains, if any.

Some people are concerned about hurricanes when considering a move to the Florida Keys, but these are not as much of a problem as outsiders think. Hurricanes do not hit the Keys every year, and when they do, it will likely be in the late summer months.

Preparation is the key to avoiding serious damage to property, and with hurricanes, time to prepare is given. Weather forecasters usually provide ample time before a storm hits to prepare a home and evacuate, if needed. This means that Keys residents are never caught off guard. The local building codes are such so that most newer homes will ride out many of the tropical systems that pass through the Keys.

The one downside during hurricane season though is that whenever a big hurricane threatens the Keys, residents and visitors are urged to evacuate. Sounds simple enough, but it can get a little hectic with one road in, and one road out of the Keys (U.S. 1).

Southernmost Point Buoy

Getting There

You can certainly get to the Keys by boat. In fact, before the 1910’s and the completion of Henry Flagler’s Overseas Railway, boats were the only way to get to the Keys.

As I mentioned previously, U.S. 1 is the only road in and out of the Keys. The Keys begin about 15 miles south of Miami. From that point it’s about 3.5 hours to drive all the way to the bottom of the Keys in Key West.

You can also get to the Keys by plane. Both commercial and private planes use either Key West International Airport, or the Florida Keys Marathon Airport.

Arts and Culture

Though it rests at the tip of Florida, the Keys maintains its own identity when it comes to the arts. Museums abound in the Keys, focusing on such diverse topics as the history of diving, Ernest Hemingway and shipwrecks.

Even if it is possible to visit all of the museums the Keys has to offer, there are still performances to attend. The TIB Bank amphitheater offers an outdoor venue for musical performances on Plantation Key. Concerts are offered through the Florida Keys Concert Association and the Upper Keys Concert Series and Islamorada Community Entertainment.

Several live theater groups make the Florida Keys their home. The Keys Players, the Waterfront Playhouse, the Red Barn Theatre, and the Tennessee Williams Theatre are just a few of the options for catching a live performance. These groups provide a wide range of genres in their performances, ensuring that there will be something to suit the tastes of every theatergoer.


The Florida Keys are full of history. Historic sites around the Keys convey this to visitors. Many residents neglect to spot these gems in the rough, but for anyone newly transplanted to the Keys a trip to the historic sites will give a full picture of the area.

Harry Truman has his presidential library on Key West, called the “Little White House.” It is Florida’s only presidential library. Fans of Ernest Hemingway will want to make a stop at his home in Key West. Other museums focusing on the history and culture of the Florida Keys should be regular destinations for any resident with an interest in history.


Outdoors types will have nearly limitless recreation options. Beaches abound in the Keys where fishing, swimming, snorkeling, and diving can be enjoyed. Nature preserves and parks provide a quiet getaway for hiking or birdwatching. Indian Key state park, Fort Zachary Taylor state park, San Pedro underwater archaeological preserve state park, the Lignumvitae Key Botanical State Park, and the Crane Point nature center are available for recreation for residents and visitors alike.

For golfers, a large number of course, both public and members-only, are scattered over the Keys, and the climate of the Keys will ensure that every day is a great day for golf.

Spas offer a different way to unwind from the stresses of life. A weekly treat of a visit to one of the many spas in the Keys should be in order, especially for retirees who want to make the most of this new stage of life.

Real Estate

While most people visit this website in search of Florida retirement communities, you won’t find many (if any?) dedicated retirement communities in the Florida Keys like you see in other parts of the state. But, there are some great communities, nonetheless.

The first step would be to take a trip to the Keys, possibly working your way down the line over the course of a week or two and spending time in different places. There are plenty of hotels throughout the Keys, and for every budget. But you also might want to consider a vacation rental owned by a private homeowner. You can find these on sites like, just know that rates will vary depending on the time of year.

As you are visiting certain areas, be sure to pick up any real estate magazines you see in grocery stores or hotels, as these will give you a good idea of what’s available in that particular area.

A quick Google searches yielded the following Florida Keys related real estate websites:

…and many others. You should certainly do your own search as well.

Follow the other tips I spell out in my book Florida for Boomers such as checking out national real estate websites like,, and

In the end, moving to the Florida Keys requires prior planning and thought put into the decision, but once people move to the Keys, they often wonder why they did not do it sooner.

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