How to Find a Winter Rental in Florida

How to Find a Winter Rental
One of the most common questions I get, especially this time of year, is from people wondering how to go about finding a winter rental in Florida.

Winter rental season here in Florida runs roughly from November through March, but some people extend their stay into the month of April.

The obvious reason for people wanting to spend winter in Florida is to escape the cold temperatures and conditions up North this time of year and to take advantage of Florida’s more forgiving climate.

Its no surprise that once people experience winter in Florida for the first time, they tend to come back year after year.

My family ran a property management company managing several winter rentals for nearly 30 years, and we had many repeat winter tenants. I’d estimate that in any given year, at least 75% of our clients were repeat renters. Some rented the same exact unit consistently for more than 10 years straight!

So be careful, once you try it, you’ll likely be hooked.

John D. Rockefeller

History of “Wintering” in Florida

The most widely documented accounts of people wintering in Florida date back to the era when the country’s elite like John D. Rockefeller, Henry Ford, Thomas Edison, and others with the substantial means required at the time would make the yearly journey by rail south for the winter.

In fact, John D. Rockefeller’s goal was to live to be 100 years old, and though he fell about 2 years short of that goal (he died at his home here in Florida at the age of 97), he thought that traveling with the seasons would help prolong his life, and it likely did.

If you’re interested in learning more about this piece of Florida history, you can visit the winter homes of Thomas Edison and Henry Ford in Fort Myers, Henry Flagler’s Whitehall Estate in Palm Beach, or the winter home of John D. Rockefeller at The Casements in Ormond Beach.

Getting Started (And a Word of Caution)

These days most people start looking for a winter rental online.

While this is a good idea, and we’ll share some places to start your online search below, you need to be extremely cautious when responding to advertisements placed on websites advertising rentals.

There have been reports of many rentals scams in the last few years, and people have come up with some pretty creative ways to (illegally) separate you from your hard earned money. Learn more about some of the popular rental scams and how to avoid them here.

"Snow" on my neighbor's pool enclosure here in Florida. Winter 2010. Brrr.

“Snow” on my neighbor’s pool enclosure here in Florida. Winter 2010. Brrr.

Property Management Companies

Your first stop on the road to finding a winter rental should be to search for property management companies in the area you wish to winter in.

This is a fairly simple task, just fire up your favorite search engine and type in some variation of:

“CITY NAME property management” or “CITY NAME winter rentals”

This will typically return several good results for you to check out and explore. I recommend going the professionally managed rental route for a couple reasons.

One reason is that you’ll have a convenient point of contact should anything go wrong during your stay. Stuff happens…refrigerators go out, heaters go on the fritz, etc…and assuming you’re renting through a quality property management company, your problems will be short lived.

A good management company just makes the whole rental experience easier from end to end. When my family managed rentals, we would have a welcome basket of expensive chocolates and gourmet foods waiting along with a folder full of useful information that tenants might need during their stay.

Plus, by going through a property management company you are much less susceptible to rental scams like I mentioned earlier in the article. My advice is to exhaust all efforts going the property management route before moving on to the others.

If the property management route does not work, you should then try the private owner route. For this, you’ll need to check out a couple of sites, as unfortunately there’s not really just one dominant rental listing website.

“By Owner” Winter Rental Listings

Here are a few places to check where private homeowners typically list their properties for rent.

In most cases you’re going to have to go through the list of available rentals and figure out which properties might be available for the winter months you wish to rent for.

VRBO and HomeAway – These are two of the most popular rental listing websites and where you will find the bulk of the listings available.

Again, you are going to have to do quite a bit of leg work looking through each listing that might be relevant to you, and ultimately contacting the owner directly to negotiate rental rates and terms.

Dwellable – This site also deserves a mention as they “round up” a lot of the rental listings available on other websites and present them in a much more visually appealing format. They also have a great iPad app if that’s your sort of thing.

At the sites listed above in many cases you’ll find “nightly” or “weekly” rates listed, so you’ll need to make contact with the owner of the listing and let them know your desired length of stay and negotiate from there.

Just know that it’s not uncommon for winter rentals to carry a 25-50% premium vs. your run-of-the-mill long term rental.

Come On Down

If you made it this far, you are armed with the knowledge you need to successfully find a winter rental in Florida.

Come the peak of the season, you certainly won’t be freezing your behind off or shoveling snow, and you might even be out playing golf or enjoying a nice walk on the beach.

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