Key West? Yes! Miami? Yes! Cudjoe Key? Never heard of it!

When we first started looking to buy our vacation rental property in the Florida Keys, I sought the advice of family and friends.  Even strangers.

I’m a great believer in seeking multiple opinions.  “If two people agree all the time, one of them is unnecessary.”  I like to hear competing and conflicting opinions.  Then I’ll make an informed, and hopefully great, decision.

After quickly ruling out the Northeast and Central States as a desirable year-round vacation destination, we flew down to Miami’s South Beach and started driving down the coast on the Overseas Highway towards Key West.

We agreed on what we were looking for:  Price and location were not as important as the “Wow!”.  It also had to be a good investment.  It doesn’t make any sense to buy a vacation rental with great “Wow!” which will end up in foreclosure.  

We were almost at the end of our journey, and it looked like we would be coming up empty handed.  The end of the road was literally just a few miles away.  Then we stopped at these vacation rental cottages on Cudjoe Key.  From the dock we looked out at the ocean and the offshore islands, and we both said “Wow!”  Then we walked through the main house and looked around, and again said “Wow!”  Then we walked into one of the conch cottages.  They were built in the 1920’s and had survived the continuous battering of a heartless ocean.  But the previous owners had started a loving renovation.  And we found character in the cottages that had been missing from the motels and hotels we were staying in and other properties we looked at.  The cottages had earned the right to live on. 

These cottages had survived the the Great Depression, the Great Hurricane of 1935 that wiped out most of the Florida Keys and the Flagler Railroad, and the other hurricanes that pummeled Cudjoe Key and Key West and the other islands in the Lower Florida Keys through the latter half of the 20th century.  These “conch cottages” had a quality and spirit that was missing from all the vacation homes we had seen.  Most houses in the Florida Keys were built during the last 50 years with a flimsy almost cardboard feel.  They are cheaply built and easily replaced when they wash away.   The “conch cottages” on Cudjoe Key were built before these pre-fabricated stilt homes took over the landscape.  You some how know they will be here years after we are gone.  

Miraculously nature had spared these little houses, as storm surge after surge washed all of their neighbors away.  The cottages could never be built today – but as long as nature left them standing – no one would take them away.  And the vacation homes are properly zoned to allow vacation rentals.

“Gosh,” I thought, “Hemingway passed by these cottages on his way to Key West.  Maybe he visited friends who were staying here.  Maybe he seven slept here,”  I though with a smile.  I thought I could almost hear the long gone Overseas Railroad blowing its whistle in the distance. 

“Wow!  This is it!”  my wife said.  Now we just have to work out the finances.  The Realtor overheard us, and smiled.  I think she started dreaming of sitting behind the wheel of that sporty red car back on the dealer’s lot.  She could smell the commission money in her hand.  A couple months and it looked like that car would be sitting in her driveway.

But soon we were back in New York, surrounded by family, mentors and confidants, most of them trying to talk us out of buying the vacation rental property.  One of them, Howard, said “What?  Where?  Cudjoe Key?  Never heard of it!  Key West?  Yes!  Miami?  Yes!  Cudjoe Key?  Never heard of it!  Who is going to want to vacation on Cudjoe Key?  Why would anyone vacation on Cudjoe Key?”

We talked it over.  The money was a lot.  I tried in futility to explain.  And we seemed to be at the top of the Real Estate market market – no where to go but down.  It didn’t make sense economically.  It was not a great financial investment.  No one, except maybe Uncle Vinny, thought it was a good idea.  This was becoming an emotional decision, not a financial one.  It was a heroic decision, not a sensible one.

We talked some more.  “Remember, it has the ‘Wow!'” my wife reminded me.

So against the advice of Howard, one of the most savvy (and richest) real estate investors we knew, we bought the vacation rental property on a tiny, almost unknown island in the Florida Keys: Cudjoe Key.  We packed up the family and drove south as far as we possibly could. 

And this started a strange and wonderful adventure we could have never planned – nothing like anything we could have imagined…


Cudjoe Key Sunrise, originally uploaded by Key West Baseball.


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