The Key West Mystique

Key West Island News


Key West Island News connects Key West residents and friends of the island, fosters our One Human Family culture and advances understanding of shared goals for our island community

What Key West season

Been down on Key West’s Duval Street? You might be wishing for cruise ships

By Linda Grist Cunningham, editor and proprietor

Linda Grist Cunningham is editor and proprietor of Key West Island News and KeyWestWatch Media LLC. She and her husband, a park ranger at Fort Zach, live in Key West with their Cat 5s.


I hollered last weekend at two cyclists who were blithely pedaling the wrong way on Fleming near the intersection with Duval. They came ripping out of the entrance to what is one of Key West’s loveliest (and likely expensive) vacation rental houses, turned left without looking, almost head-on into a car and, well, I was annoyed.

“One-way street,” I yelled. The guy about wrecked his bike trying to figure out both where I was and what he was doing. The woman behind him? She waved and called out happily, “Oh, we know. It’s OK. We’re locals.”

When I said, “that’s a rental house,” she grinned and yelled back: “Well, I think that counts.” And off she pumped, turning right on Duval. I sighed.

Mary, Joseph and the Wee Donkey, we got what we wished for in all that re-imagining we did last year during the Covid shutdown: Instead of cruise ship passengers, we’ve got wealthy visitors who fly in, book multiple nights, spend money and redefine local to include the receipts for a rental bike and a vacation house.

This is what we have come to. Vacation renters who love laying claim to being locals spending thousands of dollars (often tens thereof) a month for one of our houses. Hotel rooms and transient rentals going to upwards of $1,400 nightly with the cheapest in the triple hundreds — plus resort fees. You want a month in January? Nothing too fancy? Expect $10,000 and way up. I found one for $60,000. This is, to be sure, assuming you find one available. There’s slim pickings out there — even in hurricane months — through the end of the 2022 season.

Key West is packed. The skies are filled with commercial and private jets. There are so many illegal scooters, electric bikes and golf carts on the North Roosevelt promenade that we ought to give the thing a street name, charge a toll and call it an express lane.

The island at the start of hurricane season feels more like high season than what has usually been the start of the quieter summer. Long lines, scarce reservations, no parking and a real estate market so hot that houses are being snapped up, sight unseen on a cash offer. Friendly acquaintances say they’ve been told by their agents to make sure they have a backup plan for where to live because houses are selling and closing so swiftly that one might find oneself scrounging for a place.

Key West is doing what Key West has historically done so well: Take advantage of anyone willing to pay the price — any price — for a bit of island pixie dust. The revenue is rolling in and the people who set prices are pushing the limits in search of that point at which they can go no higher. From what we’re seeing with room, food and rentals, it’s probably safe to say they haven’t seen the top.

We need to get it while the getting’s good. Because there’s every reason to believe that once the rest of the world re-opens after Covid, Key West’s record-setting visitors may decamp for places cheaper with way better beaches. We won’t know until deep into 2022 whether today’s crowds and revenue are a Covid-induced fever.

Look, I’m thrilled for local businesses and employees who benefit in boom times. They suffered unimaginably in 2020; it’s a good thing to refill coffers and savings accounts. I am delighted at the improvements in water quality with now a year-plus of no cruise ships churning things up. I am thrilled that tourist tax revenue that supports the county and state efforts to preserve environmentally sensitive land has returned to pre-Covid levels and likely to go even higher. There are plenty of reasons for being giddy.

But, let me just lay this out: We ought be careful what we wish for. So far what we have wished for has brought us a packed island in June; so many planes that we live in a constant glide path from 6 a.m. to midnight. Your friends and family (well, mine anyway) can’t come to visit because they can’t find a place to stay, much less afford it. Houses that sell are unlikely to be a family’s forever home; instead Old Town and its neighbors are becoming one gigantic vacation rental playground.

Mark my words, the day will come when we miss the days when 50 percent of our visitors heard a whistle at 3 p.m., and like ducklings returning to mama, they climbed aboard their cruise ships and sailed away. Leaving the locals in peace.


  1. Charles Layno

    My dream of living in the Keys is drifting farther and farther away. Due to sky high prices, we decided to forgo a visit this fall and hope for better prices in Fall 2022.

    • Linda Grist Cunningham

      Oh, Charles, I do understand and yet I encourage you not to give up hope. I do think we’ll see a return to less jaw-dropping prices next year. I don’t think anyone in Key West today believes these levels of visitors and money are sustainable.

      • Charles Layno

        I sincerely hope not. We are talking about maybe seeing about doing a one year rental and see what we can get in jobs and if we can pay the bills, sell everything here and just rent. It might be cheaper in the long run not having to pay the insurance and taxes. Did a quick envelop pass on the numbers the other day and renting is a little cheaper than outright owning. It surprised me. Will have to sharpen the pencil and really see if the numbers scale up. If so, that might be the ticket to paradise.

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