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

Key West neighborhoods

Key West neighborhoods | Which one’s the best? It depends

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.


Last week a neighbor and I kinda smugly patted ourselves on the back for decisions we made in wayback times to forego a house in Old Town and instead move to The Meadows. His wayback is four decades, give or take a decade, ahead of mine, but we chose The Meadows for the same reason: We wanted to be away from the busy world of Old Town — and that was before Old Town became tourist central.

The Meadows back then was a respite from all that bustling. It still is, but we see the cracks in our Key West neighborhoods. Fewer homes are owner-occupied year-round. My friend and I can look down our blocks and see empty houses. Some are vacation rentals; more are second homes for snowbirds or investors. No one except the pool guys and the landscapers show up for months on end.

Where once my block was all full-time residents, it’s less than half. In season, the traffic picks up, the voices in the street have been over-served and the arguments over where to go next are laced with, well, bad words. I get it; they’re on vacation. They’re escaping from those nasty mainland winters. But it’s weird to live in a neighborhood where such transience is becoming the norm.

Just after Covid masks disappeared, while sitting in a local doc’s waiting room, one woman said to another, loudly enough for me to overhear: “Haven’t seen you in a while. How are you doing,” said one. “Oh,” said the other, “OK I guess. Sitting on my porch watching rich people walk up and down thinking they own my neighborhood. Unfortunately, some of them do.”

They glanced at me, uncertain perhaps how I would react. I nodded, added a thumbs up, mouthed “same” and returned to my book. They nodded back.

That simple exchange is haunting.

Key West neighborhoods
The quietest neighborhood is the Key West Cemetery in Old Town. Photo by Martha Hubbard.

The transition of Key West neighborhoods

The transition to a tourist destination, which started in Old Town, is spreading with the momentum to change forever the unique characteristics of Key West’s historic neighborhoods. Old Town is close to unliveable unless one adapts to endless noise, roaming crowds, drunks using your car for a bio-break and music so loud and so late. Old Town has become endless party, fun at times for everyone, but not so hospitable as a place to live.

An Old Town address gives one a bit of additional status. It is, or was, the Key West of gracious wooden houses, cigarmaker cottages, sandy walking lanes, sea captains and a good gossip over the fence with a neighbor. I suspect for many their personal Key West Mystique remains firmly rooted in Old Town.

So if all that be true, why were my friend and I congratulating ourselves for choosing The Meadows over Old Town? When we made those choices, The Meadows was a younger suburban sister of Old Town. Similar architecture, but with more concrete blocks. Wider streets but fewer lanes. More parking, off street and on. A family neighborhood for working folks and far away from the tourists downtown. It’s still mostly that but not for long.

Key West Island News
One of many maps that show Key West neighborhoods. This one doesn’t indicate Bahama Village but instead includes it as part of Old Town South-of-Truman and Old Town North-of-Truman. That’s New Town in green to the right and includes the airport.

There are seven-ish neighborhoods in Key West: Old Town, The Meadows, Casa Marina District, Bahama Village, New Town, part of Midtown and Truman Annex. Some slice those up even more to get a marketing boost. You’ve got Mid Town (East and West). Old Town North-of-Truman and Old Town South-of-Truman. There’s Uptown and Downtown and the White Street Gallery District. Sunset Key and the Golf Course, though I’d argue neither of those should count as Key West since one is on Stock Island past the Cow Key Bridge and the other’s, well, a U.S. Navy-made fill dump offshore, albeit with expensive real estate.

Now, if one doesn’t live here, it’s tough to grasp why on an island this small it even matters where you live. After all, from the westernmost point at Fort Zachary Taylor State Park to the Cow Key (now Cheryl Cates Memorial) Bridge the island’s four 4 miles wide. From my house in The Meadows to the White Street (now Edward B. Knight) Pier, it’s a mile. It’s a meandering 1.5 miles in the other direction to the Key West Museum of Art & History at the Custom House.

We live cheek-by-jowl and quickly learn to ignore the squabbles of the neighbors, slammed doors and flushing toilets. We live where “which end” is not an uncommon question when talking about some of the longest streets on the island, like Olivia, Duval, Whitehead, Simonton, Southard and Eaton.

The 25,597 of us who live here know what makes our neighborhood ours, so to speak. And like the two women chatting in the doctor’s office, it’s darn hard not to lament the loss of what used to be.


  1. Pam G

    We lived in mid-town (near the salt ponds) for years and loved it because we felt like we lived in “the country”. Duval Street was very far away, both culturally and noisily. It was quiet and peaceful at the end of our lane. Twenty three years ago we moved to Bay Point MM15 – I know, not Key West proper but still with a Key West, 33040 address. We really felt like we lived in “the country” on Bay Point – because 23 years ago it was THE Country. Now a-days, Bay Point often feels like downtown Key West. The traffic is significantly heavier through the neighborhood, most of the old timers are gone. Lots of new construction. Many homes either occupied by lots of roommates (3 couples in a 3 bedroom house = 6 people and 6 cars) due to cost, or VRBO and AirBNB, or mostly absent second home owners and/or snowbirds. Everything changes, as do each of our neighborhoods. Key West is a special place. We are moving way “Up the country” to North Central Florida. Big spaces, rolling hills, rivers, lakes, springs, trees and forests. Lot’s of former Key Wester’s is the vicinity. We’ll always treasure our Key West neighborhood memories, but we’re working on a whole new set of neighborhood memories.

  2. Douglas Chase

    “Darn hard” … so demure. Great article.

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