Why Key West? Rentals We Have Loved and Lost, and Other KW How-Tos

We used to find a Key West rental the easy way. Click around on VRBO dreaming for a while, pick the perfect place, contact the owner, send a small deposit. Done.

Uh, no. Not any more. We’ve watched the rental market change dramatically since 2006, and now it’s more like 1) stalk renters who rave about a place, then follow them home to snag the address (we’ve done that); 2) sell all our worldly goods to pay enormous deposits a year in advance (may do that soon); or 3) bake cookies for the neighbors so they’ll invite you back (I always do that. Just ask the neighbors).

People often ask us how we find rentals here, year after year, and also why we winter in Key West instead of Arizona or Hawaii – where practical Seattleites go. We make this irrational choice for one reason, in fact – the same reason we still use Facebook even though people rant there sometimes. But first, some background.

Key West is impractical, true. Hurricanes threaten frequently (make sure to purchase your travel insurance before the storm is named or you are out of luck). It’s expensive, difficult to reach (for us), and parking is absolutely impossible. Last year someone put a huge scrape down the side of our rental car, weaving home after some drunken fun, perhaps? We’ll never know since the scoundrel didn’t leave a note. 

We walk everywhere, but sometimes it’s like playing Frogger for real, dodging cars and wobbly bicycles manned by gaping tourists. And you should see how monthly renters clog the grocery aisles on the first of every month. Locals are very helpful  – (no, you don’t need a can of RAID because the exterminators come once a week to spray!!) – but they must have little parties when we’re gone to celebrate all the new-found parking spots. 

Key West may not be good for our pocketbooks or rental cars, but this impractical town won our hearts years ago. And just like love, it’s hard to explain – how it happened goes all the way back to a scary Key Largo storm, a few chickens, a drink or two, and good friends who told us “We have to talk.”

Back in 2006, all we knew was a guy named Allen and his wife Gail, who said, “You need to come down to Key West.” Ok! So we cruised down U.S. 1 into the Keys amid lots of sunshine and balmy breezes,  Margaritaville playing on the radio. When we reached our boutique beachfront lodgings, Padre sent a snarky ‘We’re in Paradise’ photo to his co-workers.

He regretted this move later that night when temperatures plummeted and howling winds shook the roof. I kid you not: This was as we watched the 1940s classic noir hurricane film, Key Largo, shivering under blankets. Welcome to Paradise, we joked the next day when we observed locals in heavy overcoats at the grocery store, grimly shaking their heads.

Turns out we arrived just before one of the coldest days on record. So we weren’t impressed with Florida at first even though the weather soon climbed back into the 70’s, as it usually does after a chilly day or two. 

‘Chilly’ of course is a relative term. We shed our REI down jackets and order iced Starbucks when Seattle reaches the 50’s in winter. Usually it’s in the 30s and 40s, with an occasional snowstorm to remind us where we live, which is not far from the northwestern-most point of the contiguous United States. That actual point is Cape Flattery, a couple hours up the road – windswept bluffs, fierce storms, deadly shipwrecks, and relentless sheets of cold rain. Our home is a milder form of that in winter, minus the shipwrecks.

The sleet-filled winters didn’t used to bother me, since I love to make soup and sit by a crackling fire with a good book on my lap. The last few years, though – that sleet seems to slice right into my bones when I slip outside to get the morning paper. I made the mistake of googling “why do older people get so cold?” to learn the shocking truth. (I’m not going to tell you. If you’re over 50, google it if you dare.)

So we come to the southern-most point, Key West, to escape the cold, but it’s more than that. Take the colors, for instance. Remember that scene in the Wizard of Oz when it switches from black-and-white to full-on Technicolor? That’s how it felt to open the gate of our friends’ charming historical cottage, painted bicycles perched against the fence, into a lush tropical garden centered around a sparkling plunge pool. Inside, bright light streamed through the windows, illuminating the Caribbean colors everywhere. Key West still feels like that – life in full color – and the rentals we have been fortunate enough to occupy over the years have all had a similar vibe. 

In our first few years here, we did the Duval Crawl, the Conch Train, the Sunset Celebration, Sloppy Joe’s, the Shipwreck Museum, the Hemingway House – all the must-do tourist stuff, but we spent more time in the Upper and Middle Keys. We mistakenly thought it was the Keys – not Key West – that drew us back, year after year. But over time, Key West hooked us as we came to appreciate the rest of its charms. Thanks to our friends and the wonderful people we met through them, we learned that in Key West:

• There’s a vibrant theatre scene happening here in the winter. This year, we’ve seen a Broadway traveling show at the Tennessee Williams Theatre, a side-splitting holiday comedy at the Red Barn, and an Ibsen takeoff at the Waterfront Playhouse. Some years we take in a drag show, and Key West has some of the best drag shows anywhere. And on a rainy day, we can always catch a movie at the Tropic.

• We can choose from a rotating cast of live music bands every day and night of the week, or catch a classical music concert, as I did a couple weeks ago when I heard noted organist Chaz Bowers play the refurbished St. Paul’s organ down on Duval Street (today I get to see a violinist). Last year we joined Arlo Guthrie as he sang Alice’s Restaurant, and caught the Honey Island Swamp Band, my fave New Orleans Band, at the Green Parrot for free. Turns out lots of class acts love to perform in Key West during the winter (I wonder why?). 

• While there are only two bookstores in town, everyone seems to love to talk books here. I am an honorary visiting member of a local book group, and my Key West friends frequently discuss and recommend the books they’re reading. I haven’t attended the Key West Literary Seminar, an annual winter gathering of readers that brings in noted authors over a long weekend, but hope to do so one of these days. 

• In the past I’ve joined a gym, and swum laps at the local college. This year I’m trying yoga classes. No one cares that I’m bad at yoga or last touched my toes in 1985. Everyone’s supportive, no matter my age, gender, affiliations, or questionable fashion choices. This is Key West, after all.

• Every weekend there’s another festival or market to check out. Last weekend it was the Key West Seafood Festival and the Key West Artisan Market, this weekend it’s the Food and Wine Festival and the 34^thAnnual Key West Craft Show. We’ve spent pleasant hours wandering through numerous art galleries downtown, and just may have to acquire another tropical artwork for the Northwest beach house before we leave.

But lots of cities have all that, don’t they? Sure they do, and Seattle is no slouch in the “things to do” department. But I can’t ride my bike to the Seattle Rep (well I could, I suppose, but I’d die at the end), and a trip into the city is an all-day affair, involving tolls and ferries. Here in Key West, we just walk or hitch a ride, and now there’s Uber and the Duval Loop Bus if we need them. Walks home amid Key West’s twinkling lights can be magical, and sometimes we plunge into the sparkling pool for a late-night dip. (Try that in Seattle in January.) 

And we love Key West’s quirkiness, the open, all-are-welcome ethos, represented by free-roaming chickens, as well as the ‘One Human Family’ bumper stickers proclaiming the town’s motto. It can be a bit disconcerting when the chickens join us for dinner, of course, but it’s all part of the fun.

When we decided to spend most of our Florida time in Key West, our good friends took us out to have ‘the talk’ over a couple drinks. They explained the facts of Key West life to us, main point being: It’s time for you to get serious and rent a place for a month. It’s cheaper (it was back then, but now not so much), and you obviously belong here, don’t you? 

We did belong here; they were absolutely right. So we reserved our first month-long rental seven years ago, thinking (foolishly) that we’d rent the same place, year after year, as so many other people did. 

But we were wrong about that ‘year after year’ part. Turns out, most Key West rental owners have a ‘right to first refusal’ policy, so current renters get first dibs on the next year. Great if you’re the current renter, and this worked in our favor for a few years. Then the owner of our first rental raised prices to Must-Win-Lotto rates, in part because Key West’s popularity keeps pushing up rental and real estate rates in tandem.

We lucked into our second rental around the corner from our first, and thought we were saved. But no: When our new owner sold the place, we learned that the rentals we found online were already spoken for due to ‘right of first refusal’ policies. To become favored yearly renters again, we needed to be very lucky or very rich. Maybe both.

We got lucky one more time, and snagged a place that someone was giving up. We’ve been in our current place two years, and now it’s about to become a year-long rental. 

And by the way, we’re actually glad our current rental is going to join the ‘local’ rental market. Wealthier investors have priced little guys out of town, just as they have in many popular U.S. cities, making affordable housing for year-round residents impossible to find. In 2017, Mother Nature added insult to injury when Hurricane Irma destroyed plenty of cheaper real estate up the road in Big Pine Key and farther north. The average teacher’s salary here is $55,000, and the cost to rent a small two-bedroom apartment averages close to $2500 a month. Back in my teaching days I could not have afforded to live in Key West, that’s for sure, and I’m sure today’s teachers struggle to do so as well.

Poverty is no stranger to Key West, either. Despite its many wealthy residents, the balmy winter weather attracts a growing homeless population. Key West also includes many senior citizens, who cling to their modest homes despite the tax increases. Padre has been a helper this year with Metropolitan Community Church’s Cooking With Love  program, which last year alone served close to 11,000 meals.

So the place has its problems, one of which is snowbirds like us, pushing up prices. We get that. Yet we keep coming back, and it’s not because of Key West’s ambiance, the cultural opportunities, or even the weather, although all those factors are part of the draw. The most important reason we keep coming back? We’ve made friends here, and Key West feels like home. 

I mean think about it: why doesn’t everyone quit Facebook, since people act badly there, get all political, offend each other, and post embarrassing things?  I don’t know about you, but I stay on Facebook because so many of my friends and family are there, and I get to share a bit of their lives, even if it’s only a snippet. 

We treasure our Key West friends who have helped make this place feel like home, just as we love our far-flung friends and relatives scattered hither and yon around the globe. That’s because the way we look at it, there’s nothing more valuable in life than our connections with folks who choose to share the road of life with us, if only for about six weeks each year.

So Key West is stuck with these two Seattle snowbirds at least for the near future, and one of these days when we slow down on world trekking we’ll stay a few months, we hope. And good news! We’re set for next year. We changed our month to December (lower rents then) and found a charming historical cottage on Poorhouse Lane. 

Quite the appropriate street name, don’t you think? Key West might make paupers out of us yet, but until then, we hope for a few more winters here in Paradise with the chickens – and with our Florida friends.