The search for the perfect room in Key West began when a good friend from Miami Beach said he wouldn’t mind coming down for a long weekend to visit. He didn’t want to pay too much for a room, he said. Not hundreds upon hundreds. And he’d be happy with whatever I picked out for him. </p><p>But this wasn’t going to be an easy thing finding him a place to stay.</p><p>My friend hasn’t been to Key West in more than 20 years. So I wanted to find a place that would represent the best of the island. And I set out to find something that he could get for $100 — which, I happened to remember, is about what he always paid for a room at the Cosmopolitan Hotel in SoHo in Manhattan when he used to come up to visit me. Why should Key West, I reasoned, be pricier than New York City? It shouldn’t, of course.</p><p>The search took place in earnest last weekend, maybe the single slowest weekend of the year in the Keys. It began with the Lighthouse Court inn on Whitehead Street, across from the Hemingway home and next to the Key West Lighthouse.</p><p>“How much do you want to pay?” the man at the front desk said when I asked how much for a room. I said $100, naturally, and he handed me the keys to a room.</p><p>It was a perfectly nice room, smacky clean and neat, on the second floor overlooking the pool. But it was much too small, with just a few inches on either side of the bed to maneuver around. And the place felt to me a bit more like Nantucket than Key West. Next.</p><p>I walked a couple of blocks to a place I’d passed a week or so before. All I saw that day was just a sign that said “Papa’s Hideaway” hanging off a high fence around a property on Louisa Street, just a block or so west of Whitehead Street. But I knew there was something special back in there. I was right.</p><p>A pretty woman named Andrea came out to the gate to let me in a few minutes after I’d pressed the buzzer. We walked through a lush tropical yard with a small pool over to the left. It felt, immediately, like home — like some place you could really unwind for a couple of days. Or hide out even.</p><p>There are just four rooms at Papa’s Hideaway. The two on the second floor are enormous, with kitchenettes, raftered ceilings and private screened-in porches. It was maybe not exactly the thing for my Miami Beach friend, but an excellent spot nevertheless. I asked the owner if she would let one of the second-story rooms for $100. She said $117 was about the lowest price, but that she’d give it to a local for $100 if she still had a vacancy by noon the next day. She didn’t. All the rooms had been rented for the night. Note taken. Lesson learned. When you take a gamble on a room, you risk losing it.</p><p>The search continued to Duval Street, where I wandered around on the south end, the quiet end. There was a bed & breakfast on the corner near the Southernmost Hotel that had a garden littered with white wicker and tchochkees. The lobby was all teacups and lace. Sort of sloppy Victorian — kitsch without the wink and nod. I veered off, and went in to inquire about places at the wine bar Grand Vin. A blond girl reading a book on the porch recommended the rooms at the Avalon on the 1300 block of Duval — calling them “pristine” and some of the nicest on the island.</p><p>The Avalon is just across the street from the butterfly museum, and there’s a nice coffee/tea shop across the street the other way. It feels really relaxed down here. Sleepy even. I was shown a lovely room furnished with a four-poster queen bed with mosquito netting. The price: $99 for the remainder of the year, excepting Fantasy Fest and a few other big weekends. I would have named the Avalon as the winner and declared mission accomplished except for the grounds. There’s a small pool around back, but it feels dead back there. Like suburbia. Not like an island paradise. I carried on.</p><p>I stopped by La Te Da because, as the saying goes.. “If you haven’t been to La Te Da...you haven’t been to Key West.” The room went for $245, but he’d give it to me for $145. It was nice. But too done. Too much marble and such. I had in mind something more rustic.</p><p>Next was the Heron House, where rooms open onto a lovely pool and are superbly furnished. But they don’t go for anywhere near $100 — unless they’re desperate, I was told. But it wasn’t the sort of place I was looking for anyway. Too couply. And there was no island vibe!</p><p>I lavished praise on the talents of the unnamed men and women who designed rooms at Simonton Court, near the Pelican Poop and Casa Antiqua. There was one I saw that I wouldn’t mind moving into permanently. There was a small black-bottomed pool just around the corner. Enchanting! But well outside that $100 budget.</p><p>I cruised Truman Avenue, passing by a number of places that looked a little too perfect, a little too done. But I did stop at the Truman Hotel where a large sign advertised “affordable rooms.” They were affordable at just $119 for a great room with a glass bowl sink that sits atop the counter. But the grounds are under construction and the rooms feel more city chic than island charming.</p><p>It was just around the corner on Elizabeth Street that I found just what I was looking for: The Blue Parrot Inn. This bed & breakfast is housed in a two-story Victorian home with gingerbread cutout railings and painted wood floors. The Blue Parrot Inn —named, presumably, after the establishment owned by Sidney Greenstreet’s character in “Casablanca” — was built by one of the first mayors of Key West as a home for his daughter. The bedroom on the second floor that looks out on the street usually goes for about $130. But with a steep local’s discount, and on a rainy day in the off-season, it is possible to have it for just $90. Paradise found. Game over.