Westwinds Inn

We had a great week here, and it was surprisingly quiet for Key West. The location made it easy to walk around town, and our room was always in perfect shape when we got back. The cleaning staff were friendly and did a great job. It rained one day, but they had umbrellas guests could borrow. The coin laundry was handy for packing light, though we had to go out for soap because we didn’t see any for sale. Breakfast was the usual continental spread, but it was always stocked and staffed. We’d stay again.

The building seemed old and historic, with limited access, and it smelled that way too. Still, the way check-in went was the last straw. I asked Juan at the front desk about parking only after we’d checked in, and he then told us there was none on the property. We’d have to park several blocks away for $15 to $45 a day. He offered no help with finding a solution and seemed bothered by having to check us in at all. We canceled and left. We were glad we did, since we found a much better place within minutes.

The milk at breakfast tasted sour, and to me it was clearly spoiled. We told the breakfast staff member, but she seemed indifferent at first. We said it had gone bad and asked her to taste it. After we poured her a cup, she only looked at it and said it was “regular.” As far as I know, sour milk means it has spoiled. That was disappointing, especially given basic food safety expectations.

We’ve stayed at Westwinds Inn at least four times in four years, and it’s still our favorite little hidden gem in Key West. The two heated pools feel like a private backyard oasis, and the beds are super comfortable. Every room we’ve tried, four styles so far, has had its own personality. Everything is always clean. It’s four blocks from Duval Street, and being able to park our rented golf cart right on the property is a huge bonus. Breakfast is a small continental spread, but sweet, and the women who run it are lovely. The furniture doesn’t match and nothing’s shiny and new, which is exactly the charm. It’s cozy, quaint, and ridiculously comfortable. We won’t stay anywhere else. I’ve seen the negative reviews. If you want a crisp, modern, Instagram-perfect new hotel, this probably isn’t your place. There are plenty of shiny new ones down the road. But for charm, comfort, character, and that laid-back Key West feel, Westwinds is it. 10/10, highly recommend. We’d stay again and again.