Can't remember name of B&B

Question

I used to visit KW regularly. I was even considered as an "expert"

Anyhow I forgot the name of the great b&b where I stayed (very close to Duval and the water.

They offered free bikes, breakfast,happy hour, a pool and a couple of Schipperkee dogs.one had gone missing. Any thoughts?Went to a couple TA happy hours. Trolley driver, Dave? Was very helpful.

Answer

This is a tricky one — I wasn’t able to reliably identify a B&B in Key West that clearly matches *all* of the details you remembered (free bikes, breakfast, happy hour, pool, and Schipperkee dogs). That said, I found a few properties that share *some* of those characteristics, plus some thoughts and follow-up questions — and a few possibilities based on memory and B&B options in Key West.

Here’s what turned up from research + some analysis:

The Mermaid & The Alligator — This is a B&B / inn in Old Town Key West with a pool, complimentary daily breakfast, and evening wine hour (“evening wine” is listed; sometimes this could be considered their “happy hour”). Consistent with some of your memory: breakfast, happy hour, pool. But: I did *not* find mention of free bikes or pet dogs on their website or in standard listing sources. Their listing in B&B directories makes no reference to pets.
Old Town Manor — This is a Victorian-style B&B on Eaton Street in Old Town Key West. However, I found no documentation that they host pets (especially not Schipperkes), nor that they provide free bikes or have a pool + happy hour, at least in their public profiles.
Duval Inn — According to the Florida Keys destination guide, the Duval Inn offers “complimentary island breakfast and happy hour, tropical gardens, heated pool.” This is promising — breakfast, pool, and a happy hour match part of your memory. But, again, I found no place listing free bikes or resident dogs (especially Schipperkee).

Based on what you described — *free bikes, Schipperkee dogs, a full dessert-style B&B vibe with happy hour and pool* — I didn’t see a current, well-known B&B that exactly matches all of that in publicly available listings or B&B directories. That suggests a few possibilities:

You might be mixing up some memories — possibly combining features from more than one place, or maybe from a property that has since changed its pet policy or amenities.
The B&B may have been a very small, independently-run guesthouse (or an Airbnb-style setup) that isn’t well-documented in large B&B databases anymore.
Some guest memories (like the Schipperkee dogs) might be anecdotal and not in the formal property listing.

My best educated guesses based on your memory:

The place might have been Duval Inn, because of their happy hour + breakfast + pool, and its location is quite close to Duval and the water.
Another possible candidate: Key West Harbor Inn, which is in a historic mansion, offers breakfast and happy hour. According to Mallory Square’s B&B listings, they provide “complimentary breakfast and happy hour” and have bike rentals.

Given that you remembered “Schipperkee dogs” (that’s very specific), I would suggest a couple of next steps:

Check old trip photos / emails / booking confirmations — any reservation site or email history might give you the name.
Post in a Key West–specific travel or local history group / Facebook community and describe what you’re remembering (amenities, location, details like the dogs). Locals or longtime visitors may recognize exactly which B&B had Schipperke dogs.
Call a few B&Bs on the island (like Duval Inn, Key West Harbor Inn, and others) — even if current policies have shifted, staff may remember past pet / bike setups or historical notes.