Wondering where most of you parked your rental cars when staying at Heron House. They said there was residential parking (free) nearby or a lot for an extra $15 per day. I'm guessing the street parking could be busy or have restrictions on how long you can park - but maybe not - anyone know?

Residental parking is for residents who have the proper tag. Lot parking is expenisive. Meters are 15 minutes for .25 and cops love to ticket there. Be careful.

Get rid of the rental car. You wont need it. The Heron House is perfectly located in town.

So would you return the car to Key West airport, then take a cab to the B&B and repeat the steps on departure day? Just seemed like some trouble to go through, but maybe the KW airport is very convenient? (never been before)

I agree with the poster who suggested ditching the rental car.
You will not need it. HH is very close to everything, and for places too far to walk - a couple of the restaurants - you can take a pedicab (basically a bicycle rickshaw) which is fun and a neat way to whiz through the back streets.
The airport is only a few minutes away, and then you don't have to worry about driving and parking (we've done it, but wouldn't again).
Have fun - I'm jealous

The trouble is finding a place to park and remembering to feed the meters in that town. The airport is small and very easy to get around. I agree, get rid of the car.

Thanks to you all - I found a direct flight to Key West out of Atlanta on Delta, so I changed my travel plans to fly directly in! The only downside is that I have to leave early on Sunday morning, but it also means I have 4 more hours on the day of arrival so it's a great trade off in my book. 4 full days with no car seems like heaven to me.

The idea to nix the car is a good one. We stayed at the Heron House on our last trip to Key West, and rented a car just one day to take a drive through some of the other Keys. We got back too late to turn the car in that day so we paid to park in the lot you are talking about, which is just a block from the Heron House. The Heron House is right in the middle of town, and most every thing is within walking distance. If you prefer not to do a lot of walking, there are plenty of bicycle and scooter rental places where you can rent something to help you get around the island.