Beach House, like Windward Pointe is not located in Old Town. So you definitely need some type of transportation. Parking is a pain in Old Town and there is no free parking anywhere. So some recommend using rideshare to get around. When we were at Windward Pointe, we mainly stuck to the resort. We did take some scenic drive and two of our seven days we rode the Old Town Trolly. This was our transportation around Key West and we didn't have to deal with parking. For us, the closest trolly stop was at the Hampton Inn right next door to WIndward Pointe. If you go this route, stop 7 of the trolly should be a short walk from Beach House.
My husband is handicapped so we will be driving down from MA and will have our handicapped placard. From what I read, I think we can park anywhere for free. We are more interested in handicapped access. He can walk very short distances with walking sticks though and he does not need a handicapped bathroom.
So restaurants with outside seating and room for a scooter are ideal suggestions.
While in our 50s, late nights are not our thing. Usually in bed by 10 and two cocktails are just about our limit. We love live music, but not real loud. My daughter graduated from Berklee College of Music and we appreciate good musicians, but not the late nights.
How were the noseeums at Winward? I was glad we didn't match that after reading reviews.