Originally Posted by pinniped

It's been a while since we've gone down to Key West, but the one thing I learned over the course of a few trips there is that the hotels generally are underwhelming outside of the top luxury properties.

Late 90s - stayed at a crappy Marriott. It's no longer a Marriott...no idea what it is now.
Early 00's - stayed at an adequate but overpriced Westin. No idea if it's still a Westin.
Also had 1-2 trips in Holiday Inn type joints that were literally Motel 6 quality anywhere else in the country.

Then figured out that VRBO rentals are better. Did a couple trips where we rented small 1-bedroom cottages. Did another where 6 of us rented a 3-bedroom house. All significantly better experiences than hotels. We walked everywhere on the island...didn't seem to matter too much exactly where your place was, as few places were directly on a sandy beach, yet everywhere is a short walk to one.

So if I went back to KW today, I'd probably start with VRBO and maybe look at Airbnb as well.

5 nights feels long for KW. Maybe 3 there (with or without the Dry Tortugas trip) would be sufficient for me. That, combined with the fact that none of the Hiltons are great, would lead me to save my points for something else.