I'm going to Islamorado with my teenage son and an adult friend to scuba dive and relax for 3 days at Thanksgiving. This is our first time in the middle keys (been to Key West). We've heard that Islamorado is nice, and good for diving. It seems to be hard to find a reasonably priced hotel room that's within walking distance of a beach. Our price limit is $150/night. We're not interested in a room that fronts on a mud flat, which most seem to do. Location is everything, we don't care about the condition or age of the room.

The other adult doesn't dive and just wants to sit on the beach.

I like this place:

http://www.lookoutlodge.com/index.html

We stayed there last year. It is on the west side of the road, so great sunsets. The rooms were nice but not over the top price wise. It has a manmade beach like area at water's edge which was nice for relaxing but it's not a real beach.

there was however a real beach right next door that was available should you need to walk from the shore into the water instead of climbing down steps.

After posting that reply, I feel that I wasn't strong enough in my endorsement. If they have availability, grab it. We had a great time. There is dockage so a charter could pick you up if you could arrange it.

There were a couple of grills should you choose to cook out and lots of great food nearby.

Islamorada's only beaches are miniature and man made. The Hampton Inn has a nice pool/man made beach setting with 2BR units available. Walking distance a good restaurant, Lazy Days. The nearest sizeable beach would be Sombrero in Marathon, probably 45 minutes to Islamorada.

Seconding Hampton Inn. It is not your average Hampton Inn.

We also stayed at the Hampton Inn and loved it. It's a nice property on a very nice beach.

Thanks Notbob, Stumpworks73, Ackislander and Montereybob. Very helpful.