Actually, we already have reservations set for the next day so we were going to rest and take a nap during the day at our hotel. Basically, we will pretty much be staying up for the night and taking in the sunrise after the drive. But if the drive is dark and dangerous (and trap for speed tickets) we were going to bite the bullet and get a place in Ft Lauderdale for the few hours but to me it didn't seem worth the money when it could go towards rest of our trip...

There are plenty of low cost motels about 4-5 hours before you get to Key West. I would highly suggest staying in a place closest to the airport. The drive down is not under bright lights and wide lanes, and you would be missing the incredible views of the water that you'd get during a day time drive.

The speed limits change all the time and on several Keys there might be a black and white ready to pounce.

Driving straight to Key West might mean an unsafe trip and if you get there first thing in the morning you'd still have to wait until about 3 PM to check in to your Key West room.

For sure, get a room in FLL. I regret not doing this 3 weeks ago.

The drive is down right dangerous at night after a flight.

I would get a hotel/motel near the airport. The drive down is part if the experience. It is a drive that needs to be done during the day. If you are looking to watch $ search out cheap rooms around Ft. Lauderdale.

Get a room on priceline or hotwire either near the AP, or along your way (ie the first hour or so no more).

Should be easy to find one a lot cheaper than that. the dirve is long and not very safe if you are tired.

I've done the drive down overnight a handful of times. I wouldn't say it's dangerous but I know the route well. There's enough light, or ambient light, most of the way. The only thing I would recommend is to make sure your co-pilot promises to stay awake the entire trip. One time my wife fell asleep around Key Largo and I had a long couple hours in silence. Not good that late at night.

Chances are you couldn't check into your hotel in KW until close to 3:00.

It's not that bad of a drive, dark and boring - yes. But dangerous, not really anymore then any other dark highway at night. We've found decent rates at the Sheraton near FLL. Under $100 at times.

If you do drive be extra careful and watch out for Key Deer they are small and hard to see. Be devestating to hit one of those cuties on your vacation.

I've done the nighttime drive many times as well and don't think its dangerous. Like Blue and Bumpy said, dark and boring but not really dangerous. There are speed traps like on any stretch of road so watch out for that. Its doable, but I think you'll miss so much if this is your first time in the keys. You can get a room in Florida City for around $100 a night then make the drive in the morning when you are refreshed from the trip and its bright and beautiful out. So many things to see and do along the way, it would be a shame to miss them.