Boston Nesties
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Not sure that you would still be checking your Key Largo post below, but I would DEFINITELY recommend Key West over Key Largo if you're looking for nightlife. Key Largo may have a better beach, but there is so much more to do in Key West.
That being said, H proposed to me in Key Largo while swimming with the dolphins, so it will always have a special place in my heart... but for a fun girls weekend, definitely go to Key West! If you want tips on what to do, let me know... we just moved from South Florida (Fort Lauderdale area) and spent some time in the Keys.
Re: **Rynna**
I wouldn't say Key West is in any way sketchy... it's kind of a laid back place with LOTS of tourists, so I'm sure some sketchiness does occur, but I wouldn't say it's unsafe. I will say, though, most of the things in Key West that are fun to do are not directly on the beach/within walking distance. You'd want to stay in town for that.
If you want to stay on the beach to walk to stuff, I'd go with the other recommendation of doing South Beach. Lincoln Road is a blast with lots of great places to eat, and there are a ton of bars/clubs within walking distance. Plus the beach is awesome. You're going to find the best of both worlds there. Key Largo has great beaches/outdoorsy things to do; Key West has awesome nightlife and tons of fun things to do during the day; South Beach has all of the above.