You tagged Curacao and I think that would be a good fit for what you described. We stayed at the Lio

I'm after a lively island with nice beaches that has a tropical feeling. Ideally a place that isn't full of mega resorts and has a good beach bar scene at night. Im not too fussed about clubs, just as long as there is good outdoors leeds hotels entertainment at night.
Unfortunately, "good outdoors entertainment at night" leeds hotels usually means the islands that are busier, sometimes meaning bigger resorts. The more quiet laid back the island, the less nightlife you will find. There needs to be a happy medium somewhere.
You tagged Curacao and I think that would be a good fit for what you described. We stayed at the Lion's Dive. There are 3 restaurants on site and several more within walking distance. Hemingways bar was the place to gather at night for drinks and conversation. Down the way at Moomba's was more lively if your are looking for that.
We went in a May and it was not crowded at all. Only handful of kids. They offer 2 bedroom condo type apartments, which would work for you and your friend. They were constructed in 2009, so still fairly new.
What I was getting at is that I went to Barbados for example and wasnt impressed at all. The vegetation didnt have a tropical feel and I read somewhere that due to the differences in weather leeds hotels the vegetation can vary quite heavily from island to island...
What about St.Kitts? the beach at Frigate bay has a quite a few beach bars, Ziggy's stays open til the last person leaves There are some other lovely beaches (south friar beach with Shipwreck Bar is my fav) with nice laid back beach bars as well.