There are LOTS of small places to rent right on the beach in Grand Case. Most of those, you can walk to dinner without any problem and there are lots of high end places in Grand Case, but many that aren't, also. The only problem with walking in that area to dinner is that if you are up around the bend there, where Le Petit hotel is, for example, that there are no sidewalks and it's kind of dark, and you'd have to walk in the road. In the main part of Grand Case, it's pretty well lit and you are fine walking there, so long as you just pay attention looking for cars. There are also a ton of places in Orient Village where you can walk to dinner without any problem. Personally, for your criteria, I would eliminate the places in Basse Terres, and in Oyster Pond, as you could not walk to ANYWHERE from there. And if your main emphasis is going to Orient, you should probably stick to Grand Case or Orient Village. All of that said, it depends also if you are only going to go for nightlife once in the week, as you stated. If so, it would be fine to stay in Orient or Grand Case. If you are wanting to go 3 or 4 times in the week, then there are lots of places along Simpson Bay where you could walk to dinner, or at least, have a very short drive, and you would be close to nightlife.