I know it's crass, but here's a plug for our own house! You said you wanted to be closer to Cruz Bay, but after 20 or so years of St. John visits, we decided that it was Bordeaux Mountain or nowhere! So we bought land and completed our house three years ago. The road up is now completly paved and ou...

Check out this one: http://greatcaribbeangetaways.com/skyflower.htm
Very private, paved road, flat driveway, hot tub, and unreal views!

Check out Skyflower on Bordeaux Mtn. Wonderful house. Unbelievable views. Reasonable prices. Paved road all the way, and a nice level driveway. Google Skyflower VI.

One rental agent/property manager not mentioned is Great Caribbean Getaways. We use them now for our own house (Skyflower), and had used them for 18 years when we were renting other houses. Nice to deal with, good listings, take wonderful care of their properties. We are totally pleased.