USVI-On-Line

This one is a two bedroom that made my final list during my search
http://www.vrbo.com/176773

This one is on my short list for 2 couples:

http://www.vrbo.com/254704ha

I like that the bedrooms are in different buildings, nice privacy for couples

michigan girls, Fair Winds is definitely on my short list. It looks divine.

Great location, close to Cruz Bay. Incredible views! The price is in your range...
http://www.vrbo.com/482502

Full disclosure: We own it!

Check out Private Homes they have several in your price range.
Some places do not have AC.
Mary-Eileen is great to work with at Private Homes.

High or low season?

If low, these fit your budget:
Dreamweaver: http://www.vrbo.com/437645 Ajax Peak, 2br/2ba with lofts, hot tub, solar
Villa Calabreeze: http://www.vrbo.com/256170 Coral Bay, 2br/2ba (this one is close even in high season)

We're booked! Had to create this silly ticker to stop the tears of gratitude sliding down my face. THANK YOU all for your advice, it made finding the villa an adventure and I'm grateful to all of you for your help. Put in a request for the Banana Cabana today!

Tickers are NEVER, EVER silly! Congratulations!

Interested in hearing about Banana Cabana. Where is it located? Where did you find the listing? Would love to take a look at it.
Hope you have a wonderful trip to paradise.

Thanks silverheels! Banana Cabana is located in Coral Bay, about two blocks down from Skinny's. I found them on VRBO - here's the link: http://www.vrbo.com/212678

The villa is organized into 2 "pods". I'm traveling with my boyfriend and another couple so we liked the idea of having some space while traveling together. It shares a pool with a few other villas. This is my first villa with a pool so sharing doesn't bother me. And the price was fantastic - less than $1,500 for the week. So far, the Windspree folks have been very responsive to my questions, and I'm looking forward to staying there!