After a few months of reviewing the available resort options on the islands, we decided to go the "condo" route. Yuko and Bob were delightful and accommodated us in every fashion.
Here is how they sold us on the rental:
Location: Cowpet Bay is one of the cleanest, most secure (gated property with night guard), and prettiest locations on the island. The beach was in walking distance and offered recreational craft rentals, two tiki-type bars, a mini-stand for beach essentials and a higher-end dining restaurant. The Ritz-Carlton was also a very short walking distance so access to their spa and other services were easy to come by.
Transportation: We initially planned to rent a jeep for the week but thank goodness that idea didn't work out. The roads are vertical, narrow, and driving directions are flipped (like those in Europe) and if you are a first-time visitor, I seriously suggest cabbing it. What would have cost us nearly $400/week + gas (it's almost $5/gal on the islands) was scrapped and we were able to get around for $20-30 in taxi fares a day - that included both of us. The locals will even loan you their personal vehicles for a day should you feel adventurous - at a low fee - and that was something we didn't explore but Bob had that option available to us if we needed it.
Condo Amenities: We had WiFi, a tv with cable, a large balcony with ocean views, plenty of fresh linens, pantries stocked with cleaning supplies, cooking utensils, air conditioning, a new washer and dryer set, ice chests, and the list goes on...everything was furnished lovely and was very clean and the kitchen featured all modern appliances.
Now for some tips:
Local Pests: The island has bugs or so we learned to call them, "no-see-ums" (basically sand fleas). Do not use any type of scented lotions or oils and carry bug-spray. Gin also works - enjoy a shot then rub some on your body - it will kill the oils and the scents and you will become invisible to these pesky buggers.
When visiting Red Hook: This is about a 5-10min drive from the condo. Tons of shops and local dives like Fish Tales and XO Bistro. The ferry dock is located here - take a day and travel to St. John and visit Truck Bay and Cinnamon Bay.
When visiting Charlotte Amalie: 15-20min drive and packed with shops. Don't stay down there after dusk. Barter but be polite and the best deals happen when the cruise ships are NOT docked. Highly recommend EFEY and Little Switzerland for jewelry.