I haven't stayed at the DT, Casa, or Reach, but I've wandered around all 3 and I'd recommend the Casa Marina. The DT is not in a very good location and is a farily typical FL Keys large hotel. The Location for the Reach and the Casa is much better. IMHO the Casa has a much nicer ambiance and layout, and is much more elegant than the Reach.
I have a reservation at the Casa Marina for April. I Just looked at it on line and noticed a button stating "Request Discounted Room Upgrade". I clicked on the link, and sure enough it took me to the NOR1 fee based upgrade system page
. Its my first stay there so I'll be very curious how they implement the My Way Diamond preference choices for W=A properties:
1) One category room upgrade (excludes suites and the Napua Tower at Grand Wailea and the Imperial Floor at Rome Cavalieri). If room upgrade is not available, you will receive both of the remaining options.
2) Discount at select resort facilities (may include spa, golf, restaurant, etc.) OR access to the Colosseo Lounge when staying at Rome Cavalieri OR when staying at the Waldorf=Astoria hotel in New York City, a choice of either a full breakfast each morning or two complimentary beverages each night of the stay.
3) 1,000 Hilton HHonors bonus points
Based on this its a guess about what Diamond bennies (if any) will be offered at the Reach or the Casa Marina.
If you can wait I will be posting a Casa trip review late in April.