Just returned from a week in Key West for the powerboat races. This was our 3rd trip to KW. On this occasion we opted out of staying in a hotel and rented a condo. It worked out well as we had a full kitchen and grill so that we did not have to eat out every meal! I cannot recommend the Shipyard Condos enough. If we ever go back we are definately staying there again! We rented through: http://beaconman.com/Islandnomade/ We stayed in the Villa Nomade and our friends were in the Villa Soliel. Both were 2 bedroom units. Absolutely spotless and well apportioned. For $1400 total for 2 couples for the week it was a pretty good deal as Duval St was just a quick 5 minute walk ($1200 on non-race/FF weeks). I made it walking from Mallory Square back to the condo in 10 minutes. GREAT location! We also liked that our units were not right on the main street - so it was very quiet. Of the two, I liked Villa Nomade best as it had a really nice garden/deck area off the back.
We had drinks with friends at the Parrot Bay Resort which is a good distance from downtown (you would have to rent a scooter at the very least to get down to Duval St.). I would definately consider staying there. The grounds and pools are simply gorgeous! Friendly staff and seemed very seculded even though it was on the busy state route. If you are familiar - it was where the old Hampton Inn was by the Walgreens and across from the big grocery.
We rented 2 bikes and a scooter for the whole week. We used A&M Rentals. They will drop off to any KW location. We rode the scooter a good deal. We just returned when we needed a free gas fill up. Very convenient. We booked about a month before the trip as we were told that scooters sell out on weekends during the races (coupled with the cruise ships being in!). Overall, would definately use them again!
As always - very hard to return to the "real" world - especially back to the cold north! Thanks to everyone for their posts. It helped plan - once again - a flawless trip. Happy Travels!