Ron and I went to Key West, FL for a week at the end of August - through first week of September. Ron finally got his HOT vacation and without any hurricanes. Since hurricanes do hit the Florida Keys at times, we had purchased vacation insurance. It wasn't expensive and the peace of mind of knowing we wouldn't lose our banked week and would be reimbursed for flight cancellation was worth it.
We flew into Miami and spent one night there before picking up our rental car and driving to Key West. After a couple of hours, we finally got out of the stoplights (we chose to avoid the toll highway so don't know if it had as many signal lights as the highway). Once we got to the Keys Highway, I was impressed - so many miles of highway with the Atlantic Ocean on one side and the Gulf of Mexico on the other - and passing through towns that I had read about and seen in movies (Marathon, Key Largo, Islamorada). But after 20 or 30 miles, enough is enough. We did stop and had a great lunch with conch chowder in Key Largo.
If I were to go again, I'd fly into Miami and then take the new ferry that goes from Miami to Key West in less time than driving. You really do not need a car in Key West - in fact a car is more of a bother. The roads are narrow, and there is little parking (what there is costs a bundle), plus you can rent electric two- and four-passenger buggies for any time you want to leave the immediate downtown.
We stayed at The Banyan Resort, which is lovely - a collection of nine historic homes restored and converted to condos. The homes are grouped around gardens (with the lovely old banyan trees for which it is named), patios with barbecues, two pools, a hot tub (that we never used as we were already hot) and a snack shack/bar. We were lucky and got a one-bedroom condo on the first floor with a front porch which we used and a back porch that we didn't use but could open up for a pleasant cross breeze. Some condos were on second and third floors with no elevators. Our condo (small but well-designed) had a living room with dining area (glass table with four chairs), the kitchen area along one wall was well-supplied with dishes, pans, knives, cutting board and every convenience (such as microwave, toaster, blender, etc.). The living room TV was above the refrigerator (facing the couch). The refrigerator was full-sized with an ice machine. The bath and bedroom were nicely furnished, and all was very clean. The reading lights even had plenty of wattage so we could actually read in bed.
The resort also rents out their condos. There are parking fees charged and different levels of fees for maid service depending on frequency requested. The resort is on a quiet street about three blocks from Mallory Square (where there's a sunset party every evening - rain or shine) and one block off the major shopping/bar/art gallery/happening street. It is just a block up from President Truman's Little White House (wonderful tour with videos), the Audubon Museum and garden, and about three blocks from Hemmingway's House (take the docent guided tour - you learn much more than just wandering on your own).
Ron had been asking for a hot vacation and finally got his wish. The weather was hot and humid - what I expected, and I will say that I found myself in a few stores, bars, and art galleries simply because I felt a cool breeze while walking past the door. We found that we enjoyed meandering and visiting the various sites and galleries in the morning, returning to the resort to enjoy the pool, read, and visit with the other guests in the afternoon and then back to Mallory Square for sunset drinks and watching the various street performers.
The first day in Key West, we took the Conch Train to get our bearings and hear some wonderful history and stories about Key West. It's well worth the $20 price. (If you have the Miami Entertainment Book, you'll find several good deals such as 2 for 1 for the Conch Train as well as 2 for 1 entrance to the Truman White House.) After the Conch tour, we walked to different places on our own. The one day that we did drive, we went out to the various beaches, stopping at the Southern-most Point of the US for a mandatory picture - then settled on one Atlantic beach and spent the day enjoying the beach and the ocean. I still can't believe how warm the Atlantic is in that area! I think it was warmer than our pool at the Banyan!
Restaurants and bars were almost every other building. We found Crabby Bill's to have some great happy hour prices - two dozen oysters on the half shell for $5. We also ate well at Billie's, Pepe's, and Sloppy Joe's. Had some great barbecue at the Meteor Smokhouse. And, of course, we stopped in for margaritas at Margaritaville.
We enjoyed the laid-back and tolerant attitude of the town. I'm so glad that Ron got his hot vacation - and that it was one that we both enjoyed.