As cool as the drive to Key West is, it's a long way. We are going for four nights/three days end of February/beginning of March and opted to fly down and back. Key West high season is pretty pricey when it comes to lodging and our timeframe is high season. Given that we opted for the Best Western Hibiscus (pool view - double queen room) // includes a continental b-fast, mini frig and microwave in room. With tax we are paying $323 a night. The real plus about this is that it is walking distance to old town, so we don't need a car and can walk everywhere. This motel is one of the less expensive options that is well reviewed on trip advisor that is walking distance to lots of the attractions in old town/Duval street. Many people like to do bed and breakfast's in Key West too and some of these are some of the more economical options in Old Town also. We wanted a double queen room, so that limited B&B options, but there were some. But then we also wanted our own mini frig and microwave and we didn't find any B&Bs with that. DS is a picky eater, so a microwave and mini frig our own snacks, etc. is a really handy option. Also, he'd eat the Best Western continental B-fast food, but not the slightly more gourmet b-fast offerings at the B and Bs. That made this an easy choice for us. There are tons of great restaurants that we have heard about and see that will work great for both the foodie and picky eater, so I think this will work well.
Do note that prices vary a lot based on time of year, but Key West has gotten to be very popular, and I and many were quite surprised at how pricey lodging is, especially when you compare it to some place like Orlando lol.
Our stay will be pretty relaxed with pool time etc.
We on the mini stay plan to:
Day 1
do the trolley tour
do the Hemmingway house
Pool time
Hit Duval in the evening for dinner
Day 2
check out the Southernmost point sign
Butterfly Conservatory
West Marlo Towers and Gardens
pool time
Commotion on the Ocean Music Sunset sail
Day 3
Fort Zachary Historic State Park
We plan to do the 11 a.m. tour of the fort there
Then check out the beach and have lunch over there
Some pool time
Hit Duval in the evening for dinner
Please note that Key West is NOT known for it's beaches. It's known for a cool laid back vibe, but there are much better beaches elsewhere in Florida. We aren't beach people. Maybe that's why we usually when we go to Florida go to Orlando. As non beach people for the most part, Key West should work well for us, and in fact we are doing a mini trip there instead of a mini trip to Orlando in 2018 / no Orlando for us next year.
Hey, though, in November this year we will be hitting Orlando -- less than a month away for our mini trip there.