Key West is a very small island, but it is a big tourist destination so the amount of places to stay at is truly endless. We do not have a hotel block and a lot of our family members are staying at timeshares or houses they rented on Airbnb or VRBO. I recommend searching a few travel sites to get a feel for what you would like. If you stay in old town or near southernmost point, your prices will likely be higher but those areas are more walkable to stores, restaurants and bars. If you stay in new town or in the front of the island by the bridge, your rates could be less but there is not as much in walking distance and you’ll need to taxi, uber or rent a golf cart or moped to get around the island. Alternatively you could drive your car around the island but I will say that parking lots can become costly. Plus you don’t want to drink and drive in Key West, this is why we rented the conch trolley train to transport everyone to the wedding and reception, so you can drink and have no worries. On this page I will post some of the places I’ve come across or have stayed at but a quick google search will open you up to more options.