This charming heritage property on the National Register of Historic Places has barrels of colonial charm but has been updated for the modern guest. The rooms are comfy and understated, yet luxurious, although some rooms are appointed oddly, making them feel a little small. Not all have sea views, so make sure you ask for one when booking. The Hilton group who manage the property has a good track record for being gay welcoming. There were plenty of other LGBT guests – Key West is quite the gay destination – but also plenty of straight honeymooners and families.