Could it be possible that the old-school snowbirds are dying out? I mean, we have the same thing here on the Resort coast of Kohala. The same people coming year after year to the same rental, booked a year in advance. The “Same Time Next Year” scenario (without the affairs of course. 
) Funny how you have the activities of the guests fine-tuned to a science… and that tells you so much. Will hipsters have dinner at five? Will Millennials fish or golf all day? The times they are a changing!
My good friend is an old school property manager who has booked Kohala Coast vacation rentals for three decades here on the Big Island. Long before there was Air BnB or VRBO or FlopKey. I think even she is seeing a drop in bookings, but not because she’s lost business to the Internet platforms. A lot of her clients are super wealthy (the kind with oceanfront homes) and don’t want to bother with the day-to-day slave plantation work that you and I do. They do book on Air and want her to manage the rental and she gets a cut. She’s made the new model work for her and got rid of her bricks and mortar vacation rental office. In order to manage more than one property in Hawaii you need a real estate license. This gal has seen it all over the years. She sees the crap we are talking about here every day and three times on Sunday, and in my opinion, more than earns her commissions.
I cannot understand this… other than to think that the mild Northeast winter has people jogging in Central Park in shorts instead of thinking about escaping the cold in Florida.
Winter misery is a sincere driver of business to Hawaii. Consistently in the winter Hawaii hands down has some of the most perfect temperate weather on the planet this time of year.
It doesn’t hurt that it’s got gorgeous natural beauty too.
Sands of every color–black, white, mixed, gray and even GREEN… Gorgeous, healthy coral reefs laden with colorful reef fish, turtles everywhere, a rich, engaging cultural history, fresh fruit and locally caught fish, friendly aloha spirit, and an active volcano on the other side of the island. The world’s finest observatories atop one of the highest mountains in the world. Come visit Hawaii Island, the land of adventure! 