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Welcome! If you are not an owner at Harborside, then the earliest you are allowed to even try for a reservation is 8 mos. out. Only Harborside owners can make a reservation between 8 and 12 mos. out. We are already within 8 months, so you can call now.
For lots more info. about how Starwood works, see the Starwood FAQ at the top of the board.
Usually your season corresponds to demand (e.g platinum week = high demand week). However, that's not always the case. For instance, Hawaii properties are all platinum weeks within Starwood, but July is in much higher demand than October.
Generally speaking, warmer locales are in higher demand when the weather on the mainland is colder. And almost all of the timeshares (except the desert ones) are in higher demand in the summer (when the kids are out of school) or when there's a Monday or Friday holiday (because working folks only have to take 4 days off of work to enjoy a 9 day vacation.
February is Platinum season and pretty high demand--I think you would be pretty lucky to secure something at 8 months out as at that point you are in competition with every other Starwood owner who can call for Harborside at that point.