Honestly, Ice Bar is a tourist trap. For what it is, it's not worth it. Grey Goose lounge above Amway is kinda cool if you haven't been, and there's no cover.
The Ravenous Pig is great, as is their sister company, Cask and Larder. Good luck getting a reservation there for V-Day though. SEA Thai is excellent!! A nice spot on Park Ave in Winter Park is El Bodegon. Traditional Spanish Tapas. Prices are decent and food is great.
Personally, I usually grab some nice steaks and lobster tails and grill them for my girl. She loves it and we get to avoid the V-Day waiting and crowds. I usually take her out to eat often anyway.
Good luck OP