Family of five, with two in college at the moment so we are at that age where we have been traveling with boyfriends and girlfriends lately. We are also Florida residents who live just far enough away that we typically stay for at least a long weekend. I'm totally cool with getting two rooms and my own kids sleeping in a separate room. However, when the boyfriends or girlfriends join us this won't work for my comfort zone. I much prefer everyone under one roof when we do these types of trips.
If you find that a 2 bedroom on site is out of your budget. I would consider Bonnet Creek or Windsor Hills. Rent a car because the buses are not that great if your use to Disney transportation. Yes, this will be a different type of trip than your use to, but there are some perks in condo stays that being crammed in typical hotel room won't give you. For starters, for a party this size even with a car rental and parking it's probably going to cost less. You may even be able to get a three bedroom, 2 bath unit in your budget. You will have full kitchen so you can do easy snacks and if you want some easy meals in the condo as well. Having a washer and dryer is really nice. (I read you guys are doing a cruise as well so the washer and dryer in the condo is wonderful for trips like this.) Space with teens is always a good thing! Also, if you rent a car consider renting from a company that has a location near the port and arrange for drop off there. In Florida they do not charge and extra fee for drop off at a different location than where you pick up the car, but do let them know this is the plan when you book. For Five people the cost of Disney transfers from resort to port and back to the airport may actually be about equal to what a rental car wold cost. It's a very easy drive from the Disney area to the port, but do take small bills and quarters for the toll roads.
I know your probably considering The Double Tree in Disney Springs for the 60 day fast pass window. I guess I see this point, but we hardly ever do our fast passes 60 days out and still manage just fine. If your really freaked about this book your first night onsite at what ever an onsite is most cost effective for you and then move over to the condo. That way you you can book your fast passes at 60 days out and still have the comfort of the space you need. We have stayed at the Double Tree in Disney Spring an while its okay, clean, safe and staff is nice it lacks anything exciting and the pool is basic and boring.
Best of luck in what ever you decide. Enjoy your vacation.