If by winter break, you mean Christmas or New Year's weeks, then you are unlikely to be able to get 3 to 5 units in a bulk spacebank. The large systems which practice bulk spacebanking tend to keep these prime weeks for their owners to reserve. For this time period, I would suggest Holiday Inn VC aka Orange Lake or Sheraton Vistana Resort (no water park but plenty of activities) or perhaps Cypress Pointe (no water park, enough activities to keep teens/kids busy and walk to shops, restaurants nearby). I've seen numerous deposits from these resorts for holiday weeks. Make all requests as close to 2 years out as possible and you'll have an excellent chance of getting everyone into the same resort, trickling in over a few months. Be prepared for sticker shock on the amount of points required for a 2BR Christmas/New Year's week in Orlando.
If by winter break, you mean Presidents week in February, you may be able to snag a bulk space banking bonanza. Enter requests around the same time as each other so they will be close together on the waitlist. Request one resort within each of several large systems that practice bulk spacebanking. Then, as the first system makes its bulk deposit for your time frame, you have the best chance of all getting a match for the same resort. If only some match, the holds may be dropped without a fee and that resort removed from all searches. The next resort to bulk spacebank may be more successful. By only including one resort per system, you avoid matching to different resorts when a system makes its bulk deposits. For a February week at a resort which bulk spacebanks, I would suggest Wyndham Reunion (nice water park) or Hilton GVC at Sea World (no water park but plenty of activities). Other people may suggest more to add from other systems.
