@Laura2592 "Guests don't read and they may believe they are getting ALL the houses for the price of one, "
But if there is a separate listing for all five, the price for that would be clear on that listing. So regardless of whether they read or not, the price for all five would be evident when they fill out the booking form.
@Chelsea325 I don't know your area, so hard to say. Some market research might tell you if people tend to look for places in your location that accomodate larger groups, or whether plenty look for places that accommodate 2. Laura brings up an important consideration re parties, but it's possible to market things in such a way that it is clearly for family retreats, not partiers, but you would want to vet guests carefully, so it wouldn't be a good idea to use Instant Book but require guests to send booking requests instead, so you have the opportunity to dialogue with them before approving a booking.
Only listing them individually would certainly be easier to start with, and the thing is, you can always add the entire property option after you've been hosting awhile and learn all the ins and outs of it. It can be a big learning curve.