It can be pretty hard to find the right place for groups over 16 people. What others have done in the past is rent two houses near one another. Another option is renting one house and then a bunch of hotel rooms. This way, everyone can come over during the day to hang with the crew yet go back to their hotel or the other house to sleep and chill. If you plan many activities such as a yacht party, brewery tour, or winery tour - you can get a bus or limo big enough for everyone to be together.