Portland International Jetport, Maine. Boston is further away but consider renting a car from there or taking the train for lower prices.

Yes! Feel free to share cars with family - once you're on the island you don't need to drive much but getting out there requires a car.

Yes! IMPORTANT: For an AirBnB or VRBO, make sure to check driving directions to Harpswell Island Rd, Orrs Island ME as some locations like Harpswell Neck or Portland will appear close in Google searches even if local geography makes them an hour + drive away.