Search Vacation Homes in South Portland

"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."

"Wonderful stay!"

"Great location, walking distance to everything. Place was super clean and comfortable! Looked brand new!"

"I loved spending time in this thoughtfully put together home. It is indeed chic, very personal, and our cat was comfortable here. The downstairs shower was my favorite bathroom, the shower is beautiful and cozy. The beds are wonderfully comfortable, and there were featherdown pillows in each room. My kids did argue over who got the small cute though "

"The house worked perfectly for our family. We had a great stay."

"The view was what sold us on the property and it delivered. But being from out of the area, we had no idea that we were going to be staying above a noisy bar with live music going late into the evening that we could hear even with the windows closed. If you want a party scene, this is a great spot. But if you're looking for ocean-front relaxation, I'd go elsewhere.Also, just know that the bathroom leaves a bit to be desired. The shower curtain was moldy and the tub-to-shower switch didn't fully...

"Perfect stay for a quick trip to Portland! "

"Great home for family!"

"Incredible location right in downtown Freeport, and an even better host. We will definitely be staying with Jared again."

"Overall nice small place, owner responded quickly to issues. "

"If you are beach lovers this is the place for you. Pine Point is a dog friendly beach(look for rules and hours) and bike beach. Low tide offers hard packed sand. Great for running and walking!Lots of restaurants nearby and the cutest place just across the street, Salty Bay with a tavern only if you order food from Salty Bay so not a big bar scene just a few people and last call is 8:30! So perfect!It's great for a couple or a couple with young children. "