Family-friendly vacation rentals in South Portland

The house was perfect for our group of 12. It was spacious and well-cared for. While not located in downtown Portland, it was just minutes away by car. There was ample parking in the driveway and on the street. Meghan was a very responsive and flexible host. We had a great time.

Great location in town that was walkable to some terrific dining spots on main street. Enjoyed the backyard BBQ and patio for a lovely dinner outside as well as peaceful morning coffee. Sherry was very helpful in recommending the studio space for us and available throughout our stay. Will highly consider this spot for future vacations in Kennebunk area.

Meghan’s place was perfect for our family of four. A quick drive or bike to the beautiful beach; Woolf’s for fresh corn and pre-cooked lobster; Five Acre farm for freshly baked pies (love the honour pay system!). Also lots of amenities on the grounds to take advantage of (swimming, pool, tennis, pickle ball). Would happily stay at Meghan’s place again.

A nice private cottage in a quiet community that was super handy for us to stay until we secured our house in New England. Everything is in place for comfortable living. We lived there for a month long and the hosts were always responsible.

Nice stay, nice host, lots of recommendations in binder for things to do. Nice hot tub. Cozy place and location. DQ right across the street.

Jon’s cabin is a beautiful place to get away from it all. Very comfortable and well designed. We had everything we needed to cook and hole up for a few days. If you decide to drive to the lake, I would recommend 4WD. We had a truck but were not aware of how soft the ground was and ended up needing to be towed out. Still highly recommend! Enjoy your stay!

Dave was an amazing host and he provided the best possible get away for our first wedding anniversary. It was private there is so much beautiful outdoor art to look at and the hot tub was the perfect way to wind down after the day. If there was a 6 star option I would give it this was everything we wanted and needed and then some

Cottage was exactly as expected and perfect for our little family get away! The porch really added to the space and the cieling fans were very impressive. We loved the quite area and friendly neighbors. Would definitely stay again.

This was a perfect stay for our 2 days in Portland. We could walk everywhere from the apartment. There were plenty of options for restaurants nearby.

We arrived and saw either the hosts or prior renters had left a few key basic unopened items in the fridge to help ease us into our stay: items like half and half, some eggs and butter were present. The hosts had also made the effort to leave a small welcome and departing treat for me and the family that was a nice touch. The building was older but with that comes the charms of different features liked slightly raised floors at times and other anomalies. The rooms were freshly painted and we never saw any signs of pests inside.The location was close to the shore and walkable to the pier and attractions. The beach was extremely clean and though we only went at off hours (late night or sunrise) it was always relaxing. There is an active set of train tracks nearby so don't be alarmed, it's about a mile off I'd guess but you will hear them pass through.The roads were pretty quiet in the neighborhood and kids plays on the inactive street for hours. Thanks for the enjoyable stay, The Hornes

Marcia’s place was exactly what we needed for the week. Convenient location in town with several walkable dining options. So happy we chose Marcia’s place for our vacation.

Easy 5 stars! Phillip was kind, proactive and responsive. The space, while quaint and simple, was clean, had all the essentials and, it was perfect for a week visiting my grandparents/ working remote! Not to mention my dogs loved being a half mile from the Bath dog park. Highly recommend if you’re looking for a Maine mid-coast getaway!

Can’t say enough about how great our stay was! Andrew was incredibly responsive, let us check in early and check out late without even asking. It was a great location on the island, very walkable, even for my mother with a bad knee (she was exhausted after the first day though). Would absolutely stay again!! 10/10

Apartment was very good and has everything you need for your stay. Apartment was clean and easy access to downtown Portland with a 10 min walk. Joseph was very accessible we had a minor drain problem in bathroom and Joseph responded immediately and corrected the problem. Highly recommend this apartment for couples and small families. Would definitely rent in future. Thank you very much!!

This home was fabulous! The space was clean, lovely, and so comfortable. Additionally the neighborhood offered but walks in nature and restaurants/stores. I wish I could go back next month!

Super cute apartment in a great location and very responsive host! The apartment was clean and well stocked, and the Steve was very kind and responsive. He was also able to accommodate a very early check-in for us which was greatly appreciated. The location was great for getting around Portland. Our only complaint was that the free parking was not as easy/available as we had hoped, but the host did a great job compiling a list of other (paid) parking options. Overall loved it and highly recommend, just consider that you may have to pay for parking.

Our stay at the beach house was great! You couldn't be closer to the water! So much fun kayaking, floating and swimming in the lake! House is much better than the pictures do it justice. For a 2 bedroom house its very big and spacious, beds were extremely comfortable. The no wifi was a little bit of a downer but there were plenty of board games to play. There is some street noise but not bad at all. Would most definitely recommend if you are looking for waterfront property. The access to the resort pool was a plus too for the kiddos!

This place had everything we needed. The view was spectacular! We really enjoyed seeing fireworks from the deck. The home was very clean, kitchen fully stocked. We loved hearing live music each day and night. So much walkable fun for the kids. We had a wonderful stay!

Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones

Perfect little spot on Frye Island! Great location, walking distance to our favorite beach on island as well as the general store. House was clean, comfortable, just as described. We enjoyed our stay!

Maryann is SUCH a treasure! She really is the hostess with the mostest! Gives great recommendations, homemade coffee and treats, and if you mention you like something, she might get it for you! Making this Philly girl a wannabe Maine resident! Couldn’t recommend more.

Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown

My family and I had a awesome time enjoyed the quiet and relaxing days. Michael was very helpful and very quick responses to any questions we had.The cabin was very nice it felt like home was very comfortable slept very well. Everything about the cabin and the island was well worth going looking forward to going again in the future.

We had a great time at Teri’s place. The condo was described exactly, clean and had everything that we needed. The beds and furniture were. very comfortable. The view from the balcony was beautiful with nice chairs set out to enjoy your coffee. It was a 30 second walk to the beach, which was great for having a Toddler. The pool and laundry was a plus. When we head back to OOB we would stay again.