Family-friendly holiday rentals in Westport Island

Lori’s is exactly what we need while visiting family over a holiday. She is very gracious to host us over Thanksgiving as the last occupants of the year. Even during a snow storm, her place is cosy and beautiful. This is our second year coming, and we love it every time. We would recommend it for those looking for a charming getaway from busy life. Thanks Lori!

We really enjoyed our stay at Woolwich. There is a peaceful nature vibe to the house and a beautiful view and location. The Bald Eagles live in a tree right on the edge of the backyard and were visible numerous times during our stay. The location to various towns and locations in Maine is convenient.

Meghan's home was a perfect place to stay for my sister's Bachelorette weekend! The home is located in a quiet community with views of the river and bay, and it was conveniently located with just a short drive into the heart of Portland. We found our stay extremely comfortable, especially on such a cold and dreary April weekend. Meghan had the hottub ready for us with matching robes for all which was a fun surprise. Check in and check out were a breeze. We even took a breakfast recommendation from the guest book (Forage Market, yum!), a tasty experience indeed. Thanks again, Meghan!

We had the most amazing stay at Madawaska! Amazing views from the bedroom and hot tub in a beautiful, peaceful, and private location overlooking the water. And such a wonderful design of the cabin. We will definitely be back!

Just returned from the most fantastic 2 weeks exploring the US which included a weeks stay at Kiwi Lodge. Where to start? This was exactly as described and the perfect base for exploring Maine. The property was spotless and has all the amenities needed for a comfortable stay. 3 beautiful bedrooms, 2 great sized bathrooms, wonderful living area and kitchen and fantastic games room. Hot tub was brilliant. The location on the lake is just perfect, we had the lake to ourselves and took the canoe out. Nearest town of Farmington has all the shops and cafes you’d need. The communication from Kay was great from the day we booked, and recommendations we took her up on were all absolutely spot on. Thank you Kay and thank you Kiwi Lodge for a holiday to remember!

This house has a beautiful location super close to the beach and a close walk to restaurants and activities. It has great views and plenty of room for a large group! Check in was super easy and they greeted us and went through everything so clearly that we knew where everything was and how to use it all - which was very helpful with such a big place with so many amenities. The hosts were communicative and helpful leading up to our stay and again with check out. The house itself is stunning with everything stocked for your stay. The only thing to be aware of is that there is a train that runs close by so definitely bring your sound machine. Would definitely rent this place again!

Great place. The bed was really comfortable. Hot tub was nice and private and relaxing.

Beautiful home with a great view, deer and turkeys in the front yard. Very quiet and peaceful. The home is well equipped and spacious.

First off. Let me say the house was great. It was nice and big plenty of room. Very clean we had a big gathering and everyone absolutely loved it and was very satisfied with the price they paid to stay the weekend. Even though we went during the offseason it was still a great time. We Will definetly book this Airbnb again. Thank you Krystal and we will be in contact again.

Cozy and comfortable place to stay while exploring the area. Close to most anything you’d want to do in Southern Maine.

I loved this place! Enjoying coffee and meals outside on the deck overlooking the lake and beautiful surroundings of nature. I felt safe there and was a charming neighborhood. I loved that there were boats to use and a dock to watch sunset an autumn harvest moon over lake! Jess was the perfect host and made sure everything was great when I arrived. She was very helpful when I had any questions and I am looking so forward to going back there again! Thank you Jess for sharing this wonderful place!!!

Sadie and Laughlin are the best Airbnb hosts we have come across. We could not have asked for a better place to stay. The apartment is very clean, has lovely furnishings, is nicely decorated and had everything we needed for a very comfortable 3 and a half day stay in Portland. Both bedrooms are a good size and have incredibly comfortable beds. When we needed help with something, our hosts came around fast to help us. If we are ever back in Portland, we shall gladly book again with them. I would highly recommend this apartment!

We absolutely loved our stay! We rented the house for 7 adults and 1 dog to celebrate a 31st bday! We loved being able to walk right down to the tasting room for a beer, cook a big dinner in the kitchen, play games, and watch the amazing vcr collection. Everything was clean and comfortable. So glad it’s a dog friendly space!

We loved our stay at Katie's house in Portland. It was very comfortable, clean and nicely decorated. We would love to stay again soon!

A group of 5 of us stayed at Kathy's listing and felt like we had plenty of room. We were all comfortable and found the location to be great with plenty to do within walking distance. Some of the doors were glass with blinds/shades that weren't entirely opaque so we had to be somewhat mindful when changing in our room. The front door battery was dead when we arrived and so the door was unlocked but this was quickly resolved with the help of the host and extra batteries on site. Location was fabulous and peaceful. No issues with finding free street parking, either. Overall, we enjoyed our time here and would stay at this listing again!

Great retreat to feel relaxed and inspired. The location suits our needs for comfort and accessibility to surrounding disc golf courses and is great for travelers looking to escape screens, and the stress of cluttered and busy lifestyles. It feels like home as soon as you arrive .

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!

Alice’s condo in Old Orchard Beach is exactly as advertised. It was in sparkling condition when we arrived, it’s a very short walk to the beach (when we were able to tear the kids away from the pool!), and it is the perfect distance from the center of town: close enough to walk, but far enough away to enjoy some privacy and distance from the crowds. We even managed to squeeze in a quick workout in the small gym. We would absolutely stay here again. Thank you so much, Alice!

Our stay here was amazing, the house is adorable and the views are stunning. The pool was the perfect temperature and the whole family was in the pool every day, plus the views from the pool were pretty remarkable. Sherri was a great host and super communicative and helpful. The house is set up perfectly for a large group with cute little restaurants a short car ride or boat ride away. We will definitely be back!

Maryann was friendly, responsive and quick to reply. She left baked goods and coffee out each morning which was a pleasant surprise. The space was easily accessible, private and spotless. We would definitely stay here again

Great place to enjoy the beach and the neighborhood 😃

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

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.