Family-friendly holiday rentals in Milwaukie

All the rave reviews were accurate! We had a great time and the same has everything you might need. Immediate relaxation!

The Little House was peaceful & quiet, with a nice private yard for me & my dogs! Chris was helpful and friendly, I would recommend his place to anyone!

Gem of SE is right. Walkable to coffee shops and all of Hawthorne without being in the hussle. Air conditioning during a Portland summer, oh ya, theve got it! Very peaceful backyard. Felt secluded in the hot tub. This place is great! The shower is missing a door but other than that, everything was amazing.

I had a fabulous stay at Therese’s place! It was incredibly peaceful and calm, with stunning views of the river right from the bedroom — such a perfect way to start the day. Therese was so friendly and kind, and as it was my first time visiting Portland, she went above and beyond by recommending lots of great things to do and see. She even brought us our favorite breakfast items to enjoy— such a thoughtful touch! I would definitely stay here again anytime I visit Portland. Highly recommend!

This little studio is so cute and the view from the patio is beautiful.

An absolute gem of a place to stay. Do not hesitate to book. Beautifully designed. Wonderful wolf gas rage in a state full of electric stoves. A wonderful place to stay with friends, we didn’t want to leave. We will be back. Bigger than I expected from the photos. Thank you for a wonderful stay!

Melissa was the best host I have ever had! She went out of her way to accommodate me and my kids. We landed late and she proactively offered to set up the futon bed for us and even left us some food. We enjoyed our stay. The yard was great. Great walkable location. We would definitely stay here again when in Portland.

It is very peaceful and beautiful. The hot tub on the deck adds a feeling of luxury. The internal stairs are quite narrow but manageable (we went up and down these all the time), and if you are not limber you should take the external stairs that are nice and wide. VERY comfortable bed. Overall highly recommend and will likely come back

We stayed here long-term while house-hunting and had the most amazing time. This space felt like home, the hosts were kind and very welcoming, and the neighborhood was a dream. Very walkable and historic. This ended up being our new favorite neighborhood in Portland! Thank you James for the most perfect stay. Highly recommended!

Exactly what we needed. This spot is in a very quiet, beautiful neighborhood. 10/10

Nathan and Liz are amazing hosts! They clearly take a lot of pride in their Airbnb, and the loft was very clean and well laid out. I would definitely stay again during my next trip to Portland!

Great stay! Very peaceful! Wish I didn’t get so sick- because we would have enjoyed more of the area! Chill spot!

This was my second stay with Andrea and it didn’t disappoint. Cozy and calm retreat within walking distance of all the Mississippi fun. Loved having morning coffee with my dog on the outdoor patio space. This is earmarked on my Portland list for my future trips.

For the price I paid, I am extremely happy with my experience. The space was clean and very close to the airport. Shane is very attentive and communicative; I never felt like I was being ignored or that he had other priorities. I'd recommend this place to any solo/duo travelers looking for shelter close to the airport. Some very minor gripes (me being very picky): -The overhead shower was great, but I wasn't a huge fan of the protruding stones on the floor - I have bit of a sensitive nose and all I could smell when entering was laundry detergent fragrance (which at least means things are clean) - Finding space for parking was no problem at all, but it is on a slope, which coupled with having to cross the road might be difficult for some elder travelers or those with disabilities

I’ve stayed at several airbnbs over the years and this was my favorite! We wanted for nothing. It’s a great, tucked-away location within walking distance of amazing coffee and restaurants. I’d recommend to anyone interested in visiting Portland!

This is our 5th time staying at Susannah's! We always look forward to coming 'home' when we get to Portland.

Our magical vintage trailer getaway was pure cozy bliss! Tucked away in a charming little spot, the rain only made the weekend feel more enchanting. With our pups snuggled beside us, we spent the days playing board games, sipping warm drinks, and listening to the soothing patter of raindrops on the roof. The trailer’s retro charm added to the whimsy, making it feel like we had stepped into a dreamy little hideaway. It was the perfect mix of nostalgia, relaxation, and fun—proof that sometimes, the best adventures happen indoors.

Awesome trailer. We checked in afterhours and they were very accomodating and nice. Great location. Truly enjoyed the experience

The trailers were fantastic! Some friends and I stayed as a last minute weekend get away and we could not have asked for a better time. I can't wait to come back. Wineries are close by, and the scenery is beautiful. Highly recommend!

Very clean and well kept space! Would definitely stay again, we loved it. Bridget was very kind and responsive as well!

The trailer was great. What an awesome idea! It was so nice being right in the middle of wine country and being able to drive down the road. The extra accoutrama like the pour over coffee and space heater made this better than it needed to be. Would definitely do this place again, thanks!

This is the second time we've stayed at Shelley's place and it was just as good the second time around. While there are a lot of posted rules and guidelines around the house, they have obviously helped keep her home immaculate for guests. She communicates incredibly well and is more than accommodating to any special needs or requests. She invited my group to come up a night early due to her previous renters checking out early and offered us a check-out at any time of the day, not rushing us out at all. The pool and view are unmatched and I highly recommend this location to others. If we're in need of a rental in Sherwood again, Shelley's place will be our first choice.

Julie was a generous host. It was a peaceful place for my family to stay and easy for our local family to come for meals and visit. Every morning we had coffee on the large private deck. We sat on the deck some evenings and enjoyed the fresh air and complete lack of mosquitoes. The two full bathrooms for the five of us were essential. We booked this house to have a great place to stay-in and have local family over but it was also close to many things in Portland. The zoo and the science museum were two of them. Julie was responsive to requests and just a very kind person.

Wonderfully fun to stay in a time capsule! I was so impressed with how clean and well kept the trailers were. Felt like mint condition!