Family-friendly holiday rentals in Portland Downtown

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.

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

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.

We were in Portland for our son’s graduation and Arlene’s place was one of the best we’ve stayed at. The garden was peaceful and magical, the home spotless and well-equipped. Arlene was super responsive and even helped with our laundry. Highly recommend!

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 had a truly wonderful stay! The space was incredibly clean, peaceful, and beautifully decorated—with thoughtful touches throughout that made it feel extra special. It was private and quiet, yet perfectly located for exploring the Portland area. Parking was easy, and the neighborhood felt safe and welcoming. The hosts were extremely kind and communicative—we felt well taken care of from start to finish. We were very impressed and would absolutely stay here again!

Adorable little adu. Beautifully designed and impeccably clean. I had a lovely stay. And it was so fun to see the chickens!

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

My friend and I had such a lovely stay! The loft has beautiful large windows letting lots of light in as well as curtain that could block the light to keep the place cool. Both the bed and the futon were quite comfortable with nice quality linens. The place was quiet, peaceful and clean and both of us felt right at home. We ran into the host (and their adorable pups) coming out of the loft. They were kind and asked if we needed anything. Such gracious friendly people! Overall it was a great stay! Will be booking again in the future! Thank you so much!

We had a lovely stay at Stephen’s place! Hidden away behind the main house, the place felt secluded and private. It was equipped with everything we needed to cook, and stocked with thoughtful toiletries. Close to all the main grocery stores, and walking distance to Hollywood Theater. I highly recommend staying here!

Jacob’s place is as advertised and was great. The neighborhood is a classic Portland residential district and about a 4 minute drive from the cool, quirky venues in St Johns. Jacob is personable, and his place is quiet and very comfortable. I look forward to staying again as I’m a frequent visitor of Portland and Jacob’s is among the best places I’ve stayed.

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!

The apartment was spacious and well equipped. A meal could easily be prepared in the large kitchen, laundry done, and even ironed. Zanna was very responsive when I mentioned that certain products were running low. Also very nice to have the use of a private patio with table and chairs. I will stay here again if I plan to be in Portland for several days.

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

Tessa was so great to work with. We got in pretty late and she had the lights on for us and gave very clear instructions on how to find the place and where to park. It was clean & cozy!

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.

This is the second time my elderly dad stayed here and he loves it very much. He considers it his “Portland getaway” now. It’s just right for him in every way—so nicely decorated, accessible, homey. He loves that he can walk on his own to get coffee down the street and not get lost. And Andy and Gina are wonderful hosts. My dad has already said he can’t wait to come back again!

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.

This home well exceeded my expectations and the photos truly don’t do a justice to how beautiful everything truly is. The views were incredible and the house itself is extraordinary, plenty of space for guests to have room to roam, the amenities are to die for and overall I have been blown away! My only regret is not booking for longer. The host was very informative and kind throughout the entire process.