Family-friendly holiday rentals in Oak Grove

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.

It’s more comfortable and more beautiful than all the pictures. The river is completely visible from the living room and you can hear it all night. Within a 20 minute drive you can find amazing spots for hiking, swimming, scenic views, a few local restaurants(Pacific Northwest Pizza is amazing!), and just about anything else you would want from a location like this. If you’re willing to go an hour or two away you can get to Mt. St. Helens, the Gifford Pinchot National Forest, the Columbia River Gorge, and plenty more. The only hiccup we had for our stay was when we accidentally locked ourselves out and the Wi-Fi happened to be down(the provider’s issue, not our wonderful hosts’!). Thankfully someone was at the other house on the property to help us. The hosts were always very friendly and respectful of our privacy. We loved our time here so much and would recommend it to anyone looking for a beautiful, peaceful, and fun place to get away. We hope to come back some day!

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

Our stay was incredible! Rachel And Rico perfectly described their lovely home, and even then, it was more thanwhat we could have thought. Perfectly located near Sandy, we couldn't have asked for a better place to stay. Relaxing in the hot tub and hearing the river near the property was very relaxing. Rachel And Rico were incredibly helpful and responsive, and even checked on us during our stay. When I one day come back to Oregon again, I will definitely stay here again.

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.

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

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.

The Hen House was perfect! Beds were great; we slept comfortably every night. Super cute house, great neighborhood, and the cats were the sweetest welcome team! Thank you for letting us stay. We will be back!

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.

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!

This was an amazing treehouse! The property is super awesome, peaceful, beautiful, incredibly relaxing! They were such sweet hosts as it was our anniversary and we came from a perimeter walk to a nice surprise! Very thoughtful host! I highly recommend staying here! Thank you both!! 😊