Family-friendly vacation rentals in Happy Valley

Secluded Studio

This a fully private and detached guest house is quiet and relaxing. Walk down your very own pathway to a completely private, safe and secure patio with a quaint garden, a small yard and outdoor seating. With tall ceilings and a large nice bright kitchen, this place is very comfortable. Blackout curtains. Close to many desirables: Max Orange Line Commuter Train, Reed College, Woodstock, Sellwood, & East Moreland & Milwaukie Providence Hospital. Ride, walk or run along the Springwater Corridor.

Indoor spaces · Kitchen · Long stay

RoofTop FirePit, HotTub & Outdoor Theater

Our large (1,500sq ft) space (private access), has a bedroom, bathroom, living room w/ a fireplace, hot tub, full gym as well as a kitchenette w/ full sized fridge, keurig, microwave, air fryer, toaster oven, single burner, and laundry facility. Smart tvs, hammocks and a rooftop firepit are in the outdoor entertainment area. LGBT & BIPOC friendly. Gym, hot tub and laundry are shared with owners but guests have priority access. Close to Mt Hood Wilderness (45mins) & Downtown Portland (15mins).

Family · Indoor spaces · Outdoor spaces

Luxurious Riverfront GuestHouse, Sauna & HotTub.

Welcome to our Clackamas Riverfront Guest House—a peaceful riverside retreat blending rustic charm and modern comfort. Relax in your private hot tub and sauna, unwind by the fireplace, and enjoy stunning river views. Fish, kayak, or raft right from the backyard. Bedrooms include white noise machines and earplugs to help with normal traffic during commute hours on our scenic road. The guesthouse is attached but its own private unit with its own separate entrance and parking. Enjoy your stay!!

Indoor spaces · Family · Condition

Peaceful Spacious Single Level Home

Look no further if you are looking for a clean & spacious home with all the amenities for a comfortable stay. Single level with a walk in ADA shower in the primary bathroom. Dedicated office/den with excellent wifi. Remote work & family friendly. 5 minutes away from the Clackamas mall, Costco warehouse/gas, Target, REI, restaurants, Kaiser hospital. Clackamas is a suburb of Portland, only 25 min. drive of downtown and airport. *Co-hosts conveniently live nearby to assist whenever needed

Kitchen · Family · Backyard

All the Views: A Private Airbnb Near to Portland!

Guests tell us they love this view! They also mention this downstairs apartment is very clean, spacious, comfortable and relaxing, and has great wifi. • 750 square feet of privacy, including a large guest-only deck • Full kitchen, queen size bed and fast wifi • Leather furniture, large screen TV with HDMI capability (streaming only) • Private staircase leads to your garage entrance. No shared spaces. Level 2 EV charger Clackamas County License #108 No children or infants, sorry.

Kitchen · Family · Comfort

The River’s Bend

Bright & airy ADU right on the great Willamette river! Complete with kitchenette and private entrance! Walking distance to the public transport train (max station), Elk Rock Island State Park, downtown Milwaukie, and only 10 minutes by car to downtown Portland. The riverfront park green space and boat launch are quite literally steps away from our front door. Take a walk along the beautiful river! *Note: there is a single-story flight of stairs leading up to the ADU on the second floor.

Kitchen · Indoor spaces · TV

Hygge House-luxurious secluded 3BR guesthouse

The Hygge House PNW is a place to unwind, get cozy and enjoy the company of those you love. Cuddle up with a cup of tea or a good book and enjoy a restful retreat. Enjoy country vibes while being moments away from Happy Valley City Center. Whether you're in town visiting friends and family or looking to experience everything Portland has to offer, the Hygge House has you covered. We hope you enjoy your time spent here and leave feeling relaxed and more connected with the ones you love.

Indoor spaces · Family · Parking

Quaint Tiny House In The Trees. Damascus, Oregon.

150 ft. walk down a steep driveway takes you to a unique private little studio with everything an adventurous spirit needs. We have friendly dogs you may see outside, and we do not allow pets. No smoking in the unit. There is a smoking hut on the property you are free to use should you choose to (bring a container with you to dispose the remnants). SE Portland is a 30 min drive and downtown Portland a 45 min drive. One hour to Mt. Hood, & falls in the Gorge. Pool open 6/15 through 9/5.

Kitchen · Family · Quiet

Happy Valley - Serenity in the Suburbs

We offer you a spacious (1500 sq feet with 9 ft ceilings) daylight apartment which includes, 2 large bedrooms (one queen, two twins), full kitchen with basic supplies, full laundry, bathroom with shower, dining and living areas, office nook, covered outdoor patio for sitting, a secluded and quiet backyard great for birding, private parking spot and separate entry. Our property backs up to a protected nature area with a beautiful walking trail. Perfect for couples or a small family.

Kitchen · Family · Walkability

Modern Spacious Private Guesthouse!

This spacious guesthouse is the perfect spot to relax and unwind, located conveniently just a few minutes from an abundance of restaurants and stores. The home is equipped with a queen bed and futon, kitchenette, and dining area. For your convenience, you have your own washer and dryer in the unit. Explore stunning Oregon beauty by adventuring to the nearby parks and trails. If you'd rather cozy up inside, the guesthouse has free-wifi and Netflix.

Indoor spaces · Kitchen · Parking

Breathtaking views, Fish, Ski, Mt. Bike, or Hike

Experience a charming two-bedroom suite in the daylight basement of a two-story home, complete with a private entrance and covered patio. Enjoy breathtaking views of Mt. Hood and the Sandy River from your beautiful backyard. Nestled near Oxbow Park, you're just minutes from shops, restaurants, and outdoor adventures in the Columbia River Gorge and beyond. With the Portland airport only 25 minutes away, this cozy retreat is the perfect getaway!

Kitchen · Family · Laundry

Foxglove Farm Private Guest Suite

Enjoy a stay in a ground level suite in our two acre country home. Experience the privacy and quiet of the countryside, yet shopping and restaurants are just moments away. We are 30 minutes from PDX and downtown Portland, less than an hour from Mt. Hood and the beautiful Columbia River Gorge, and 90 minutes from the Oregon Coast. You will have your own private entrance, and have access to a porch and deck with scenic views.

Kitchen · Indoor spaces · Long stay