Family-friendly holiday rentals in Happy Valley

Woodstock Tiny House

Detached, very small (300 sq ft) guest house in the Southeast Portland neighborhood of Woodstock. Lots of walkable eateries as well as New Seasons and Safeway within a 5 minute walk. Close to Reed College, Woodstock Village, Springwater Trail, Southeast Portland Neighborhoods, Public Transportation. You’ll love the location, the outdoors space, and the ambiance. Good for couples, solo adventurers, and business travelers. TV (Netflix enabled!), A/C (summer months), heat, coffee, fridge/freezer.

1000+ sq private 2b1.5b unit in gated area

A private unit in gated resort like homesite centrally located. Kaiser hospital , Clackmas TC and Happy Valley TC are mins drive away. 25 mins to PDX, NW 23rd ave, Portland downtown and 50 mins to Mt Hood. Very quite and you can wake up to bird chirping in am. Evergreens provide nice soothing color year round. Patio and deck with dinning table give you chance to enjoy outdoor and sunset if weather permits. Full kitchen. Up to 1gb super fastinternet. Spacious for 4 no extra charges. Central a/c.

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).

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

Mid Century Villa w/Mountain View & Movie Theater

Just relisted as we had long-term renters due to total fire loss. 3400 sq ft hillside retreat decked out with rare furnishings. Take in the Cascade Mountains from the wraparound deck and lounge under giant maple trees. You'll love the 125” Hi-Def movie theater (w/ 200+ movies)! Two large primary suites with king bed and large showers. One additional queen bedroom and one large office. Close to urban and nature, 20min to the airport, with daytrip opportunities to all the PNW must-see spots.

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.

All the Views: Your Private Getaway Near Portland!

Guests tell us they love the view! They also mention this downstairs apartment is very clean, spacious, comfortable and relaxing, with great wifi too! • 750 square feet of privacy, including a large private 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. Garage entry. Level 2 EV charger Clackamas County License #108

Light Filled Garden Studio

Our wonderfully bright garden studio is perfect for a short stay or for visitors looking to explore Portland for an extended visit. It has a full, well-stocked kitchen, ideal for those looking to stay in and cook, but it’s also just a 20 minute drive from downtown, for those looking to explore the wonderful restaurant scene Portland offers. Keyless entry and private entrance through the side yard gate provide renters with complete autonomy during their visit.

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.

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. You must be in physically good shape to handle this location. We have friendly dogs you may see outside, and we do not allow pets. SE Portland is a 30 min drive and downtown Portland a 45 min drive. One hour to Mt. Hood, 40 min to waterfalls in the Columbia Gorge. Pool open June 15 through September 5th.

Milwaukie Retreat in the Woods

Your private apartment is located on a wood filled lot with a private outdoor area, shade and even deer on occasion. We are 12 miles from the airport, near freeways with easy access to downtown, and to make your way to the coast or the Columbia Gorge, Mt Hood and the Willamette Valley for wine tasting. We have added extra cleaning procedures to help fight against Covid 19.

Modern Townhouse

Newly built gated Modern Townhouse. Beautiful and scenic drive to Timberline Lodge / Mt. Hood Ski Bowl. 25 minute drive to downtown Portland. 15 minute drive to Clackamas Town Center. Minutes away from 172nd / Sunnyside shopping center and restsurants. Close drive to Multnomah Falls. Close drive to Vista House view point. Lots of hikes and trails nearby.