House holiday rentals in Milwaukie

Mama J's

For whatever brings you through/to Oregon, stay at Mama J’s comfortable, peaceful, safe and convenient spot. Portland is just ten miles away, the closest beaches, Columbia River Gorge and Mt. Hood are all about an hour, and there are numerous hikes from the forest right down the street to Silver Falls and beyond. The neighborhood is peaceful and your private patio is the perfect place for a beverage and some bird and squirrel watching. If it rains, hang out in the gazebo! Hope to host you here!

Portland Modern

Welcome to our Midcentury Modern – a true masterpiece inspired by the iconic Frank Lloyd Wright. Nestled on a lush 1/3 acre private retreat, this architectural gem is just minutes away from Multnomah Village and Gabriel Park. Immerse yourself in the timeless beauty of this completely renovated mid-mod marvel, where high vaulted open beamed wood ceilings adorn every room on the main floor. This house is perfect for friend groups, families or corporate retreats. Note: 4 bedroom, 2 bath, 2 kitchen.

Springwater Retreat: Relax in quiet comfort

In a tucked-away corner of Portland’s closest suburb, you will find our private duplex on a large, private park-like lot. We are located 8 blocks from the Springwater Corridor, a popular biking/walking trail on the Portland border. It is a lovingly furnished home: queen bedroom, twin-over-full bunk bedroom, bonus room that has a very comfortable queen sofa bed and foozball table, fully equipped kitchen for real cooking, dining area, and huge private yard. Only the off-street parking is shared.

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).

Forested Hygge House Getaway

Relax in a Gladstone oasis overlooking an untouched trail and forested area. A cozy, bright, and private spot. I hope you connect with my affinity for vintage art and clean lines! You’ll have the entire house and 1/3 acre to yourself. Less than 30 mins from most anywhere in Portland Metro, 10 mins to Oregon City, and 1 hr to Mt. Hood. This is a dog friendly (no cats), non-smoking house. The large yard is on a dead-end street, though not fenced. *Not ideal for those with mobility issues*

The Clinton Modern

The Clinton Modern is a clean and contemporary accommodation located in the heart of the famed Clinton/Division neighborhood in Portland, OR. The neighborhood is itself embedded in the equally renown East Portland district, known for its dynamic food, rich cultural offerings, and quirky nightlife. The locale is quiet yet conveniently accessible to all this great city has to offer. If you're looking for a space to both adventure from and return to congregate with friends, look no further!

Crossroads Country Cottage

Conveniently located at the crossroads of HWY 224 and SE Lake Road, our home, cottage and garden are the last remnants of a time gone by and what was once a large family farm. When you walk through the private gate leading to the cottage, you might feel you have stepped through a portal into another time. Everything about the cottage is secluded, peaceful and private. We are pleased to have many return visitors. The garden features a waterfall, chairs and table, BBQ and fresh herbs.

#StayinMyDistrict Sellwood Coco Rose Retreat

#StayinMyDistrict Sellwood Retreat! This private garden Retreat is located in the heart of Sellwood! Live like a local and experience a vibrant SE Portland neighborhood! Known for its “walkability” and “friendly neighborhood feel”! Walk (1 block) to local hotspots, nightlife, dining, coffee, & boutique shops, from this comfortably appointed Queen Studio Suite. Relax and enjoy a glass of wine on the private patio. Kitchenette & kitchen amenities, W/D in unit, FREE street parking!

Oak Grove Easy-Centrally located w/King Bed

Welcome to this updated and comfortable, light filled home in the Oak Grove neighborhood of Portland. A short distance to the river, downtown, parks, restaurants and all things Portland-make this a perfect vacation space for your family and guests. We put a lot of love in to designing the interior to be stylish, yet comfortable and seamless to ensure you feel right at home. Ample space in our park-like backyard to relax , entertain or play a summer game of corn hole!

Multnomah Village Hideout

Explore our new, artist-built bungalow in Multnomah Village, Portland. This cozy space sleeps four with a queen bed upstairs and a pullout couch downstairs. Steps away are charming cafes, shops, and a park with hiking trails and dog parks. Enjoy local activities like bingo and dining on pet-friendly patios. Complete with essentials including laundry and a breakfast nook, this bungalow is perfect for both short and extended stays, offering a unique Portland experience.

Newer Built Fopo Gem, Close to Everything!

Our newly built bright and modern guest house is fully equipped with all the modern amenities you need to relax and recharge after a day of adventuring in the city. It is located in the popular FoPo (Foster-Powell) district and is the perfect location for exploring Portland. Heaps of local coffee shops, bakeries, food carts, bars and breweries are just minutes of walks away. Also easy access to local parks, shopping districts. We would love to host you!

Cozy Creekside Farm House Renovated on 1/3 Acre

We have power! Private farm house on 1/3 acre with creek running through the yard. Vegetation surrounds you and neighbors are limited. Fully renovated house with new floors/plumbing/electrical. 3 cable televisions with high speed internet! Close to the Spring Water Corridor Trail for walks/runs/bike-rides. 5 minutes from Woodstock 15 minutes from downtown 20 minutes to airport Close to Cartlandia, Portland's original food carts. $30 per pet.