Family-friendly holiday rentals in Milwaukie

Dream Cottage! Springwater Bike/Walking Path!

Explore, recharge, dream in your own quiet & inspiring country-in-the-city cottage. Sellwood is a great riverside neighborhood, featured in Sunset’s Best Places to Live in the West. Set off on a bike path adventure or start your novel at the writer’s desk. Walk to coffee shops, restaurants & New Seasons Market grocery. Ideal for College visits: drive times, 10 min to Reed, 10 min to Lewis & Clark, 15 min to PSU. Note: PLEASE ASK about weekly or monthly discounts if you're planning extended stay!

River Forest Lake Apt w/hot tub. HOT find!

*No smoking, no parties, no drugs or pets on premises* total/Max 4 guests; included in this total are infants/children, no more than 2 or3 children under 12, as long as only 4 total guests. FYI: Incline driveway Welcome to our newly remodeled daylight basement apartment. Tucked into the quiet peaceful River Forest neighborhood of Milwaukie on River Forest Lake. Conveniently located to shopping, restaurants, hwy 99, freeways to Portland, Oregon City, historic Sellwood, the Gorge, Mt Hood, etc.

Clean & Cozy "Private" Studio Suite

Private studio suite (500 sq ft). The unit is on the lower half of this 2 level duplex (host lives upstairs), private entry is on the ground level, self check-in, off street parking. There is a kitchenette, private bathroom with a stand-up shower, washer & dryer, queen bed, high speed internet, expanded cable, Netflix/Amazon Prime. Also, there is a lovely private patio for your enjoyment with a fire table. The space is warm and inviting, very safe location, great neighborhood and dog friendly.

Upstairs Rustic 1940s styled Studio Apartment

Great for water loving people! Private unit. Self checkin. Outdoor patio & yard. Wifi. Pet/animal free, allergy safe. Smoke free. Linens washed with Defunkify perfume free soap. Fully stocked kitchenette. .75 Bathroom (sink, toilet, large shower) Stocked w/ toiletries. AC in summer. Complimentary snacks! 1940's vintage furniture. Quiet neighborhood. Semi-industrial parking, as we run a pressure washing biz. Your unit is around the back on the 2nd floor. 1/4 mi to bus route at top of hill.

Spacious Studio near Historic Milwaukie/Sellwood

No cleaning fees! Unique retro inspired LARGE studio Private entrance, driveway parking. One Full sized bed and a comfy twin sized cot (set up upon request). Bright sunny space with skylights and beautiful details. Uncluttered, quiet and clean. Full sized fridge and plenty of kitchen amenities. Large dining room table and sitting space. Located in peaceful neighborhood, close to Historic Downtown Milwaukie, 15 min to downtown Portland, minutes away from SE Portland attractions!

The Room In Between

Private and secure entrance to this modern and 5-Star space! Comfortable Queen Murphy bed that converts to a sofa. Fast Wifi and Smart TV w/access to Netflix & Prime Video. Fenced yard with security gate entrance, off of private paved driveway, to lead you to your own private patio & room entrance. Self check-in is at 2pm or later. Check out is 11am. No pets. Smoking allowed on the outside patio only. Flat entrance pathway is well lit from your parking space to your room & patio.

SE Portland Guest Cottage

The guest cottage offers self check-in. It is located in a quiet neighborhood in SE Portland. High ceilings make this studio airy and bright. We think of it as a perfect hotel room without the hotel. The small galley kitchen has everything you need to cook a gourmet meal including filtered water. There is a full bathroom with tub and shower. The cottage stands on its own making it perfect for coming and going as you please. City of Portland Permit #24 013532

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.

Lovely 1-bed vacation home w/ off street parking.

Welcome to the artists nook - where characters and wayfinders come to relax. A stylish, freshly remodeled 1bed, 1bath, in a quiet, serene neighborhood. 1 Private off street park space. Private Back porch with bbq. Every room has heat keeping it nice and toasty on those cold, winter nights and AC for July's sultry, sticky evenings. Kitchen comes fully equipped. Large bathroom, and don't forget to use the huge washer and dryer to get your laundry in check.

Rustic Creekside Cabin

This tranquil hideaway feels like you're in the middle of the forest, but is just minutes from Portland. Relax next to the burbling creek surrounded by towering cedar trees. The MAX Orange line and downtown Milwaukie are only five minutes away. Built in 1928, the cabin has one bedroom and bathroom, living room, full kitchen and central heat. The bedroom has one queen bed and an en suite bathroom. There is a pull-out queen futon in the living room.

Cozy, Private Studio

This beautifully remodeled studio with private bathroom, entrance and off-street parking is nestled in a quiet, relaxed neighborhood in Milwaukie- a neighborhood south of Portland. Extremely comfortable queen bed will provide you with an excellent nights sleep. Great atmosphere for those traveling for business or vacation. Located 5 minutes from I-205 and a 10-minute drive to downtown Portland.

Sellwood Detached Studio Loft

Self contained cozy yet bright studio apt located above our garage in the heart of charming Sellwood! Though no interaction is required, hosts are close-by and available as needed! Steps away from shops, restaurants, coffee, bars, parks, trails, and the river. Within a few miles of both Reed and Lewis and Clark Colleges. You will have all the privacy you need in this detached unit! Sleeps 2-4.