Family-friendly holiday rentals in Milwaukie

My Cozy Place- For the Budget Traveler-29 day max!

This cozy unit is a converted rec room located on the bottom floor of a two story house that includes a living room, a separate bedroom, a bathroom with shower, and a small kitchenette /laundry room (cold water). The kitchenette includes a microwave, toaster oven, hot plate, coffee pot, utensils, and refrigerator. The unit can be locked with key. STEPS are required for entry. Not recommended for guests with mobility issues. Extra guests are each charged $5 per day. NO smoking/vape inside.

Top of the World - Apartment near PDX w/ AC

This relaxing, private suite is perfect for your stay! Our organized space includes high-speed wifi, a gas fireplace, and even a washer and dryer. The kitchen is fully equipped with a dishwasher, fridge, Nespresso coffee maker, hot plate, cookware, and a three-in-one microwave/air fryer/mini baking oven. You have your own entrance and the space to yourself. Guests find the location very convenient and we often hear that the space feels comfortable, homey, and that we've "thought of everything!"

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.

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!

River Garden Cottage.

Charming cottage apartment on a garden and forest hill. Next to the Willamette River, 30 mins from downtown Portland. Relax, and enjoy the quiet and peaceful surroundings. Fully stocked kitchen. Fast wifi at 50 Mbps. Cozy inside in the wintertime, also with a park-like setting with walking access down the lush backyard to the river where you can enjoy swimming, fishing, kayaking, and bird watching. You can use the shared recreation room with ping pong, pool table, shuffleboard, and weights.

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.

Spacious and Private Place with a BIG Yard

Private and quiet space with over 800sq/ft of living space. Big living room and fully stocked kitchen. Relax in a queen sized bed next to an indoor fireplace. Kick back in the open concept space. Plenty of natural sunlight, separate key code entrance, and a big gated yard. 15 min to downtown Portland. Plenty of parking, close to the river and next door to a park which has tennis and basketball courts and is wonderful to walk and great for dogs. Can’t wait for your Portland

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

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 Sellwood District Studio

Welcome to our cozy studio located in the charming Sellwood-Moreland district - Perfect for the Portland aficionado who loves hand-crafted cocktails, eclectic shops, and live local music, making it the ideal location for those looking to experience the unique culture of Portland. The studio features a comfortable queen bed, full bath and kitchenette. The space is designed to be comfortable and inviting with quirky décor and plenty of natural light.

River Forest Guest House, River and Dock access

Tasteful and brand new guest house, beautiful neighborhood on the river. Guests have private deck facing yard and separate outdoor sitting area on the Willamette river (behind main house). Watch the birds, boats and riverboat cruise from the patio with fire pit. 2 miles from lightrail station, restaurants and shopping nearby and 15 mins. to downtown Portland. All are welcome! We are on the east side of the river, Milwaukie area.

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.