Family-friendly holiday rentals in Milwaukie

A detached guest house is highlighted, featuring a blue exterior with large windows and a front door. A small patio area with a wooden table is visible, surrounded by lush greenery and decorative plants. A wooden fence provides additional privacy.

4.95 out of 5 average rating, 125 reviews

Secluded Studio

This a fully private and detached guest house is quiet and relaxing. Walk down your a private pathway to a completely fenced, 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 Commute Train, Reed College, Woodstock, Sellwood, & East Moreland & Milwaukie Providence Hospital. Ride, walk, run or ride along Springwater Corridor.

Indoor spacesFamilyLong stay

A serene entrance features a wooden archway draped with greenery, leading to a tranquil lake. The lush yard is complemented by a carved bear statue, and mature trees provide shade. The calm water reflects the surrounding greenery, creating a peaceful atmosphere.

4.95 out of 5 average rating, 461 reviews

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.

KitchenIndoor spacesDecor

4.93 out of 5 average rating, 187 reviews

The kitchen features a retro blue fridge and dark cabinetry, providing a blend of modern and vintage aesthetics. Natural light enters through a window above the sink, illuminating the space. Indoor plants are placed around the room, enhancing the overall atmosphere.

Guesthouse in Milwaukie

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!

KitchenIndoor spacesSleep quality

A serene garden scene captures early morning fog enveloping vibrant fall foliage. Lush greenery is interspersed with colorful autumn leaves, providing a peaceful backdrop. The landscape features a variety of shrubs and trees, adding depth and texture to the tranquil environment.

4.95 out of 5 average rating, 195 reviews

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.

FamilyKitchenCheckout

The exterior of the ADU features a modern design with a combination of wood and stone materials. Large windows allow natural light, while a covered entrance provides shelter. The entry door displays a contemporary style, contributing to the overall aesthetic of the building.

4.9 out of 5 average rating, 108 reviews

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.

KitchenIndoor spacesHospitality

An open and airy living area features a light-colored sectional sofa with a navy throw, centered on a patterned area rug. A coffee table sits in front, and a television is positioned nearby. The space is complemented by dining and kitchen areas in the background.

4.95 out of 5 average rating, 109 reviews

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 BRAND NEW 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

Indoor spacesKitchenCleanliness

A warm dining area is showcased with a wooden table at its center, surrounded by decorative plants. An archway leads into a cozy living room featuring a gas fireplace, comfortable seating, and large windows that invite natural light into the space.

4.97 out of 5 average rating, 135 reviews

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!

KitchenFamilyHeating

4.89 out of 5 average rating, 770 reviews

The cabin, nestled among towering cedar trees, features a rustic exterior with warm lighting from the windows. A serene creek flows nearby, with smooth stones and mossy patches lining the water's edge. A wooden bridge connects to the surrounding natural landscape.

Cabin in Milwaukie

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.

KitchenIndoor spacesParking

4.98 out of 5 average rating, 377 reviews

A spacious living area features light green walls and hardwood flooring. A gray sofa and a blue accent chair offer comfortable seating, complemented by a wooden coffee table. The open kitchen is visible in the background, showcasing modern appliances and warm wood cabinetry.

Guesthouse in Milwaukie

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.

Indoor spacesKitchenOutdoor spaces

4.95 out of 5 average rating, 422 reviews

A cozy living space features a beige sectional sofa adorned with colorful cushions, alongside a table set with a floral tablecloth. Poster art is displayed on the walls above, while a small window allows natural light into the area. A staircase leads to an upper level.

Guest suite in Portland

Miller Street Sellwood Garden Apartment

Cozy one-bedroom basement apartment in a quiet neighborhood. Queen-bed. Decorated with art from my travels in Turkey, Colombia, China and Egypt with descriptions in the AirBNB binder. No stove but small refrigerator, microwave and toaster and sink. Cabinet with plates, cups, silverware. Board and card games in cabinet below the TV. Have Hulu, Netflix, and Prime Video for your entertainment. Your own washer-dryer in the unit.

FamilyKitchenValue

A comfortably appointed studio features a queen bed with decorative pillows and a soft blanket. A seating area includes a modern chair beside a sleek storage unit, with a coffee setup and a mini refrigerator. Natural light filters through sheer curtains, enhancing a relaxed atmosphere.

4.96 out of 5 average rating, 291 reviews

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.

FamilyKitchenParking

The exterior showcases a red house featuring a bright yellow door. Two colorful chairs are placed beside a small table adorned with potted flowers. Lush greenery surrounds the area, with a stone walkway leading up to the entrance.

4.97 out of 5 average rating, 297 reviews

Lovely Art Filled Home 15 min to Downtown

This comfortable and newly remodeled home sits on a quiet residential street in the Ardenwald neighborhood a few blocks from the Portland border in Milwaukie. It's thoughtfully decorated throughout with local original artwork that's been curated by us, also artists! The trendy Sellwood and Woodstock neighborhoods are a little over a mile away filled with locally owned shops, bars, and restaurants.

KitchenIndoor spacesHiking

Popular amenities for Milwaukie family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.88 out of 5 average rating, 262 reviews

A bedroom features a queen bed with a decorative metal frame, dressed in light bedding with green accents. Two bedside lamps provide gentle illumination, and French doors open to a balcony, offering views of the surrounding greenery. Soft carpeting adds warmth to the space.

Apartment in Milwaukie

Indulge in Rare Riverside Retreat

FamilyKitchenWalkability

Superhost

The exterior of a blue stand-alone house is presented, featuring a well-maintained yard and a prominent tree at the center. A paved driveway leads to the entrance. The surrounding wooden fence adds privacy, while a planter box enhances the landscaping.

4.86 out of 5 average rating, 117 reviews

Spacious house with fenced yard and hot tub

KitchenIndoor spacesPets

Home in Southwest Portland

A mid-century living space features high vaulted wood ceilings and large windows that invite natural light. A leather sofa and patterned rug provide comfort, while a kitchen island with bar stools enhances functionality. Artwork adorns the wall, adding a touch of character to the room.

Portland Modern

FamilyKitchenAir conditioning

4.96 out of 5 average rating, 169 reviews

4.85 out of 5 average rating, 271 reviews

The entrance features a covered porch with a wooden frame and decorative pillars. Colorful flower baskets and potted plants adorn the space, while a bench rests on the wooden deck. Large windows provide visibility into the home, enhancing the welcoming appearance.

Home in Clackamas County

Miranda's Lodge- cozy place with hot tub

Indoor spacesKitchenGetting around

4.97 out of 5 average rating, 306 reviews

A tranquil guest house is nestled alongside a serene river, framed by tall trees with autumn foliage. Sunlight filters through the leaves, illuminating the exterior of the house while reflecting off the calm water, creating a peaceful ambiance.

Guesthouse in Clackamas

Luxurious Riverfront GuestHouse, Sauna & HotTub.

Indoor spacesKitchenAccess

4.83 out of 5 average rating, 546 reviews

Treehouse in Portland

Yeti's Tree House: Where Dreams Come True

FamilyIndoor spacesAmenities

4.91 out of 5 average rating, 155 reviews

A hot tub is positioned on a deck, offering a view of a vibrant sunset beyond a modern home. Trees frame the scene, with soft lighting adorning the structure. The silhouette of a spiral staircase adds depth to the setting.

Home in Happy Valley

RoofTop FirePit, HotTub & Outdoor Theater

Indoor spacesKitchenComfort

4.99 out of 5 average rating, 617 reviews

The guest home is set behind a picturesque entrance adorned with an elegant gate and carefully arranged greenery. Paved stone pathways guide visitors through the lush surroundings, leading to the welcoming facade of the home, seamlessly integrated with the tranquil, tree-lined environment.

Guest suite in Portland

IndigoBirch: Luxurious Zen Garden Retreat: Hot Tub

Indoor spacesKitchenGetting around

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 168 reviews

The open living space features a sectional couch with cushions, a wooden dining table, and chairs in a well-lit area. A television is mounted on the wall, with kitchen and dining areas visible in the background, illuminated by natural light from large windows.

Home in Gladstone

Forested Hygge House Getaway

KitchenIndoor spacesLayout

4.94 out of 5 average rating, 345 reviews

A modern studio space features a sleek sofa positioned across from a television on a stylish cabinet. The kitchen area is to the left, complemented by a small dining table with a striped rug underneath. Natural light enters through three narrow windows above.

Tiny home in Portland

Stumptown Cottage in Eastmoreland

KitchenIndoor spacesTV

4.92 out of 5 average rating, 481 reviews

A charming guesthouse is nestled within a lush garden, surrounded by colorful flowering bushes and sculpted hedges. The structure features large windows that offer a glimpse of the serene interior. The path leading to the guesthouse is intertwined with greenery, enhancing the tranquil atmosphere.

Cottage in Portland

Secret Garden Guesthouse!!

FamilyKitchenOutdoor spaces

4.9 out of 5 average rating, 154 reviews

A compact kitchenette features green cabinetry, a wooden countertop, and open shelving. A white refrigerator stands beside the counter, which includes a sink and a kettle. Decorative bowls are arranged on the shelves, all set against a leaf-patterned wallpaper.

Guest suite in Portland

Cozy Sellwood District Studio

KitchenIndoor spacesShared spaces

4.86 out of 5 average rating, 193 reviews

A bright living area features a red sectional sofa adorned with decorative throw pillows. Two pieces of abstract wall art add color, while a wooden side table sits beside the sofa. Light enters through a window, enhancing the space's warmth.

Holiday home in Portland

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

Indoor spacesKitchenWalkability

Apartment in Southwest Portland

The living area features a sofa in soft pink, complemented by a light gray chair. A coffee table with a decorative arrangement sits on a patterned rug. Natural light pours in through large windows adorned with light curtains, while a modern TV is mounted above a sleek black fireplace.

Mid-Century Hillsdale Retreat

Indoor spacesKitchenAir conditioning

4.98 out of 5 average rating, 182 reviews

4.98 out of 5 average rating, 482 reviews

A charming exterior of a single-story home is surrounded by lush green lawn and colorful flower beds. Large windows allow natural light to fill the interior. A welcoming front entrance features a classic door beneath a small overhang.

Apartment in Portland

Elegant SE Portland/Reed College BLUE MOON SUITE

Indoor spacesFamilyQuiet

4.93 out of 5 average rating, 443 reviews

Guesthouse in Portland

Woodstock•Net Zero•Chef Kitchen•Firepit•Pet-OK

FamilyIndoor spacesBiking

Family-friendly home rentals with a pool

Guesthouse in Southwest Portland

Cottage

Indoor spacesKitchenBackyard

4.99 out of 5 average rating, 105 reviews

4.97 out of 5 average rating, 399 reviews

A cozy sleeping space features a spacious bed adorned with various patterned pillows and a chunky knit blanket. A small yellow ottoman sits beside the bed, while artwork in soft colors is displayed on the light gray walls. A light rug adds warmth to the floor.

Cottage in Portland

Sellwood Sanctuary Guest House

Indoor spacesFamilyComfort

4.99 out of 5 average rating, 117 reviews

A spacious living area is highlighted by a warm brown leather seating arrangement, including two armchairs and a three-seat sofa. Natural light filters through the dual windows with rolled shades, complemented by two potted plants and a contemporary area rug.

Home in Portland

Corner of Heaven

FamilyIndoor spacesBackyard

4.96 out of 5 average rating, 181 reviews

Home in Vancouver

The Starburst Inn: Enclosed Heated Pool, Theater

KitchenIndoor spacesAir conditioning

4.97 out of 5 average rating, 109 reviews

Home in North Plains

1BR - Private House, Pool, Hot Tub & Forest Trails

Indoor spacesKitchenPool

4.92 out of 5 average rating, 678 reviews

A serene garden scene features a waterfall cascading over natural stone, surrounded by lush greenery and colorful flowers. A small pond is visible at the base of the waterfall, complemented by a tranquil statue. Various plants add vibrant textures and colors throughout the landscape.

Guest suite in Damascus

Oasis Between City, River & Mountain. Damascus OR

KitchenFamilyShared spaces

Guesthouse in Northwest Portland

The guest house is set against a lush backdrop of greenery, featuring large windows that provide views of the surrounding nature. A pool is positioned in front, accompanied by two wooden lounge chairs and a shaded umbrella, creating a serene outdoor relaxation area.

Poolhouse of Portland Architectural Gem

KitchenIndoor spacesOutdoor spaces

4.92 out of 5 average rating, 115 reviews