Family-friendly holiday rentals in Oak Grove

4.97 out of 5 average rating, 184 reviews

An open living area features wooden ceiling beams and large windows that offer views of the surrounding trees. A comfortable sofa sits beside a wooden table. The kitchen area includes modern appliances and white cabinetry, enhancing the space's functionality.

Guesthouse in West Linn

Charming one bedroom apartment in the forest.

This unique apartment above a garage/shop , detached from the main house. Tucked away into a urban forest. I call it Our Robin's Nest because you look out on to branches of large fir trees. It is very private , yet Starbucks is right next door. Private entry and off street parking. This space has everything you need full kitchen, washer&dryer, queen size bed and fold out couch , plus a Play and Pack for the Littles. Walkable neighborhood , parks market and restaurants within walking distance.

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, 459 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.

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, 194 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.

4.95 out of 5 average rating, 134 reviews

The modern two-story home features a light exterior with vertical siding and a covered porch. Two chairs are positioned near the entrance, while vibrant pumpkins and landscaped flowers enhance the welcoming atmosphere. A garage is visible to the right.

Home in Oak Grove

Cozy, Modern Farmhouse, King Bed, Great Yard, Pets

Enjoy your stay in the quaint, Oak Grove neighborhood of Portland a block from the old historic trolly trail. Minutes to the river, close to downtown, ample dog parks make this spot perfect for your getaway. Our family poured our hearts into designing a modern and cozy space that our family loves to visit. We're so very excited that we get to share that with you! We've got a yard that the whole family will love and I know you'll make some priceless memories here, just as we have. Welcome!

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, 105 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.

Guesthouse in Lake Oswego

The kitchen features white cabinetry and a modern countertop with a sink. A coffee maker and tea kettle are visible. Natural light fills the space through nearby windows. A cozy living area can be seen in the background, adding warmth to the environment.

Secluded Willamette River Apartment in Lake Oswego

Enjoy a private stay full of nature with a river view! Newly remodeled 1 bedroom private apartment secluded and quiet. Apt is completely separate from main house. 10 min wlk to Mary's Woods Ret. Comm, 20 mins to George Rogers Park, 10 more to DT Lake Oswego w/shops, restaurants and theaters. Private, wooded property along the Willamette River. Fully rmld kit. & BR, LR with large 50” Smart TV, fast wifi. Q-bed + twin in sunroom, table/work area + wa/dr below. 8 stair entrance at back.

4.97 out of 5 average rating, 135 reviews

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, 106 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 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

4.94 out of 5 average rating, 503 reviews

A welcoming entrance features a vibrant red door bordered by large planters filled with green plants. Flanking the sides are bamboo and ferns, creating a calming atmosphere. The pathway leads to the entrance, showcasing a serene, nature-inspired setting.

Cottage in West Linn

Sunlit Oasis

This private, renovated art studio has skylights and quiet views of nature. As an interior designer, I loved creating a space that is as much an experience as a night away from home...and only 10 miles from downtown Portland! Please be advised that until September 2026, there will be construction on three homes behind our cottage. Work can begin at 7:00AM-7:00PM Mon-Fri., 9:00AM-5:00PM Sat.-Sun. There could be noise during those hours, which is out of our control.

4.97 out of 5 average rating, 134 reviews

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.

Home in Milwaukie

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!

4.92 out of 5 average rating, 478 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!!

Secret garden guesthouse is located 1 mile from downtown Lake Oswego and 2 miles from Lewis and Clark. Ideal hideaway for parents weekend, visiting the college, or guest lecturers. Also great location for exploring the amazing city of Portland and its surrounds. 50 minutes to Mt Hood, 40 minutes to wine country! Located in SW Portland and just a few miles from downtown Portland food scene. 1 mile from Lake Oswego. Friendly pets are welcome with a $40 pet fee.

4.89 out of 5 average rating, 768 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.

4.98 out of 5 average rating, 373 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.

Popular amenities for Oak Grove family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 298 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.

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.

Home in Milwaukie

Spacious house with fenced yard and hot tub

4.88 out of 5 average rating, 115 reviews

4.85 out of 5 average rating, 267 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

4.91 out of 5 average rating, 152 reviews

A fire pit is illuminated in the foreground, casting warm light on the surrounding stones. In the background, a colorful sunset paints the sky with shades of orange and pink, while trees and distant hills create a serene landscape.

Home in Happy Valley

RoofTop FirePit, HotTub & Outdoor Theater

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

4.96 out of 5 average rating, 165 reviews

4.83 out of 5 average rating, 538 reviews

Treehouse in Portland

Yeti's Tree House: Where Dreams Come True

4.99 out of 5 average rating, 124 reviews

A rustic wooden house, framed by trees, is complemented by a spacious patio area featuring outdoor seating. The entrance is adorned with bushes and climbing vines, creating a harmonious connection with the surrounding nature.

Cabin in Boring

7-acre Private Creekfront Oasis w sauna + hot tub

Home in Southwest Portland

Rock N Roll House + Hot Tub

4.97 out of 5 average rating, 313 reviews

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 121 reviews

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.

Home in Milwaukie

Secluded Studio

Superhost

The entrance features a welcoming design with a small bicycle parked beside a potted plant. A doormat with the word 'WELCOME' is placed at the threshold, leading into a bright and inviting interior visible through the open door.

Home in Lake Oswego

#StayInMyDistrict Lake Oswego Honey Bee Cottage

4.89 out of 5 average rating, 160 reviews

4.87 out of 5 average rating, 206 reviews

A well-maintained path leads to the entrance of the cottage, surrounded by lush greenery and vibrant flowering shrubs. The rustic exterior is complemented by a sunlit porch, offering a welcoming entryway into a tranquil outdoor space.

Cottage in West Linn

The Bee Cottage

Guest suite in Lake Oswego

A cozy sleeping area features a spacious bed dressed in crisp white linens. A large window allows natural light to fill the room, framed by soft gray curtains. A flat-screen television is mounted on the wall opposite, and a small table holds a decorative plant.

Peaceful Tree-Lined, Private ADU Retreat

4.95 out of 5 average rating, 172 reviews

4.94 out of 5 average rating, 127 reviews

A serene view of the river at sunset is captured, with vibrant colors reflecting off the water. Lush greenery lines the riverbanks, creating a natural border. The scene illustrates a tranquil atmosphere, ideal for relaxation and connection with nature.

Cottage in West Linn

Willamette Riverfront Cottage near Portland

4.85 out of 5 average rating, 272 reviews

A modern kitchen is highlighted by sleek cabinetry and stainless steel appliances. A spacious island with seating invites gatherings while abundant natural light streams through large windows, illuminating the counters. A dining set completes the area, offering a comfortable space for meals.

Home in Tualatin

Charming Urban Farm House - 24 hour self check in

Guesthouse in Wilsonville

Willow Creek Cottage

4.95 out of 5 average rating, 617 reviews

4.93 out of 5 average rating, 278 reviews

The exterior of the home is surrounded by a lush green lawn dotted with blooming trees, enhancing the tranquil country atmosphere. The two-story house features a welcoming entrance with large windows, inviting natural light into the spacious interior.

Home in Cedar Hills

Country Retreat Near Nike • 6BR 3400 SF • 15% off

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 127 reviews

A covered patio area features a modern grill adjacent to a fire pit with flames flickering over stone. Comfortable seating is arranged around the fire pit, surrounded by lush greenery and stacked firewood along the back wall.

Apartment in Beaverton

Recreational Family Fun & Adventures Await

Guesthouse in Southwest Portland

Cottage

4.99 out of 5 average rating, 103 reviews

4.91 out of 5 average rating, 125 reviews

Villa in Camas

The blueberry villa spa & heated pool

4.92 out of 5 average rating, 670 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

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

4.92 out of 5 average rating, 111 reviews

4.97 out of 5 average rating, 396 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

4.99 out of 5 average rating, 116 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