Family-friendly vacation rentals in Lake Oswego

Guesthouse in Southwest Portland

Oswego Empty Nest

The Oswego Empty Nest is a newly remodeled, cozy, one bedroom unit located in Lake Oswego with a private entrance and 500 sq ft of living space. Prepare your own meals in the beautiful full kitchen. Relax, work or entertain yourself in the living space with a large TV with Roku or rest in the quiet comfortable bedroom with an en suite bathroom. Easy access to restaurants, New Seasons, Columbia Outlet, and hiking trails all within walking distance. Close to downtown and quick airport access.

5.0 out of 5 average rating, 166 reviews

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.

Guesthouse in Southwest Portland

A tree-lined pathway leads to a wooden staircase bordered by blooming flowers. The pathway features a gentle slope with a railing, guiding visitors toward a secluded entrance nestled among greenery. Lush foliage and vibrant blooms provide a natural, tranquil setting.

Cozy and Charming

The studio unit has a queen size bed equipped with full kitchen and bathroom as well as working area with wifi and HBO, Showtime. It has separate entrance and located at secluded hilly area. There are 8-9 steps to the unit and maybe difficult for some guests. Washer/dryer are in the house, guests can let us know if they like to use. During a winter snow/ice storm, our location can be challenging. You may need to cancel or change your reservation accordingly if there are snow/ice storm.

4.96 out of 5 average rating, 424 reviews

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

#StayinMyDistrict Lake Oswego Honey Bee Cottage. Live like a local while experiencing the trendy Lake Oswego District! 5 blks to coffee shops, restaurants, shopping & local hot spots! Convenient to West Linn, SW Portland & Tigard Neighborhoods. Private Cottage nestled in the trees, and furnished to create a comfortable and charming space! Historic 1 bed/1bath (+sofa bed & Futon) King Suite, Kitchen, W/D, Private Patio & Fenced Yard. FREE Parking. Pre-Approved Dogs w/addt’l $50 per pet fee.

4.89 out of 5 average rating, 160 reviews

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

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.

Guest suite in Southwest Portland

A neatly arranged bedroom features a white metal headboard with soft linens. A pillow with 'Aloha' is centered on the bed. A bedside lamp and a small table book are visible next to the bed, complemented by a subtle wall design that adds texture.

~Clean Aloha House in Lovely Lake Oswego~

Aloha! Welcome to your quiet, relaxing getaway You’ll have private access to your bedroom, bathroom, living room, and kitchenette. The entire lower level of our home is yours. The host may occasionally need access to the w/d in your unit, but we will always communicate first and be non-intrusive. Please note, we are a quiet family living above, so you may hear footsteps. We do have a golden retriever who is EXTREMELY friendly. He might bark when you arrive to say hello.

4.86 out of 5 average rating, 243 reviews

5.0 out of 5 average rating, 114 reviews

Apartment in Lake Oswego

Pheasant Hill Carriage House

Pheasant Hill Carriage House has been described by guests as " Better than a five-star hotel -- you won't want to leave." We provide the best in hospitality, the amenities of home in a beautiful park-like setting, and a relaxing night's sleep in a premium king-sized bed, . Great for an extended business trip or a romantic getaway. Private entrance, high-speed Wi-Fi, central air, professional quality exercise equipment, full-sized kitchen, full-sized washer and dryer.

Guest suite in Lake Oswego

A living area is shown with comfortable seating, featuring a large television mounted on the wall. A dining table is set for four, surrounded by natural wood chairs. Decorative plants and framed artwork add warmth to the inviting space.

Peaceful 2 Bdrm Suite 1000 sq ft. Upscale Location

Your home away from home includes your own suite of 2 bedrooms, a beautiful kitchen & living area, & bathroom. The home is in a quiet, safe & friendly neighborhood with scenic hiking trails just out the back door. There are several shopping complexes less than 2 miles away. Amenities include high end linens, HD cable pkg, broadcast networks, Netflix & Amazon Prime. 5 min off of I-5 freeway, approx. 15 min to downtown Portland, 10 min to Lewis & Clark college.

4.94 out of 5 average rating, 307 reviews

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.

4.85 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

This charming 2 story house that is a full time Airbnb home and has 5 bedrooms and was recently remodeled and resembles the charm of the tv show fixer upper. Huge yard, new hardwoods, remodeled kitchen, comfortable furniture and close to everything. 20 min to downtown. This house is a full time Airbnb listing, has super fast internet/wifi, has a Samsung SmartTV and is close to everything. 24hour self check in and check out. Tons of parking.

4.96 out of 5 average rating, 159 reviews

A single-story house with a welcoming front porch is surrounded by a lush, green lawn. The exterior features a mix of white siding and dark roofing, with two garage doors on one side. Tall trees provide a natural backdrop, enhancing the tranquil setting.

Home in Lake Oswego

Completely updated home in Lake Oswego!

I have a 3 bedroom, 2 full bath house with a family room, dinning area & open kitchen. The master has a king bed, the other two have queen beds, I also have an air mattress if additional sleep space is needed. All bedrooms have closets & TVs, there is a desk and chair for a work space if needed in garage. High speed internet and a fully fenced in back yard with a covered space, table and chairs for relaxing or entertaining.

Popular amenities for Lake Oswego family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.96 out of 5 average rating, 165 reviews

Portland Modern

4.95 out of 5 average rating, 459 reviews

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.

Guest suite in Milwaukie

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

4.97 out of 5 average rating, 313 reviews

Rock N Roll House + Hot Tub

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, 189 reviews

A charming craftsman home is framed by a white picket fence, with a welcoming front porch and a pergola overhead. The exterior features dark blue siding, three front-facing windows, and lush greenery surrounding the entrance.

Home in Sherwood

Old Town Retreat - Best place in Old Town Sherwood

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.

An outdoor space features a wooden pergola overhead, providing shade over a patio area. A small table is accompanied by two wooden chairs, while a cushioned seating area is visible on the raised platform. Lush greenery forms a natural backdrop.

4.87 out of 5 average rating, 229 reviews

Charming home on private street with hot tub

A spacious family room features a large L-shaped couch with comfortable seating. A plush green ottoman rests on a striped rug, complementing a contemporary armchair. Natural light filters through multiple windows, illuminating the room, which includes a TV and a cozy gas-lit fireplace.

4.93 out of 5 average rating, 300 reviews

Spacious Forest Retreat w/ Hot Tub & Views

Family- and pet-friendly home rentals

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

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

A charming outdoor area is visible, featuring a stone pathway leading to a cozy seating arrangement with two black chairs. The bungalow is framed by lush greenery, with warm light emanating from the windows, inviting a peaceful ambiance.

4.97 out of 5 average rating, 176 reviews

Multnomah Village Hideout

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

4.93 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

Guesthouse in Wilsonville

Willow Creek Cottage

4.95 out of 5 average rating, 617 reviews

Superhost

A welcoming living area features a modern gray sofa, accent table, and decorative plants. Warm lighting is provided by two floor lamps. A dining table with white chairs is visible, along with an elegant area rug. A sliding barn door leads to additional spaces.

Home in Tigard

Spectacular Choice: Sleeps 6, Your Dog Welcome Too

4.95 out of 5 average rating, 248 reviews

Apartment in Southwest Portland

The spacious living area features large windows that allow natural light to fill the room. A stylish seating arrangement is complemented by an accent chair and a coffee table, all set atop a decorative rug. A fireplace adds warmth to the inviting ambiance.

Mid-Century Hillsdale Retreat

4.98 out of 5 average rating, 179 reviews

Family-friendly home rentals with a pool

Guesthouse in Southwest Portland

Casetta

4.99 out of 5 average rating, 103 reviews

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 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

4.96 out of 5 average rating, 176 reviews

Home in Vancouver

The Starburst Inn: Enclosed Heated Pool, Theater

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

4.91 out of 5 average rating, 125 reviews

Villa in Camas

The blueberry villa spa & heated pool