Family-friendly vacation rentals in Lake Oswego

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.

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.

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.

#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.

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.

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.

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.

Charming Tiny Forest Home, PDX next to Lake Oswego

Relax at this serene Portland retreat on the Lake Oswego border, near Tryon Creek State Park and Lewis & Clark College in the prestigious Dunthorpe neighborhood. Explore the park, bike, hike, swim the river, and sample top local cuisine and wine at two of Willamette Valley’s best tasting rooms, all just minutes away in downtown Lake Oswego. A quick 10 minute drive takes you to downtown Portland and Portlandia! One-night weekend stays require approval.

Arbor Suite Apt - Washer/Dryer, Free Parking, Desk

There is a private entrance to this 725 sq ft. bright, CLEAN, and SANITIZED guest apartment within a home, in a well established neighborhood on the border of West Linn and Lake Oswego. Spacious, beautifully furnished one bedroom with an office/den (includes fiber optic internet & monitor ) in a quiet and desirable suburb of Portland that offers a lush treed garden with a gas fire pit and patio. YouTube TV available. Close to Mary's Woods!

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.

Luxury Lake Oswego Retreat - all new & great patio

Luxury Lake Oswego retreat just 3 blocks from George Rogers Park and New Seasons Market. This exceptional custom home, valued at over $1.2M, features 3 bedrooms (2 king, 1 queen), all-new upscale furnishings, a gourmet kitchen with a Jura E6 espresso machine, cozy gas fireplace, and a huge covered patio with a firepit, outdoor TV, and comfortable seating. Perfect for families seeking comfort, style, and an ideal location

The Hen Den

Light filled and cozy 600 sf private guest suite with private entry in a private garden setting. Grill up a burger or head down to the local French restaurant for some tasty food. Rent gear at the REI down the road and head to Mt. Hood for an adventure. Close to Bridgeport Mall and amazing restaurants with easy access to I-5, I-205 and I-117 to head to the coast, the Columbia River Gorge or downtown Portland.