Family-friendly holiday 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.

Family · Kitchen · Laundry

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.

Indoor spaces · Kitchen · Comfort

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.

Indoor spaces · Kitchen · Condition

#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.

Indoor spaces · Family · Getting around

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.

Indoor spaces · Kitchen · Bathroom

~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.

Indoor spaces · Family · Cleanliness

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.

Kitchen · Indoor spaces · Comfort

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 October 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.

Kitchen · Family · Condition

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.

Family · Indoor spaces · Check-in

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.

Indoor spaces · Kitchen · TV

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.

Kitchen · Indoor spaces · Accuracy

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

Family · Indoor spaces · Value