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.

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.

Brand New Tiny Home/Pottery Studio in Cute Village

Welcome to DARK MODE, the tiny home/pottery studio 2 blocks from adorable Multnomah Village. Find peace in this serene hidden backyard oasis. Unit is 200 square feet plus loft and deck, behind the main house. Features include: - Jetted tub - Sleeping loft (queen) - Pull out bed (full) - Fire pit - Porch swing - Work desk - Cascading water feature - Outdoor dining table No kitchen but has a sink, fridge, microwave, water boiler, and plenty of wonderful food options within a few blocks.

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.

Lewis and Clark Hide-A-Way Apartment

Private entrance apartment in Southwest Portland near Lewis & Clark College, OHSU, Multnomah Village and Hillsdale. Large living room, full size kitchen. Extremely quite bedroom with queen bed, single roll away bed and pak-n-play bed available. Large outdoor patio space with barbeque, play structure for children, fire pit and fenced yard. Quiet neighborhood, walking distance to Moonlight grill, Chez Jose Mexican, Tokyroll sushi, Tryon creek sports bar. Walking distance to Tryon Creek.

Spacious Forest Retreat w/ Hot Tub & Views

In the woods, next to a creek, but still in Portland! Forget your worries in this spacious and serene space. There is a private entrance to this large two story guest suite, which includes a family room, living area with dining area and kitchenette, bedroom and bathroom, central AC, and private balcony. Located in a quiet neighborhood, close to hiking trails in Woods Memorial Park. A 3-minute drive or 1 mile walk to popular Multnomah Village; 15 minutes from Downtown Portland.

Cottage in the Woods: SANITIZED! FULLY STOCKED!

Cute 500 sq foot cottage behind a main house, located on a 1/2 acre park-like setting lot on a dead end street. Quiet location, easy access to I-5, shopping, Lake Oswego, hiking, and the Tualatin River. The cottage has one bedroom w/ a queen bed, blow up queen mattress, and a large couch. The large fir trees on the property attract many birds and squirrels. We also have a flock of neighborhood peacocks that visit!

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.

Signal House – Light Up The Portal

Signal House is an immersive art home from The Book of Houses in Pudding Heroes – a living chapter of the story. It is an overnight experiential stay, for travelers looking to jump off to the next dimension. Our 3 room home's highlight is the fully mirrored experience with sound /mood lighting for play & sleep. We have a cat meme lounging experience in the media room. 15 minutes from Portland on I-5.

Portland Cottage with Kitchenette

Our cottage is in a quiet southwest Portland neighborhood. It includes a pillow top queen size bed, microwave, refrigerator, Keurig coffee maker, toaster oven, 2 burner hotplate, hair dryer, soap & shampoo. Easy access to I-5 and downtown Portland by car or public transportation.