Family-friendly vacation rentals in Lake Oswego

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Top-rated family-friendly rentals in Lake Oswego

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

Guesthouse in Lake Oswego

5 out of 5 average rating, 140 reviews

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.

Top guest favorite

Guesthouse in West Linn

4.96 out of 5 average rating, 148 reviews

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.

Guest favorite

Guest suite in Milwaukie

4.91 out of 5 average rating, 336 reviews

Upstairs Rustic 1940s styled Studio Apartment

Great for water loving people! Private unit. Self checkin. Outdoor patio & yard. Wifi. Pet/animal free, allergy safe. Smoke free. Linens washed with Defunkify perfume free soap. Fully stocked kitchenette. .75 Bathroom (sink, toilet, large shower) Stocked w/ toiletries. AC in summer. Complimentary snacks! 1940's vintage furniture. Quiet neighborhood. Semi-industrial parking, as we run a pressure washing biz. Your unit is around the back on the 2nd floor. 1/4 mi to bus route at top of hill.

Guest favorite

Guesthouse in Multnomah

4.95 out of 5 average rating, 110 reviews

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.

Guest favorite

Guesthouse in West Portland Park

4.95 out of 5 average rating, 381 reviews

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.

Top guest favorite

Home in Beaverton-Hillsboro

4.93 out of 5 average rating, 125 reviews

#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.

Top guest favorite

Home in Beaverton-Hillsboro

4.97 out of 5 average rating, 138 reviews

Maple Cottage - Enchanting, Cozy and Private

Nestled on a quiet treed street in the upscale First Addition neighborhood of Lake Oswego, Maple Cottage is a tastefully decorated single level home waiting for you. Enjoy total privacy! Maple Cottage is cozy and clean. This beautiful 720 sq. ft. private cottage has two bedrooms, one bath, a fully equipped kitchen and a living room where you can relax. Stroll to restaurants, bars, shops, the local movie theater, parks, grocery store and more. First Addition is a walker's paradise.

Top guest favorite

Cottage in Lake Oswego

4.94 out of 5 average rating, 306 reviews

Peacock Grove Cottage in Lake Oswego, OR

Sunny, private one bedroom cottage in quiet, wooded neighborhood. Separate dwelling behind main house. Queen bed, sofa bed, TV, WiFi, A/C, full kitchen, washer & dryer, bathroom with shower and beautiful patio. One mile from I-5 and 8 miles to downtown Portland. Short drive to downtown Lake Oswego. Walking distance, just two blocks, to La Provence, Jefe, Zupans, Albertsons, Starbucks, Waluga Park. Perfect for families or the business traveler. Come stay!

Guest favorite

Home in Lake Oswego

4.89 out of 5 average rating, 176 reviews

“Sucker Creek Inn” - with partial lake view

This home is in a great location only a 10 minute walk to downtown Lake Oswego where you'll find a wide variety of restaurants, bars, and shopping. It's also just a five minute walk from the Willamette River, so bring your kayaks and SUPs to explore all that Lake Oswego has to offer, or take a short Uber ride (10 minutes) into downtown Portland. Lastly, the lot is next to one of the oldest homes in Lake Oswego- built when Lake Oswego was known as Sucker Creek

Top guest favorite

Guest suite in Lake Grove

4.93 out of 5 average rating, 690 reviews

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.

Guest favorite

Home in Lake Oswego

4.97 out of 5 average rating, 218 reviews

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.

Top guest favorite

Guesthouse in West Portland Park

4.96 out of 5 average rating, 677 reviews

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.