
Family-friendly vacation rentals in Gladstone
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Gladstone
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.

Forested Hygge House Getaway
Relax in a Gladstone oasis overlooking an untouched trail and forested area. A cozy, bright, and private spot. I hope you connect with my affinity for vintage art and clean lines! You’ll have the entire house and 1/3 acre to yourself. Less than 30 mins from most anywhere in Portland Metro, 10 mins to Oregon City, and 1 hr to Mt. Hood. This is a dog friendly (no cats), non-smoking house. The large yard is on a dead-end street, though not fenced. *Not ideal for those with mobility issues*

The Wee Humble Cottage
Cozy 1 bed, 1 bath, 100 yr old smoke/vape free cottage is conveniently located in Gladstone, OR; walking distance to local shops & antique mercantile. Within blocks of the confluence the Clackamas & Willamette Rivers. Just 1.5 mi from historic downtown Oregon City Main Street, Willamette Falls, Abernethy Center & End of the Oregon Trail Museum. Also conveniently located near the Trolley Trail Loop, a 19 mile long meandering walking/cycling trail through a series of quiet communities.

The Room In Between
Private and secure entrance to this modern and 5-Star space! Comfortable Queen Murphy bed that converts to a sofa. Fast Wifi and Smart TV w/access to Netflix & Prime Video. Fenced yard with security gate entrance, off of private paved driveway, to lead you to your own private patio & room entrance. Self check-in is at 2pm or later. Check out is 11am. No pets. Smoking allowed on the outside patio only. Flat entrance pathway is well lit from your parking space to your room & patio.

Riverside Cottage Apartment.
Charming cottage apartment on a hill next to the Willamette River, 30 mins from downtown Portland. Relax, and enjoy the quiet and peaceful surroundings. Fully stocked kitchen. Fast wifi at 50 Mbps. Cozy inside in the wintertime, also with a park-like setting with walking access down the lush backyard to the river where you can enjoy swimming, fishing, kayaking, and bird watching. You can use the shared recreation room with ping pong, pool table, shuffleboard, and weights.

Light Filled Garden Studio
Our wonderfully bright garden studio is perfect for a short stay or for visitors looking to explore Portland for an extended visit. It has a full, well-stocked kitchen, ideal for those looking to stay in and cook, but it’s also just a 20 minute drive from downtown, for those looking to explore the wonderful restaurant scene Portland offers. Keyless entry and private entrance through the side yard gate provide renters with complete autonomy during their visit.

Oasis Between City, River & Mountain. Damascus OR
A large & private guest house on lower level of home only 30 min. to Portland. Mt. Hood, Gorge Waterfalls & Scenic hikes within 60 min drive. Super comfortable bed, quiet nights, recliner sofa & relaxing atmosphere make this an ideal place to hang out and rest. We welcome ALL colors, LGBTQ. Must Read all info, house rules & details prior to booking please. Informed guests are happy guests. Can accommodate 3pm check in every day of the week except Tuesdays.

Quaint Tiny House In The Trees. Damascus, Oregon.
150 ft. walk down a steep driveway takes you to a unique private little studio with everything an adventurous spirit needs. You must be in physically good shape to handle this location. We have friendly dogs you may see outside. 30 min. to SE Portland, 45 to PDX, One hour to Mt. Hood, 40 min to waterfalls in the Columbia Gorge. Pool open June 15 through September 5th. Can accommodate a 3pm check-in all days except Tuesdays.

Milwaukie Retreat in the Woods
Your private apartment is located on a wood filled lot with a private outdoor area, shade and even deer on occasion. We are 12 miles from the airport, near freeways with easy access to downtown, and to make your way to the coast or the Columbia Gorge, Mt Hood and the Willamette Valley for wine tasting. We have added extra cleaning procedures to help fight against Covid 19.

Tiny Sequoia House
Feel refreshed when you stay in this rustic gem. With a full heated outdoor yet private shower, lofted queen bed and fold-out couch, walking distance to tons of restaurants and shops, 15 - 25 minutes into Portland proper depending on where you're going and very close to the wilderness and hiking.

Why Not Stay?
This charming Basement Apartment is in a beautiful Ranch Style home in a quiet tree lined neighborhood of Milwaukie, Oregon. It offers it's own ground level entrance from an ample parking area. You will have a private bedroom, bath and kitchenette.

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!
Popular amenities for Gladstone family-friendly rentals
Family-friendly home rentals with a hot tub

Muse Cabin in old growth forest w/cedar hot tub

Spacious Forest Retreat w/ Hot Tub & Views

Sunday Quiet, awesome Hood view, hot tub!

Margaux | Airstream Glamping in the Heart of PDX

The Playground

Portland Modern

Fireshaker Guesthouse (with hot tub!)

Luxurious Riverfront GuestHouse, Sauna & HotTub.
Family- and pet-friendly home rentals

The Cedar Cottage

Beaverton Vintage Tiny Home

Spacious Loft in the Heart of Southeast PDX

Oak Grove Easy-Centrally located w/King Bed

Willow Creek Cottage

Country Living in a Forest Setting

Hawthorne Division Food Drink Tabor Wonderland

Secluded Willamette River Apartment in Lake Oswego
Family-friendly home rentals with a pool

Cascadia Cabana | Poolside Suite with Spa

Rose City Retreat

Garden Apartment in the Heart of Portland

Beautiful, Magical, Treehouse

Wine Country Spa House - Hot Tub/Sauna/Pool

Rose City Hideaway

Secluded Suite Surrounded in Beauty

Poolhouse of Portland Architectural Gem
Quick stats about vacation rentals that are family-friendly in Gladstone

Total vacation rentals
Explore 20 vacation rentals in Gladstone

Nightly prices starting at
Gladstone vacation rentals start at R1,733 ZAR per night before taxes and fees

Verified guest reviews
Over 800 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Gladstone vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Gladstone rentals

4.9 Average rating
Gladstone stays are highly rated by guests—averaging 4.9 out of 5!
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- Moda Center
- Laurelhurst Park
- Oregon Zoo
- Enchanted Forest
- Timberline Lodge
- Providence Park
- The Grotto
- Silver Falls State Park
- Portland Japanese Garden
- Mt. Hood Skibowl
- Wooden Shoe Tulip Festival
- Beacon Rock State Park
- Wonder Ballroom
- Mt. Hood Meadows
- Hoyt Arboretum
- Powell's City of Books
- Tom McCall Waterfront Park
- Cooper Spur Family Ski Area
- Oaks Amusement Park
- Pumpkin Ridge Golf Club
- Wings & Waves Waterpark
- Portland Art Museum
- Domaine Serene
- Skamania Lodge Golf Course