
Family-friendly vacation rentals in Gladstone
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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*

Artistic Boho Romantic Woodshed
This warm and cozy close-in country sanctuary is like nothing you've EVER seen! If you like affordable ultimate glamping, then look no further! The fire pit, creative décor, heat pump, table/chairs, weekly serviced private portapotty (equals most of cleaning fee), sink, HD TV, WiFi, Alexa, outdoor covered heated shower w/view, AND 2 friendly Scottish Highland cows you can feed and interact with! We welcome ALL colors, religions, LGBTQ , Cannabis friendly! Cigs OK by fire pit only.

The River House - Waterfront Retreat w/Fireplace
Experience the serenity of riverside living in our private, enchanting retreat nestled on the tranquil banks of the Clackamas River. This guest suite offers 1500 square feet of living space, boasting a private entrance and a spacious deck that grants breathtaking views of both the serene pond and the majestic river. Step inside to discover a haven of comfort and elegance. The gourmet kitchen features SS appliances, sleek granite countertops, and is fully stocked for your culinary needs.

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.

Rustic Creekside Cabin
This tranquil hideaway feels like you're in the middle of the forest, but is just minutes from Portland. Relax next to the burbling creek surrounded by towering cedar trees. The MAX Orange line and downtown Milwaukie are only five minutes away. Built in 1928, the cabin has one bedroom and bathroom, living room, full kitchen and central heat. The bedroom has one queen bed and an en suite bathroom. There is a pull-out queen futon in the living room.

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

Glamping Bliss ~ 5 Acre Secluded Forest Oasis

Private River Cottage with Hot Tub and beach!

Spacious Forest Retreat w/ Hot Tub & Views

Sunday Quiet, awesome Hood view, hot tub!

Margaux | Airstream Glamping in the Heart of PDX

The Playground

Fireshaker Guesthouse (with hot tub!)

Portland Modern
Family- and pet-friendly home rentals

Secret Garden Guesthouse!!

Beaverton Vintage Tiny Home

Charming Remodeled Home in SE

Charming Fall Winery Getaway ~ Comfy and Cozy

Clean & Cozy "Private" Studio Suite

Lovely 1-bed vacation home w/ off street parking.

Oak Grove Easy-Centrally located w/King Bed

Willow Creek Cottage
Family-friendly home rentals with a pool

Cascadia Cabana | Poolside Suite with Spa

Oasis Between City, River & Mountain. Damascus OR

Rose City Retreat

Garden Apartment in the Heart of Portland

Quaint Tiny House In The Trees. Damascus, Oregon.

Wine Country Spa House - Hot Tub/Sauna/Pool

Beautiful, Magical, Treehouse

Rose City Hideaway
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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 R1,739Â 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