Family-friendly holiday rentals in Portland

#StayInMyDistrict St Johns Walk to dining & shops

Stay in My District Downtown St Johns. Walk to local dining & shopping. Forest Park is across the bridge, with miles of single track running, hiking & Mtn biking trails. Walk or bike to Downtown St Johns, Cathedral Park, 10 min. to Downtown Portland & Pearl District. 20 min to PDX. NEW basement apt designed with guest comfort in mind. Modern finishes and upgrades in this comfortable 900 ft.² featuring 2 bed / 1 bath. Sleeps up to 5. Kitchen, Washer/Dryer, Fireplace. FREE Parking, Roku Streaming/

The Portland Villa on Alberta St

In the heart of NE Portland's vibrant and bustling Alberta Arts district. Endless options for dining, drinking, shopping and entertainment within walking distance. The main home is 2800 sqft plus an additional 1200 sqft on a private rooftop deck (that we built ourselves!). There is natural light (and plants) galore. Prepare meals in our chef’s kitchen. We don’t skimp on linens, supplies, cozy mattresses or bedding. A legally permitted rental by the City of Portland. 1% for The Planet member.

2 BR Family Friendly Luxury Suite in SE Woodstock

Constructed in 2017, enjoy our spacious 800-square-foot, private lower level apartment in our 1910 arts and crafts home in cozy Woodstock neighborhood in inner SE Portland. A short walk to Woodstock restaurants and grocery stores. Close to Reed College, Sellwood, SE Division and SE Hawthorne shops and restaurants. A short 20 min drive into downtown Portland and one block away from public transit. Comfortably sleeps up to 5 max. Height in some areas might inconvenience guests over 6'.

Huge Home with King Beds in Prime Spot with Views!

Architectural masterpiece on a safe, quiet street just blocks from Williams and Mississippi Ave, home to some of Portland’s best dining, drinking, shopping and more. Spread out across three spacious levels with multiple living areas, a large open kitchen with two eating bars, four king bedrooms and a bunk room (each with its own TV!), and 3.5 bathrooms. Relax and dine alfresco on the beautiful back patio, then watch sunrises and sunsets from the east and west facing roof decks!

Custom Comfort Home in West Linn, Oregon

Best suited to families or couples. Allergen free as possible. No fur, feathers, smoke, odors, mold, pesticides inside, or live plants. No animals permitted. Great entire upper level of home on a very large lot, two decks, with spacious off street parking, feng shui correct. Many trees. View to the east. Handicap ramp with parking from the rear to upper level. 30' parking space for RV, trailer, or boat, with electric. Guests who remain overnight must register also.

Home Away From Home

Our duplex is close to restaurants and family-friendly activities. We are located 4 blocks from downtown and one mile from George Fox University. You’ll love our location because of the proximity to parks, downtown Portland, and the coast. Our little home has all you'll need for a great stay: comfortable beds (Two Queen-size beds), kitchen and laundry facilities, local air TV, and Wi-Fi. Our place is good for couples, business travelers, and families.

Light and Bright, Cozy Woodstock Cottage

This beautiful 1bd, 1ba house is spacious and bright. It's in a quiet neighborhood, just a short walk to restaurants, coffee shops, farmer's market and gourmet grocery stores. Close to Reed College and several parks. It's also only 2 blocks from 2 bus lines, which makes getting around town a breeze. We are very family friendly and happy to help answer any questions, or give recommendations in order to ensure you enjoy your stay!

Alberta Arts Bungalow - 4 Bedroom

We are a legally permitted 4 bedroom short term rental house. Alberta Arts district is unique; rich in culture, excellent food and drink, on transit lines and totally walkable. We're half a block from it all. At home, enjoy the whole single level house, impeccably clean, modern and comfortable, with solid bamboo floors. Enjoy the front porch and private back yard. Our tenant lives upstairs in a separate apartment.

La Petite- BRAND NEW!

ELEGANT URBAN OASIS IN PORTLAND'S DIVISION NEIGHBORHOOD. Step into an enclave of opulence and comfort in our newly designed Accessory Dwelling Unit (ADU). This private haven, sculpted with attention to every detail, stands as a testament to luxury and comfort, offering you Portland's finest in an intimate, and sleek setting. You'll cherish our ADU's tranquil ambiance and our foodie forward neighborhood.