Family-friendly holiday rentals in Portland Downtown

Bright 1BR - Walk to Coffee, Food & Shopping

✨ Bright 1BR in Walkable NW 23rd — Steps to Everything ✨ 🏙️ Heart of Portland's trendiest shopping & dining district 🛏️ Queen bed in private bedroom 🍳 Full kitchen with oven, stove & coffee maker 📺 Smart TV & fast WiFi throughout 💼 Laptop-friendly workspace for remote work 🐾 Pet-friendly — bring your furry friend ❄️ AC & heating for year-round comfort 🔑 Private entrance, no shared spaces — entirely yours 🪜 Steep exterior stairs to enter (not step-free) 🍽️ Steps from NW 23rd's top resta

Yeti's Tree House: Where Dreams Come True

"Thank you for creating such a magical place..." Recent Guest "Best Tree House I've ever seen!" Recent Guest Let the kid in you come to play in this real treehouse held up by four trees, 18 feet off the ground. Zip line down or take a giant soaking tub. A magical stroll through the woods leads to the suspension bridge. You won't believe you're only minutes from town. Wear appropriate shoes as it is a short 2-minute hike to the tree house. At times, it can get a little slick.

Accessible, AIA-Award Winning, Urban Garden Oasis

A nurturing place with abundant light, garden views, & access to the best Portland food. “The best Airbnb I’ve ever stayed in!” - frequent guest comment. - American Institute of Architects Award to designer Webster Wilson - Upscale amenities & European fixtures - Quiet NoPo neighborhood tree-lined street, minutes from downtown - Fully equipped kitchen w/ fresh local coffee - Indoor & outdoor dining - See photo captions for more details - Trained Service Animals welcome; no pets nor ESAs

Chic Belmont retreat w/tree views & king bed!

Experience weird and wonderful SE Portland from a serene, newly-built home in a walkable/bikeable neighborhood with king bed and lots of light! Wake up well rested and open curtain on floor to ceiling windows to morning light. Enjoy the full kitchen & soaker tub in a breathtaking architect-designed home perfect for foodies, couples, and remote work. Great location just steps from bakeries, shops, parks and taprooms. Discover the quirky character and trendy eats of Belmont-Hawthorne-Tabor!

Luxury Cabin in the City

Modern cabin in the city built from the ground up for peace and serenity! Giant skylights abound to make even the dreariest of days feel special, and if the sun is out there's no better spot in all of Portland to experience it! Join friends and family at Irving park for a picnic or a tennis match. Or, hop over to Williams and Mississippi for some of the best known restaurants in Portland. Very close to the convention and Moda center that give you tremendous options for entertainment.

Queen Anne Guest Apt. In Historic District

Discover a charming guesthouse apartment in the heart of Portland! This private retreat, nestled in a historic home, offers easy access to the city's vibrant scene. Explore the nearby NW 21st/23rd commercial districts, the Pearl District, and downtown Portland. Enjoy delicious dining, unique shops, and exciting entertainment, including the Timbers and Thorns soccer stadium. Perfect for leisure or business travelers seeking a comfortable and convenient stay.

NW 23rd - 1BR - Best Location - Historic Beauty

✨ Sunlit Suite Steps from NW 23rd Shopping & Dining ✨ 🌳 Timeless charm meets modern comfort in Portland's best neighborhood 🛏️ Cozy queen bed + plush sofa for two 🍳 Full kitchen with stove, oven & microwave 🛋️ Smart TV, fast WiFi & dedicated workspace 🐾 Pet-friendly — bring your furry friend ❄️ AC & heating for year-round comfort 🔒 Private entrance — entirely yours 🍽️ Steps from boutique shops, top restaurants & tree-lined streets.

Cozy, Stylish Bungalow w/ Fireplace & Full Kitchen

Enjoy a comfy retreat in this cozy and bright studio with a private bathroom, air conditioning, fireplace, full kitchen and work desk. Conveniently located within walking distance to local restaurants, coffee shops, retail stores, and parks. Centrally located in Portland and just 3 miles from downtown. Take a stroll through Historic Irvington and enjoy some of the most beautiful homes and old growth trees that Portland has to offer.

Modern Guesthouse in Portland's Central Eastside

Tall ceilings, an open staircase and walls of windows flood the space with light (even in Portland), while molded plywood Eames chairs add mid-century style. Located in the heart of Portland within walking distance to great restaurants, coffee and parks. Fast, gigabit fiber internet, full kitchen, large table, and private outdoor spaces help maximize your stay and comfort, whether you're alone or with a group. Editor's pick in Dwell.

Large Studio in Historic Isam White House

Super Clean third floor suite in the historic Isam White House. Includes bed area, living and dining area, kitchenette with microwave, hot water kettle, dishes and small fridge and private bathroom with tub/shower. This is one of the last grand mansions downtown that hasn't been converted to condos or offices. We are at the shopping and restaurant districts of Northwest 21st and 23rd Avenues. Walkability score of 97!

The Royal Scott Double Decker Bus

Our tiny home started life as a commuter bus in Manchester, England, in 1953, then did stints in San Francisco and Mt. St. Helens before finding a home as the Grilled Cheese Grill in Portland. Now it’s been reimagined as a mid century modern-inspired tiny home, with whimsical painting details from one of its former lives and fresh new handmade details that make it a cozy, inspiring stay. Find more on IG @smore.life

Explore Portland on Foot from Your Modern Retreat

Welcome to The LoftHaus. Stroll through a luscious landscaped garden and past a bubbling fountain to reach this light-filled, creative living space. A roll-up glass garage door in the bedroom offers a connection with the outside world while flooding the room with natural light. Accepting guests and implementing extra cleaning protocols. Excellent wireless internet speeds!