Guest house holiday rentals in Portland

Luxury Loft ~ Bidet, Skylight & Bed for Royalty

*We offer a 15% weekly stay discount and 20% monthly stay discount. *Photos of all businesses in this listing are < 1.0 mile away. *All Races, Gender Identities, Sexual Orientations, Religions Welcome. Our family welcomes you to a slice of our Portland life. We live in a quiet residential neighborhood where the sounds you are most likely to encounter are the distant squawks of our backyard chickens, the pitter-patter of raindrops on the skylight, or the occasional children's squeal or dog bark.

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.

Private urban retreat, new build, 1bedroom, sleep4

Relax in this calm, clean and simple space. Enter in from the sidewalk fence to a little patio great for enjoying your coffee and some fresh air. There is a full kitchen that opens into the living area with a skylight and high windows that offer great natural light. Walk down the hall and enjoy the spacious bathroom with our provided bath tray for real relaxation. Tuck yourself into bed and enjoy the stars or choose to black out windows using our automated shades for uninterrupted sleep.

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!

The Green Door PDX: A European Inspired Cottage.

A bolthole created from passion by Kaemingk Collection, The Green Door PDX was designed to provide a unique respite from the energy of Portland while being conveniently located only minutes from downtown and popular shopping/eating districts. We have taken queues from Europe and built a traditional field cottage tucked into the landscape at the front of the property and surrounded it with mature greenery for an inviting welcome and ultimate privacy for our guests.

Romantic Casita. HotTub and Firepit. Pets Welcome!

Come and stay in our romantic, Mediterranean Casita. This private cabin is built for singles and couples. Featuring a hot tub, fenced courtyard, fire pit, covered patio, white Linens, handmade ceramics, rustic furniture, peaceful art and off street parking. Though secluded, you're just a short walk from the vibrant Woodstock BLVD. Enjoy a unique, tranquil retreat designed for relaxation and intimacy, comfortably fitting two guests. Pet's are welcome.

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.

The Kenilworth Guest House

Showcased in the Modern Home tour of Portland, this newly built ADU is the amazing creation of Portland architect Webster Wilson. A private, airy and elegant oasis set in urban Portland. A glass house with intentional frosted glass to ensure privacy. Escape and experience the elegant grace of this unique guesthouse. Threading the needle of a city lot, the Kenilworth House lives along side a 1905 Victorian, where the host resides.

Dreamy Modern Overlook ADU

*25% off 30 days or more until May 1st* Come experience our little piece of Portland paradise! Make yourselves at home in our guesthouse, designed to feel like your home away from home. We take hosting seriously and as longtime airbnb guests ourselves, we hope to have learned a thing or two about what makes for a comfortable stay. Expect to find a spotless place with everything you need - just like home, minus the clutter!

Canopy Loft PDX

The Canopy Loft is a sun filled, second story studio designed and built by my husband and I to be a cozy home away from home. The window views are full of foliage making you feel like you're up in the trees, hence the name. Our neighborhood is quiet and calm, and we are walking distance from downtown St Johns as well as many parks. The studio can also be turned into your own personal movie theater!

ZEN HAUS. An inner SE Hawthorne/Division Studio.

LOCATION and COMFORT. Zen Haus is an easy walk to the best shops, pubs, restaurants and amenities on Hawthorne and Division's "restaurant row." This detached, self-contained studio is thoughtfully designed and furnished to satisfy your desire for comfort, convenience, calm and glorious slumber. Designed to accommodate both the holiday or business traveler, find your zen in Zen Haus.