Guest house holiday rentals in Portland

Spacious, bright garden studio on Peninsula Park

Explore the world-class restaurants, coffee shops and bars in the nearby Williams and Mississippi districts. Take a stroll around the award winning (and oldest) rose garden in the City of Roses across the street in Peninsula Park. At home, this second story studio has extra space in the meditation loft, a full kitchen, fast internet, and projector for streaming. Enjoy your private deck over the shared garden with hammock and H/C outdoor shower. Bus and train nearby with ample on-street parking.

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 Haseman House

Come stay in our Architectural micro home in NE Portland. Close to Mississippi and everything that NE Williams has to offer. Thoughtfully deigned with many amenities. A great WFH vacation retreat. This little house is located in the back of a main house. The backyard is shared with the main front house. There is only street parking but it is free and typically available. We are close to public transportation and rental bikes as well as an organic grocery store... very walkable.

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.

Poolhouse of Portland Architectural Gem

Private guest house adjacent to Pietro Belluschi's "Sutor House", featured in Dec 2017 Dwell Magazine. Pool-house is 750 square feet, and features a master bedroom, full bath, living area with kitchenette, and access to and shared use (With our family) of the swimming pool in summer months (June, July, August). Surrounded by private wooded garden with Japanese plantings and water features. Located in Portland's West Hills, just minutes from Downtown.

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.

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!

Creative & Clean Bungalow in Portland Hot Spot

Welcome to The ArtHaus. Soak up the sun on the patio of this creatively crafted home. Inside, polished concrete floors combine with classic finishes and attention to detail, including a sliding timber door. Vibrant color pops abound, not least from the original artworks. Accepting guests and implementing extra cleaning protocols. Excellent wireless internet speeds!

Private Arbor Lodge Cottage

Architect designed Arbor Lodge cottage. Located in a quiet neighborhood 1/2 block from Arbor Lodge Park. The space is bright and gets a lot of natural light. I hope you find it comfortable and relaxing. It is also conveniently located to many nearby shops, grocery store, restaurants, pubs and transit connections (light rail and bus).

Hawthorne Wisteria Retreat

A private studio in a garden courtyard located in the heart of bustling Hawthorne and Division neighborhoods, this retreat offers walking access to countless top restaurants, boutiques, vintage stores, book stores independent movie theaters and more. There is ample street parking right infront of the house or very near.