Guesthouse holiday rentals in Portland

Clinton St Guesthouse • Walkable & Artistic

Stylish Clinton St guesthouse steps from cafés, bakeries, and transit. Features unique hand-painted floors, local Portland art (including child artists), and a small library of Portland authors. Queen bed, blackout shades, AC, desk, fast Wi-Fi, washer/dryer, and a coffee station with Moccamaster, grinder, AeroPress, French press, pour-over, and local beans. Walk to OK Chicken, Salt & Straw, Loretta Jean’s, Cookies, New Cascadia (gf bakery) Oma’s Hideaway, Cibo, Someday, The End, and food carts.

Family · Location · Biking

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.

Family · Value · Walkability

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.

Family · Value · View

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

Value · Family · View

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!

Location · Family · Pets

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.

Family · Value · Condition

Beautiful Alberta Guesthouse | Outdoor Soaking Tub

Come & enjoy this custom-built, detached guesthouse in the famous Alberta Arts District. Our guests will find a peaceful retreat awaiting them in this open & bright, modern space featuring beautiful architecture with all the amenities one looks for during their PDX getaway. Inside, you will find a full kitchen, washer & dryer, AC, smart tv, fast wifi, a spa-like bathroom & more thoughtful touches to give you the perfect spot to rest and recharge in between your Portland adventures!

Value · Location · Accuracy

The Westmoreland Lighthouse - Private studio in SE

We've dubbed this stunning, fully detached studio the "Lighthouse" because of the way natural light pours through the 550-square-foot studio's many windows and dances off its walls and vaulted ceilings. An open loft offers soothing views. We are tucked into the Westmoreland neighborhood's quiet residential area, but are only a five minute walk from more than 20 restaurants and entertainment features. Westmoreland Park, Reed College and downtown Portland are just minutes away by car.

Location · Family · Amenities

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.

Location · Value · Air conditioning

Intimate Casita. Hot-tub, Movie Loft and Chiminea.

Our beautiful Spanish style Casita is the perfect, intimate and romantic getaway to explore Portland from. Soft white linens, handmade ceramics, rustic furniture, original artwork, tranquil outdoor area. movie loft, private courtyard with hammocks, hot tub and fire pit. The Casita is close to restaurants, bars, ice-cream parlors, famous food cart scenes, boutiques, supermarkets, dogs parks & much more. We LOVE your pets & welcome them to stay with you!

Family · Value · Sleep quality

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.

Location · Value · Cleanliness

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!

Family · Location · Quiet