Guesthouse holiday rentals in Portland

Pet Friendly, Cozy & Curated Designer Guesthouse

Our guesthouse is situated behind our home, located on a large corner lot in beautiful Grant Park. Surrounded by picturesque homes and tree-canopied streets, it’s a perfect combination of peace and quiet alongside accessibility. Dozens of local shops and fabulous PDX restaurants, just a 10 minute walk away. Five minutes to freeway access, guests enjoy convenient options, exclusive privacy, and detailed designer touches. A perfect base camp for an extended PNW exploration, or a weekend getaway!

Value · Location · Pets

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 · Location · Outdoor spaces

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 · Sleep quality

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 · Value · Nearby

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.

Location · Family · Sleep quality

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 · Wi-Fi

Fresh North Portland Studio

Walk to Restaurants, Coffee Shops, Bars, Shopping, Mississippi Avenue District, MAX Yellow Line, Public Library, PCC-Cascade Campus. Beautifully furnished space with a fully stocked kitchen, high ceilings, comfy bed and custom-built features like the walk-in shower and kitchen bar. Bright and open indoor/outdoor living with French doors that open to a private patio. Great for couples, solo adventurers, and business travelers. Well-behaved dogs are permitted. No cats.

Family · Location · Check-in

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.

Value · Location · Long stay

The Loft in Hawthorne Tabor

Loft style guest house with private entrance & private porch in a quiet and convenient Hawthorne Tabor neighborhood. Location: Explore the many restaurants, bars, boutiques, etc in less than 10 min walk along SE Hawthorne Blvd including: Por Que No?, Tabor Bread, New Seasons, Farmhouse Kitchen Escape to the tranquility of Mt Tabor park & trails after an enjoyable 20 min walk through West Tabor neighborhood 15 min drive to PDX Airport 15 min drive to Downtown

Location · Value · Biking

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.

Location · Value · Condition

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.

Family · Value · Biking

Handcrafted Urban Hideaway | Private Driveway

Stay in this handcrafted rustic-industrial studio featuring reclaimed wood walls, 15-foot vaulted ceilings, and thoughtful custom details throughout. Private entrance and driveway, 10-minute walk to MAX light rail, and under 25 minutes to Mississippi Ave. Enjoy high-speed WiFi, a well-appointed kitchenette, and all the comforts of home in this unique urban Portland hideaway.

Value · Family · Getting around