Guest house holiday rentals in Portland

Peaceful Loft - Close to shops, Train & Downtown

Our peaceful detached apartment is located in Irvington, a beautiful historical neighborhood 7 minutes from downtown. You would not need a car as you can walk to the MAX train station. We furnished our space with a comfortable brand new king size bed and full size sleeper sofa. Bedding & duvet cover washed every time. The decoration is tropical inspired art and from Hawaii. There is a cute and equipped kitchenette with coffee maker, tea make, microwave, dishwasher electric range for small meals.

Woodstock Tiny House

Detached, very small (300 sq ft) guest house in the Southeast Portland neighborhood of Woodstock. Lots of walkable eateries as well as New Seasons and Safeway within a 5 minute walk. Close to Reed College, Woodstock Village, Springwater Trail, Southeast Portland Neighborhoods, Public Transportation. You’ll love the location, the outdoors space, and the ambiance. Good for couples, solo adventurers, and business travelers. TV (Netflix enabled!), A/C (summer months), heat, coffee, fridge/freezer.

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.

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 Salt & Straw, Loretta Jean’s, Insomnia Cookies, New Cascadia (gf bakery) Oma’s Hideaway, Cibo, Someday, The End, and food carts.

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.

Modern and Bright Laurelhurst Abode

Our one bedroom cottage is completely private, accessible by a separate walkway, and has an outdoor patio. Extra time was spent choosing finishes and creating a modern, comfortable, and light-filled space. You’ll find everything you need for a weekend in Portland, or a long-term stay. We’ve outfitted a full kitchen, full bathroom with luxurious tub and plush towels, a bedroom with a queen mattress and soft bedding, washer and dryer, and lots of extra touches.

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!

Colorful, spacious, light-filled guesthouse on MAX

Welcome to Juniper House! We designed our backyard guesthouse to be a bright, cozy loft, full of sunlight, exposed wood, tasteful furnishings and colorful finishes. Enjoy a private, 600-sq-ft space with an outdoor patio in a quiet, close-in Portland neighborhood, just blocks from light rail and within walking distance to a wide variety of great restaurants and watering holes. Perfect for couples and longer stays.

Cozy Portland Studio Apartment

The space is a well appointed, comfortable studio apartment. It is an ADU at the back of the main house. All the amenities that one would desire are provided (wifi, internet, cable TV, washer & dryer, fridge, dishwasher, stove, microwave, AC, cooking utensils, etc., etc). It is also very modern and clean, with a private entrance and keyless entry. Close to many restaurants, bars and coffee shops.

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!

Cozy Clinton Cottage (close-in SE off Division)

Our lovingly renovated guest cottage is detached from the main house, with a private entrance and outdoor seating area. Our central location is great for exploring all of the best that Portland has to offer, with easy access to public transit and bike routes. The space is very cozy and has everything you need for a fantastic Portland vacation or work trip.