Holiday rentals in Portland

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Top-rated holiday rentals in Portland

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Top guest favourite

Guest suite in Richmond

4.98 out of 5 average rating, 381 reviews

Walk to Se Division from a Sleek, Architect Designed Space

My wife, Raechel, and I originally designed and built this ADU ( accessory dwelling unit ) with the intention of living there full time, but due to a change of plans, it's available to you. The space was designed by Buckenmeyer Architecture, and was constructed by me. Our space features many unique elements such as: paper-composite counter tops and bathroom tiles, real copper backsplash and bathroom walls, polished concrete floors, cedar tongue and groove ceiling, burnt cedar siding, 16' multi-slide window wall (please open and close slowly), moveable cedar slat screens, custom frosted glass pocket doors, and custom apple-ply kitchen cabinets by George Ramos We love to cook and put great effort into getting the kitchen space dialed in. The kitchen features: bosch speed oven (microwave and convection oven), bosch dishwasher, 2 burner gas range, and Pull-out exhaust and lighting We hope you enjoy the space and neighborhood as much as we do! The guesthouse has it's own separate entrance with a smart lock for convenient self check in. You'll receive the unique code prior to check in. We live in the main house and are available to help make your stay as great as possible. We value your privacy and will not stop by unless contacted. Please text for the quickest response. Nearby Division Steet is known as restaurant row and features some of the best food in Portland, including Pok Pok, Salt and Straw, and Ava Genes. On a warm summer night, there will be hundreds of people just going for a stroll up and down Division. Our guesthouse is a 2 minute walk from a major bus stop, and a Biketown stall where you can rent a bike by the trip. There is no dedicated parking space but there is an abundant amount of non-metered unlimited on-street parking directly in front of our guest house on 28th pl. The Roku Tv enables you to login to your entertainment provider of choice, please remember to logout. The Bose Soundbar is wired to output the TV's audio, but can also be connected to via bluetooth by hitting the bluetooth icon on the Bose remote and pairing with your device. We provide locally roasted coffee beans, a manual conical burr grinder, insulated french press, stovetop kettle, and creamer + sugar. Please enjoy the in-shell Hazelnuts!

Top guest favourite

Guest suite in Cully

4.95 out of 5 average rating, 144 reviews

Portland Nest Guesthouse

Your urban forest oasis awaits you at the Nest Guest House! This newly constructed, well appointed and restful apartment has all you need for a perfectly Portland getaway. Wake up to birdsong, coffee/tea and snacks. Enjoy the outdoor space, garden views, and relax in luxurious comfort in your 730 sq. feet apt. Very close to the airport, short walk to restaurants, food carts, grocery store and transit. Nearby neighborhoods (10 min.drive/20 min walk) Fremont St, Alberta Arts, 42nd St, Hollywood.

Top guest favourite

Guest house in Boise

5 out of 5 average rating, 121 reviews

Cedar House

Nestled in inner North/NE Portland, this cozy guest house sits between the vibrant Mississippi and Williams shopping districts and is just a short day trip to lovely hikes in the surrounding area. We're a quick bus ride from the center of town and a short walk to a wide variety of local shops and dining. High ceilings and plenty of natural light give this intimate space an airy, open feeling, making it an in-town sanctuary with easy access to public transport, bike lanes, and on-street parking.

Top guest favourite

Guest house in Kenton

4.99 out of 5 average rating, 505 reviews

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

Top guest favourite

Flat in Overlook

4.96 out of 5 average rating, 532 reviews

Close-in, private Overlook retreat.

The Overlook neighborhood is one of Portland's hidden gems. Quiet, tree lined, yet only a few minutes from all the action Portland serves up. Walk or ride to meals, brewpubs or shopping in the Mississippi and Williams districts. Hop a train (three blocks away) to downtown or The Pearl District. Or to unwind, walk to Overlook or Mocks Crest parks for sweeping views of downtown Portland, Forest Park and the Willamette River. Please read on to see if this space is the right fit for you.

Top guest favourite

Guest house in Woodlawn

4.99 out of 5 average rating, 245 reviews

Sorta Summer House w/ sauna & outdoor shower

The guesthouse is a private oasis in the city. It's surrounded by fruit trees and tall Chinese Mountain bamboo. It's a quick walk to Woodlawn Park, great coffee, a bakery, pizza, whiskey bar, a brewery, seasonal farmers market, and minutes from Alberta Arts District. The airy, open floor plan is filled with natural light, mixed textiles and warm woods. A cedar-surround outdoor shower and private 5x7 Finnish sauna lend to the spa-like setting. Guests say it’s hard to leave!

Top guest favourite

Guest suite in Kenton

4.94 out of 5 average rating, 326 reviews

Modern Guesthouse in Kenton

Private, modern guesthouse in the Historic Kenton neighborhood in North Portland. Walk 1/2 a block to Kenton Park and a few blocks to the Kenton business district with great shops and restaurants. The apartment offers light and bright interior with touches of Scandinavian design. Open floor plan from kitchen to living room. One bedroom, one bath, plus a full size sleeper couch. Free street parking in front. Do not park in the driveway please. 15-20 min to downtown.

Top guest favourite

Tiny home in Montavilla

4.98 out of 5 average rating, 428 reviews

The Monta-Villa Garden Cottage — cats + chickens

Your cottage is private with views of the garden. It’s a unique tiny home that feels big with high ceilings, lots of natural light & warm accents. You have everything to cook most meals. There are plenty of local food, drink & shopping options nearby. Walk the neighborhood, see city highlights, visit parks, hike to falls, feed chickens, pick seasonal fruits & veggies, or just sit in the garden or covered patio with a book & a cat. This is your home away from home.

Guest favourite

Guest suite in King

4.94 out of 5 average rating, 390 reviews

NE Portland Private Entry Studio-Walking Distance

1 block off of NE Williams avenue: A cool and trendy place to soak up your authentic Portland experience! Coffee shops, the BEST restaurants around, Bars, workout studios, shopping, CoCo Donuts and more. Studio space includes private separate entrance, backyard patio for your using, Kitchen (Fridge/freezer, toaster, microwave), en suite bathroom with shower, queen size bed, and large flat screen TV. WIFI included. Happy to give recommendations for a good time!

Top guest favourite

Flat in Kerns

4.97 out of 5 average rating, 297 reviews

Studio in Walkable Foodie Heaven

We're on a quiet side street – right around the corner from a dynamic restaurant scene in Kerns, the 5th coolest neighborhood in the world. Stroll to parks, live music, vintage shops, and a vintage movie theater. Walk, Lyft/Uber, bicycle, or use Portland’s amazing public transportation everywhere. Tall windows overlook greenery and a cozy porch. Our family's 1900 house has been divided into separate apartments. Its like an artsy hotel room, but much more homey!

Top guest favourite

Guest house in Overlook

4.97 out of 5 average rating, 393 reviews

The Green Door PDX: A European Inspired Cottage.

A bolthole created from passion by Kaemingk Design, 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.

Guest favourite

Guest suite in Portland

4.93 out of 5 average rating, 127 reviews

One bedroom suite in historic Isam White House

Clean third floor one bedroom suite in the historic Isam White House with bedroom, living area with convertible sofa, dining area, kitchenette and private bathroom with shower. Includes access to 3rd floor private balcony (furniture removed in fall / winter) . One of the last grand mansions downtown that hasn't been converted to condos or offices. We are at the shopping and restaurant districts of Northwest 21st and 23rd Avenues. Walkability score of 97!