Holiday rentals in Pearl District, Portland

Guest house in Northeast Portland

5 out of 5 average rating, 122 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.

Guest house in North Portland

4.99 out of 5 average rating, 506 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

4.95 out of 5 average rating, 533 reviews

Flat in North Portland

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.

Guest house in Northwest Portland

4.95 out of 5 average rating, 151 reviews

Queen Anne Guest Apt. In Historic District

Enjoy this private guest apartment on the bottom floor of our historic four story home. Located footsteps from Portland's best restaurants, shops, and our beloved Timbers and Thorns soccer stadium, you'll be central of NW 21st/23rd commercial districts, the Pearl district and downtown Portland. Whether traveling to visit loved ones, see a show, a game or enjoy some culinary maximalism, this is your hotel like home away from home. Business travelers will also love this central location.

Superhost

4.73 out of 5 average rating, 408 reviews

The Etoile Suite - Nob Architecture and Boutiques

Situated in the bustling and vibrant neighborhood of Slabtown in NW Portland, this conveniently located home places you just steps away from the city's best restaurants, bars, and shops. With so much to see and do in this trendy and exciting area, you'll want to extend your trip just to fully explore all the neighborhood has to offer. Whether you're a foodie, a shopaholic, or simply looking to experience Portland's vibrant nightlife, this is the perfect location for you.

Guest suite in Northwest Portland

4.92 out of 5 average rating, 103 reviews

NW Portland Oasis walkable to DT Shops & Dining

A true one of a kind stay in newly remodeled Victorian home in NW Portland. This home was established in 1890. Your MCM inspired oasis has been updated with modern touches while maintaining its original charm. Boasting a walking score of 98, it is the perfect place to come relax after a walk to countless shops and restaurants. Nestled in the Alphabet District, this city oasis straddles Downtown Portland, the Pearl District and the infamous NW 21st and 23rd ave.

Guest house in North Portland

4.94 out of 5 average rating, 212 reviews

The Solo Traveler's Backyard Garden Studio

If you are traveling by yourself, please read all the information in the listing to be sure this place is a good fit for you. The studio is located in the corner of the fully fenced and landscaped backyard of my 1910 house. The space is small, about 240 square feet. Public transportation is nearby, including 2 bus stops within 5 minute walks and the MAX train about a 15 minute walk. Several restaurants and food carts are also walking distance.

Guest suite in Northwest Portland

4.92 out of 5 average rating, 380 reviews

Large Studio in Historic Isam White House

Super Clean third floor suite in the historic Isam White House. Includes bed area, living and dining area, kitchenette with microwave, hot water kettle, dishes and small fridge and private bathroom with tub/shower. This is 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!

4.93 out of 5 average rating, 118 reviews

Spacious 1BR next to NW 23rd Ave.

Steps away from NW 23rd St, this is a 700 sq. ft., 1 BD/1BA on the 3rd floor of a 1910 craftsman. If you're looking for a great location, you have found the place. Lots of space on the 3rd floor to hang out, work, cook, etc. Fast wifi, easy street parking, plus restaurants and shops galore. Whether it's your first or fiftieth visit to Portland, this rental has all you need for a fun and comfortable stay.

Guest suite in Northeast Portland

4.93 out of 5 average rating, 285 reviews

Spacious NE Suite with Garden Access

Discover classic Portland charm in a renovated Victorian with a private, bright lower level apartment. Enjoy a spacious bedroom, modern bath, and tall ceilings. Enter through a lush garden and relax in the shared backyard. Walk to the Convention Center, Downtown, and lively neighborhoods. High-speed wifi (up to 400mbps) makes it ideal for work or leisure-a perfect home base for your Portland adventure!

4.92 out of 5 average rating, 186 reviews

Cozy Nob Hill Apartment

Enjoy your freshly renovated and furnished private apartment in NW Portland! Stay in a beautiful peaceful neighborhood. Restaurants, shops, parks, city hikes are also steps away! Comfy one bedroom, with a stocked full kitchen, and a cozy living room to hang out. the sleeper sofa can be converted to host additional guests! discount pricing for stays that are 7 days or longer!

4.96 out of 5 average rating, 112 reviews

Flat in Pearl

Free Parking/Gym/Rooftop/Pearl District/Downtown

Tahitian, one of the four types of Pearls in the world. Welcome to Pearl District in PDX! Simple yet elegant, the Tahitian Stay combines convenience and style. Location is extremely walkable and offers quick access to Whole Foods and the MAX Light Rail. Simply step out of the building and get lost in the brewery blocks, fine dining, entertainment & premier retail shopping.

Holiday rentals for every style

Get the amount of space that is right for you

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Spaces that are more than just a place to sleep

Popular amenities for Pearl District, Portland holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Pearl District, Portland's top sights

Moda Center28 locals recommend

Powell's City of Books177 locals recommend

Portland Art Museum86 locals recommend

Portland Saturday Market61 locals recommend

Lan Su Chinese Garden52 locals recommend

Providence Park32 locals recommend

Other great holiday rentals in Pearl District, Portland

5 out of 5 average rating, 7 reviews

Townhouse in Buckman

Clean, Modern Townhouse w/ Patio in walkable area

DylanRating, 5 stars3 weeks ago

Amazing hidden gem off of Burnside with lots of restaurants in the area would suggest to anyone looking for a nice relaxing trip. will definitely be staying back here next time I’m in Portland. great hosts and nice and luxury.

Flat in Portland Downtown

5 out of 5 average rating, 6 reviews

The PDX

RicardoRating, 5 stars2 weeks ago

Esteban’s place in downtown Portland was perfect—clean, stylish, and super walkable to everything. Great host, easy check-in, and the space felt like home. Highly recommend for a comfy city stay!

Apartment in Northwest Portland

5 out of 5 average rating, 23 reviews

Northwest Nob Hill! Free Parking! Walk to it all!

KathyRating, 5 stars1 month ago

Becky’s place was a beautiful place to stay on our trip to Portland. It’s a fantastic walkable neighborhood with many restaurants and eclectic shops. It’s an easy walk to a nearby New Seasons to pick up groceries and supplies. There is a cute trellis area in front of the apartment where we enjoyed sitting outside in the warm spring weather. Becky is very friendly and responsive to any needs. It was a lovely and comfortable place to stay for 11 days.

4.96 out of 5 average rating, 337 reviews

Private room in Buckman

Victorian Parlor Room. Permit# 24ASTR-PER-00491

HeatherRating, 5 stars1 day ago

I had a great stay here! The aesthetic is cozy and the atmosphere is quiet. All of Melanie’s instructions were clear. She is also super nice and accommodating. I asked her if she had any books I could borrow and she brought up a stack to pick from :). I was there for a short but busy time and I appreciated feeling relaxed in her home. Plenty of things walkable. Checked out a few restaurants/bars plus the cemetery nearby. Was able to walk to get some light groceries. Thanks Melanie!

Apartment in Northwest Portland

4.7 out of 5 average rating, 20 reviews

Nob Hill 2BR | Central Location | Washer/Dryer

LindaRating, 5 stars1 month ago

It was beautiful and comfortable.

4.54 out of 5 average rating, 13 reviews

Amusing APT in NW Portland

MatthewRating, 5 stars4 weeks ago

The property was exactly what we were expecting, very comfortable and exactly what we were looking for. The host was very friendly and quick to communicate and eager to meet and exceed expectations. Very happy with our stay

Guest house in Southwest Portland

4.98 out of 5 average rating, 44 reviews

Casetta

AlexaRating, 5 stars2 weeks ago

Jonathan's place was the perfect oasis for our Portland trip. Beautiful, luxurious, and convenient with thoughtful touches throughout. It's worth noting that the guest house is situated close to the main house and the family's office, so you'll be sharing the outdoor space. However, we found there was still plenty of privacy and the family were very respectful of our space. We'd highly recommend this space for a friendly and relaxed getaway and would love to return in the future!