Holiday rentals in Pearl District, Portland

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Top-rated holiday rentals in Pearl District, Portland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Guest house in Northeast Portland

4.98 out of 5 average rating, 113 reviews

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.

Guest favourite

Tiny home in Northeast Portland

4.98 out of 5 average rating, 634 reviews

Handcrafted Blue Door Micro-Loft in Hip and Arty Location

Discover a unique, custom-built tiny home with a big feel. The residence features an open-plan layout, a mezzanine bedroom, rustic wood finishes, industrial accents, cathedral ceilings, and access to a shared garden patio with a BBQ. Low cleaning fee & easy checkout. Close to action in fun Mississippi district, yet quiet & private. Self check-in. Close-in to downtown & Convention Ctr. As seen in “best of portland airbnb” online reviews: wheatlesswanderlust, roadaffair, & bridgesandballoons.

Guest favourite

Guest suite in Northwest Portland

4.92 out of 5 average rating, 128 reviews

♥ Cozy Nob Hill 2br, walk to Pearl and Downtown!

Clean and cozy getaway in an amazing central location. Walk just a few blocks to shopping on NW 23rd, restaurants in the Pearl, Powell's Books, the West End, Providence Park, or even Downtown. This modern 2 bedroom private basement apartment occupies a full floor of a 1907 Craftsman in the heart of the Alphabet Historic District. Features include king mattresses from Helix for a great night's sleep, a kitchenette with fridge, microwave and Nespresso maker, and original art from local artists.

Superhost

Flat in Northeast Portland

4.83 out of 5 average rating, 291 reviews

The Bohemian Spirit - Live Music, Eateries + Bars

Welcome to the heart of Mississippi St, where everything is at your doorstep! Step out of the front door and you'll find yourself in the middle of endless restaurants, coffee shops, bars, and so much more. With all these options just a few blocks away, you'll never run out of things to do. When it's time to relax, enjoy the massive 4K HDTV, cook an amazing meal in the spacious kitchen. Whether you're a solo traveler or on a romantic getaway, this is the perfect retreat in the heart of PDX.

Guest favourite

Home in Northwest Portland

4.98 out of 5 average rating, 377 reviews

★Modern Nob Hill Getaway★

Bright, spacious basement apartment located in beautiful, walkable Nob Hill. Close to many of Portland's finest coffee, donut, dining and ice cream establishments with easy public transport/Uber access to all of Portland’s great neighborhoods. This modern getaway has polished concrete floors, an open kitchen with new stainless appliances, Portland-centric decorations and everything you need to enjoy your Pacific Northwest getaway! Perfect for a couple, a couple of couples or a small family.

Guest favourite

Guest house in Central Northeast Portland

4.99 out of 5 average rating, 155 reviews

Grant Park Guest House

Newly built guesthouse in highly desirable Grant Park. Beautiful and relaxing one level space with vaulted ceilings, exposed beams, skylights and lots of natural light. All amenities: high speed internet, washer & dryer, full kitchen, memory foam mattress, TV, and private entrance with patio and cafe set. Easy check out! Location is close to everything: great restaurants, food cart pod, Whole Foods, Trader Joe's, Grant park, airport, and more! Walk score of 94. Great space for a get away!

Guest favourite

Flat in Pearl

4.99 out of 5 average rating, 221 reviews

Downtown Pearl District Upscale Apt. w/ Rooftop!

Upscale apartment with unbeatable location featuring luxury amenities including a rooftop deck with fire pit & Sky Entertainment lounge. Located in the heart of the Pearl District, you will find endless opportunities to create new memories! This famous neighborhood is a travelers top travel destinations when visiting Portland. This popular destination features art galleries & cultural institutions, as well as stylish shops, acclaimed eateries and brewpubs all within walking distance!

Guest favourite

Guest house in Northwest Portland

4.95 out of 5 average rating, 107 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.

Guest favourite

Guest suite in Northeast Portland

4.88 out of 5 average rating, 761 reviews

Mississippi SkyNest

Enjoy your own private suite in North Portland, two blocks off trendy Mississippi Ave. 5 minutes to downtown Portland, and 20 min to the airport, and shops, restaurants, breweries all within walking distance! My home has no pets at the moment and children on the main floor, but you have your own entrance and deck to create privacy and tranquility. I am so excited to share our master suite with you and offer suggestions on request for all the wonderful things Portland has to offer!

Guest favourite

Guest suite in Northeast Portland

4.97 out of 5 average rating, 1004 reviews

The Perch - Relax in style/Walkable Location!

An Architectural staircase leads to your private birds-eye deck as you enter your airy urban sanctuary. Bright, clean, elemental decor offer the perfect retreat - just one block off of fabulous Mississippi St. Restaurants, bars, shopping and entertainment venues at your doorstep! Fast Wi-Fi and extra cleaning protocols. Minutes from downtown via bike, bus, light rail or car. Easy access to/from the Airport too! Six years with a consistent five star rating says it all.

Guest favourite

Guest suite in Northwest Portland

5.0 out of 5 average rating, 109 reviews

Historic Goose Hollow Guest Suite

Relax in a historic Goose Hollow guest suite with a private entrance, free street parking , air-conditioning, and wifi. This quiet treetop suite is close to everything (walk score 92), including Washington Park (Rose Garden/ Japanese Garden), Powell’s City of Books, Portland Farmers Market, and more. Close to fabulous hiking, top-rated bars, restaurants, and shopping in Alphabet District/Nob Hill, the Pearl, and Downtown. Two blocks to Providence Park for soccer games!

Guest favourite

Guest suite in Northwest Portland

4.92 out of 5 average rating, 306 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!