Vacation rentals in Pearl District

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Top-rated vacation rentals in Pearl District

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

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Top guest favorite
The exterior of a two-story studio is framed by lush greenery and trees. The building features a spiral staircase leading to a private balcony with black railings. A shared garden area is visible below, with a hammock and various plants around the space.
Guesthouse in Piedmont
4.98 out of 5 average rating, 226 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.

Top guest favorite
The exterior of the home is highlighted by contemporary design elements and a clean white facade. A flowering tree adds a touch of color, while large glass doors invite natural light into the living area. Surrounding landscaping is thoughtfully arranged with minimalistic plantings.
Guesthouse in Arbor Lodge
4.99 out of 5 average rating, 532 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

Guest favorite
An open bedroom features a spacious bed with a light blue quilt and matching accent pillows. A textured wall art piece is displayed above the headboard. Natural light illuminates the neutral-toned carpet, complemented by a small wooden nightstand and a mirror reflecting the inviting space.
Guesthouse in Portland
4.94 out of 5 average rating, 172 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.

Top guest favorite
A workspace is positioned by large windows, allowing natural light to fill the area. A stylish desk with a lamp is accompanied by white chairs. The room features warm wooden flooring and modern furnishings, contributing to a comfortable environment for work or relaxation.
Apartment in Northwest District
4.96 out of 5 average rating, 458 reviews

Pet Friendly NW Nob Hill High End Private Apt.

Beautiful high end modern private apartment built in a historic 1904 Craftsman in Nob Hill. Walk two blocks to NW 23rd for a wide variety of stellar restaurants and shopping or take a 10min walk to get to the heart of the city or to the famous trails of forest park. Easy access to transportation all over the city just steps away. View Mt. Hood from the front porch or relax with your own large private yard and let your pets run. Listed on VRBO 395585, excellent reviews.

Guest favorite
A bright bedroom features a spacious bed with a colorful floral quilt and blue accent pillows. Natural light enters through a large window, illuminating the room. A nightstand with a lamp stands next to the bed, and a wooden bench is placed against the wall.
Guest suite in Portland
4.92 out of 5 average rating, 148 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!

Guest favorite
Apartment in Northwest District
4.84 out of 5 average rating, 338 reviews

NW 23rd - 1BR - Best Location - Historic Beauty

Flooded with natural light, this stylish suite blends timeless charm with modern comfort in one of Portland’s best neighborhoods. Nestled just off NW 23rd Ave, enjoy boutique shopping, top-rated restaurants, and tree-lined strolls right outside your door. Inside, you’ll find a curated living space with a plush sofa, full kitchen, fast WiFi, smart TV, and comfy queen bed—perfect for cozy nights in or recharging after a day exploring the city.

Top guest favorite
A warm sleeping area features a spacious bed framed by two wooden nightstands with lamps. A bright yellow throw blanket lays across the bed. The walls are painted a deep teal, and natural light enters through a window with a beige shade. A decorative piece on the wall adds character.
Guesthouse in Sullivan's Gulch
5 out of 5 average rating, 439 reviews

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.

Top guest favorite
The exterior of a guesthouse is shown, featuring a charming wooden facade and large windows. A private outdoor patio is surrounded by lush greenery, including vibrant plants like a red maple and bamboo. A small round table with wooden chairs invites outdoor relaxation.
Guesthouse in Overlook
5 out of 5 average rating, 317 reviews

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.

Top guest favorite
A bright living space is highlighted by sloped ceilings and skylights. A comfortable sofa and armchair are arranged near a coffee table, with a dining area featuring white chairs in the background. The kitchen is partially visible, enhancing the open layout.
Apartment in Portland
4.94 out of 5 average rating, 133 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.

Top guest favorite
A charming Victorian home with a colorful shingle facade and a welcoming front porch. The surroundings include a garden with lush greenery and vibrant flowers, enhancing the inviting entrance. Clear skies offer a bright backdrop to this classic Portland residence.
Guest suite in Eliot
4.93 out of 5 average rating, 303 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!

Top guest favorite
A spacious studio apartment features a cozy sleeping area with a wooden bed frame and soft bedding. A dining table with chairs is nearby, along with a comfortable sofa. Large windows allow natural light, and entertainment options include a flat-screen TV. Kitchen appliances are neatly arranged along one wall.
Guesthouse in Buckman
4.98 out of 5 average rating, 883 reviews

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.

Guest favorite
Apartment in Northwest District
4.84 out of 5 average rating, 290 reviews

Bright 1BR - Walk to Coffee, Food & Shopping

This bright and stylish one-bedroom apartment is located in one of Portland’s most walkable and desirable neighborhoods. Just steps from NW 23rd Avenue, you’ll have the city’s best restaurants, shops, and cafés right outside your door. Inside, enjoy a thoughtfully furnished space with a queen bed, Smart TV, fast WiFi, and a full kitchen - ideal for cozy nights in or urban adventures.

Popular amenities for Pearl District, Portland vacation rentals

When is the best time to visit Pearl District?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR1,720 ZARR1,720 ZARR1,824 ZARR1,876 ZARR1,841 ZARR1,893 ZARR2,067 ZARR1,928 ZARR1,789 ZARR1,911 ZARR1,789 ZARR1,720 ZAR
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Quick stats about vacation rentals in Pearl District

  • Total vacation rentals

    Explore 110 vacation rentals in Pearl District

  • Nightly prices starting at

    Pearl District vacation rentals start at R869 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 2,500 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    110 of Pearl District vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Pearl District rentals

  • 4.7 Average rating

    Pearl District stays receive an average rating of 4.7 out of 5 from guests

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