Holiday houses in Pearl District

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Top-rated holiday rentals in Pearl District

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Top Guest favourite
Apartment in Northwest Portland
4.96 out of 5 average rating, 492 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.

Top Guest favourite
The living room features a soft grey couch and two green armchairs arranged around a circular area rug with a blue pattern. A modern TV is positioned on a dark console. Light-colored brick walls provide a bright backdrop, enhancing the spacious feel of the area.
Guest suite in Northwest Portland
4.93 out of 5 average rating, 137 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 favourite
Home in Northwest Portland
4.8 out of 5 average rating, 338 reviews

1906 3BR Retreat • NW 23rd Boutiques & Eats

Nestled in one of Portland's most desirable neighborhoods, this elegant home has been thoughtfully refurbished to blend its original charm with modern amenities seamlessly. Originally built for the World's Fair hosted by Portland at the turn of the century, this home exudes all the old-world charm you can imagine. Step out the door, and you'll find top-rated bars and shopping just blocks away, ensuring you never have to stray far for a fantastic experience.

Top Guest favourite
The historic four-story home is presented in a charming green exterior with intricate detailing. Tall trees and colorful shrubs frame the front yard, while a decorative fence surrounds the property. Large windows and a welcoming porch are visible, showcasing the architectural character of the residence.
Guesthouse in Northwest Portland
4.94 out of 5 average rating, 203 reviews

Queen Anne Guest Apt. In Historic District

Discover a charming guesthouse apartment in the heart of Portland! This private retreat, nestled in a historic home, offers easy access to the city's vibrant scene. Explore the nearby NW 21st/23rd commercial districts, the Pearl District, and downtown Portland. Enjoy delicious dining, unique shops, and exciting entertainment, including the Timbers and Thorns soccer stadium. Perfect for leisure or business travelers seeking a comfortable and convenient stay.

Superhost
Apartment in Pearl District
4.85 out of 5 average rating, 227 reviews

Portland's Finest - Luxury Pearl District 4 BR

✨ Luxury 4BR Pearl District Retreat — Sleeps 8 ✨ 🌆 WalkScore 96 — steps to top dining & nightlife 🛏️ 4 bedrooms, 2 full baths, sleeps 8 🍳 Full chef's kitchen with dishwasher & wine glasses 🛋️ Smart TV, fast WiFi & dedicated workspace 🐾 Pet-friendly with private entrance & patio ❄️ AC & heating for year-round comfort 🔒 Entire home, washer/dryer, crib available 🌲 Minutes to Forest Park trails & Pearl District shops. Free street parking.

Top Guest favourite
Home in Northwest Portland
4.96 out of 5 average rating, 138 reviews

Luxury Living on NW 23rd Ave, Walk Score 99

✨ Luxury 4BR in Heart of NW 23rd ✨ 🏠 Fully renovated 2000 sq ft home 🛏️ 4 bedrooms, 5 beds — sleeps 12 🍳 Chef's kitchen with stainless steel appliances 🛋️ Spacious dining & living areas 💻 Fast WiFi & laptop-friendly workspaces 🌿 Private patio with outdoor seating ❄️ AC & heating for year-round comfort 🔒 Entire home with private entrance & garage 📍 Walk Score 99 — steps from Salt & Straw, shops & top restaurants. Free garage parking.

Top Guest favourite
An open living space features a stylish wooden staircase, enhancing the flow of natural light. A modern dining table is accompanied by Arne Jacobsen Ant dining chairs. Decorative plants and a round mirror add a touch of elegance, while large glass doors provide a view of the outdoor area.
Home in Portland
4.99 out of 5 average rating, 463 reviews

Modern Guesthouse in Portland's Central Eastside

Tall ceilings, an open staircase and walls of windows flood the space with light (even in Portland), while molded plywood Eames chairs add mid-century style. Located in the heart of Portland within walking distance to great restaurants, coffee and parks. Fast, gigabit fiber internet, full kitchen, large table, and private outdoor spaces help maximize your stay and comfort, whether you're alone or with a group. Editor's pick in Dwell.

Top Guest favourite
The historic Isam White House features a striking blue exterior with intricate details and large windows. Lush greenery surrounds the property, complemented by seasonal foliage. The well-maintained garden is enclosed by a decorative black iron fence, adding to the home's charm.
Guest suite in Northwest Portland
4.92 out of 5 average rating, 443 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!

Top Guest favourite
The historic Firehouse No. 17 features a striking brick facade with red detailing and elegant windows. Two large garage doors are framed by decorative patterns, creating an inviting entrance. The building's architectural elements reflect its storied past, surrounded by manicured greenery.
Guest suite in Northwest Portland
4.96 out of 5 average rating, 104 reviews

Historic NW Nob Hill Firehouse No. 17

Firehouse No. 17 is a unique and interesting place to stay. The engine bays of the Firehouse have been converted into a beautiful and spacious living area. There are historic photos of the Firehouse that help tell its story from a working firehouse to a fabulous residence. Please come experience this historic firehouse, located in NW Portland. It is an easy walk to bustling NW 23rd restaurants and shops.

Superhost
Apartment in Northwest Portland
4.73 out of 5 average rating, 486 reviews

Bright & Stylish Alphabet District Suite | NW 23rd

✨ Sun-Drenched 1BR in Portland's Alphabet District ✨ ☀️ Gorgeous natural light & oversized windows 🛏️ Cozy queen bed with premium linens 🍳 Full kitchen with gas range & dining table 💻 Laptop-friendly workspace with fast WiFi ❄️ AC & heating for year-round comfort 🐾 Pet-friendly — bring your furry friend 🚶 Steps to NW 23rd boutiques, cafes & Forest Park. Metered street parking.

Top Guest favourite
A modern kitchen features sleek black appliances and white cabinetry. Pendant lights hang over the counter, illuminating the stylish backsplash. Counter space is complemented by a sink and a coffee maker, creating a functional cooking area in a welcoming atmosphere.
Apartment in Northwest Portland
4.93 out of 5 average rating, 228 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!

Top Guest favourite
A spacious window offers a view of distant hills covered in greenery and autumn colors. A cozy chair sits nearby, creating a comfortable spot to enjoy the scenery. The room is softly illuminated, enhancing the serene ambiance while allowing natural light to flow in.
Apartment in Pearl District
4.96 out of 5 average rating, 152 reviews

Free Parking/Gym/Rooftop/Pearl District/Downtown

Akoya, one of the four types of Pearls in the world. Welcome to Pearl District in PDX! Simple yet elegant, the Akoya 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.

Popular amenities for Pearl District holiday rentals

Quick stats about holiday rentals in Pearl District

  • Total holiday rentals

    Explore 120 holiday rentals in Pearl District

  • Nightly prices starting at

    Pearl District holiday rentals start at $84 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,330 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 60 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Pearl District holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Pearl District rentals

  • 4.8 Average rating

    Pearl District stays are highly rated by guests—averaging 4.8 out of 5!

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