Holiday houses in Pearl District

Chic Retreat in the Pearl

Welcome to our quiet oasis in the heart of the Central Pearl District. Nestled in one of Portland's most sought-after neighborhoods, the quiet and private studio is ideal for work or rest. Shopping, dining, & entertainment are all within walking distance. Steps to public transport for trips downtown or the NW District. A private garage is available for those with cars (extra fee) to explore city treasures like Washington Park, Forest Park, or urban events downtown or at the Moda Center.

Location · Bathroom · Nearby

Cozy artist's bungalow steps from NW 23rd

Designed for comfort by 10-year Superhosts, this 1+ bedroom single-level bungalow is recently renovated, filled with original art and period furnishings, and steps away from Portland’s beloved 23rd Ave. Stroll the quiet, tree-lined streets to the best restaurants, shops, bars and coffee, or hop the streetcar to the Pearl or downtown. Home includes a large gourmet kitchen, off-street parking, and a covered deck overlooking a cottage garden certified as a Backyard Bird Sanctuary.

Family · Location · Getting around

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.

Location · Value · Checkout

The Green Door PDX: A European Inspired Cottage.

A bolthole created from passion by Kaemingk Collection, 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.

Value · Family · Cleanliness

Melrose Place

Light, bright, and airy modern corner townhouse with an abundance of windows looking out to a quiet maple tree lined street. Freshly remodeled house with no detail overlooked. Cook in the Chef’s kitchen or eat out at the numerous restaurants and food carts within blocks of the house. Forest park and hiking trails are just a couple blocks up the street! The house is a great spot to work from home, relax, cook and serve as your home base to see the best of Portland!

Family · Location · Bathroom

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.

Location · Family · View

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

✨ Sunlit Suite Steps from NW 23rd Shopping & Dining ✨ 🌳 Timeless charm meets modern comfort in Portland's best neighborhood 🛏️ Cozy queen bed + plush sofa for two 🍳 Full kitchen with stove, oven & microwave 🛋️ Smart TV, fast WiFi & dedicated workspace 🐾 Pet-friendly — bring your furry friend ❄️ AC & heating for year-round comfort 🔒 Private entrance — entirely yours 🍽️ Steps from boutique shops, top restaurants & tree-lined streets.

Value · Family · TV

1BR - Boutique Flat - Prime NW Location

✨ Stylish NW 23rd Apartment — Portland's Best Block ✨ 🏙️ Steps from NW 23rd's top restaurants & shops 🛏️ Queen bed in private 1BR/1BA 🍳 Full kitchen with stove, microwave & coffee maker 🛋️ Smart TV & fast WiFi for streaming 💻 Laptop-friendly workspace for remote work 🌿 Private patio & entrance — your own oasis 🐾 Pet-friendly — bring your furry friend ❄️ AC & heating for year-round comfort 🍽️ Heart of walkable Northwest Portland.

Value · Location · Access

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.

Location · Value · Outdoor spaces

Old Portland Charmer

Nestled in one of Portland's most desirable neighborhoods, this charming home beautifully combines the character of the early 1900s with modern style and amenities. Walk to some of Portland's best restaurants, shops, and attractions just a short walk away. The completely remodeled home features a spacious backyard, abundant natural light, and the added convenience of off-street parking— simple luxuries that make all the difference.

Value · Family · Decor

Nob Hill Nook

Tucked behind 126-year-old Victorians in the heart of Nob Hill, this quiet ground-floor flat puts Portland’s best within walking distance. Full kitchen, queen bedroom with memory foam, pullout queen sofa, convertible twin chair, 55” TV, fast wifi, and a table that seats six. A quick walk to NW 23rd, NW 21st, Slabtown, Nob Hill, and just over a walkable mile, the Pearl District, and entry to Forest Park walking trails.

Location · Family · Condition

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!

Family · Location · View