Holiday houses in Pearl District

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.

Magnificent finishes and views!

A rare opportunity to get to stay in Portland's most coveted view neighborhood, full of multi-million dollar homes, and under 200 feet away from the house with the highest listing price in Portland (at $7mil). This is an every surface touched renovation in 2023/2024, utilizing Italian tile, Oregon black walnut, rare mid-century modern furniture pieces and decades old original works of art. We renovated this space in the vision of the finest boutique hotels we have stayed at throughout Europe.

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

Chic Belmont retreat w/tree views & king bed!

Experience weird and wonderful SE Portland from a serene, newly-built home in a walkable/bikeable neighborhood with king bed and lots of light! Wake up well rested and open curtain on floor to ceiling windows to morning light. Enjoy the full kitchen & soaker tub in a breathtaking architect-designed home perfect for foodies, couples, and remote work. Great location just steps from bakeries, shops, parks and taprooms. Discover the quirky character and trendy eats of Belmont-Hawthorne-Tabor!

Historic Nob Hill 2BR | Prime Walkable Spot

✨ Modern NW Portland Apartment Near 23rd Ave ✨ 🏡 Private entrance — no shared spaces 🛏️ 2 bedrooms, 2 full baths, sleeps 4 🍳 Kitchen with stove/oven, coffee & basic cookware (no microwave) 🛋️ Cable TV, fast WiFi & laptop workspace 🌿 Private patio or balcony ❄️ AC & heating for year-round comfort 🐾 Pet friendly & family friendly with Pack ’n Play available by advance request (not stored onsite) 🍽️ Walk to NW 23rd shops, restaurants & cafes. Free street parking available.

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.

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.

Aqua Star – Iconic Floating Home on the Columbia

✨ Aqua Star — Iconic Floating Home on the Columbia River ✨ 🌊 Waterfront sanctuary with panoramic river views 🛏️ 2 bedrooms, 2.5 baths, sleeps 7 🍳 Full kitchen with coffee maker (*Dishwasher currently awaiting part for repair - unavailable for use - April 2026) 🛋️ Cable TV, fast WiFi & workspace 🌅 Private deck ❄️ AC & ceiling fans for comfort 🔒 Entire floating home — all yours 📍 Northeast Marine Drive waterfront. Free parking on-site.

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.

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.

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.

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.