Holiday rentals in Pearl District

Luxurious king bed suite! Free Garage Parking

This high-end downtown apartment on the 6th floor offers breathtaking views of the city. The apartment is furnished with modern furniture and features a spacious living area with ample natural light. Equipped with underground parking, and access to nearby restaurants, entertainment venues, and shopping areas all within walking distance, this lofts prime location make this contemporary style apartment an ideal choice for those seeking a sophisticated and comfortable urban living experience.

Close-in, private Overlook retreat.

The Overlook neighborhood is one of Portland's hidden gems. Quiet, tree lined, yet only a few minutes from all the action Portland serves up. Walk or ride to meals, brewpubs or shopping in the Mississippi and Williams districts. Hop a train (three blocks away) to all quarters. Or, to unwind, walk to Overlook or Mocks Crest parks for sweeping views of downtown Portland, Forest Park and the Willamette River. Please read on to see if the studio's lower ceiling is the right fit for you.

The Haseman House

Come stay in our Architectural micro home in NE Portland. Close to Mississippi and everything that NE Williams has to offer. Thoughtfully deigned with many amenities. A great WFH vacation retreat. This little house is located in the back of a main house. The backyard is shared with the main front house. There is only street parking but it is free and typically available. We are close to public transportation and rental bikes as well as an organic grocery store... very walkable.

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! Ten years with a consistent five star rating says it all.

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. Free street parking.

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.

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!

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.

The Loft; N. Portland

Private Loft Apartment – Designed and built by Connor 2022 Centrally located in N Portland, a few blocks from the University of Portland and easy access to the many eateries, coffee shops, and outdoor experiences that St. Johns has to offer. A true haven for visiting parents, business travelers, couples and solo travelers alike. You’ll love the aesthetic and amenities, such as a King sized Casper mattress. Pet and Smoke Free environment.

Overlook Cottage, Upscale w/ Off-Street Parking!

Be our guest in a newly completed two bedroom two bath cottage designed specifically for short term stays and complemented with designer finishes and décor. Located in Portland’s historic Overlook neighborhood; a short walk to light rail transit, Overlook Park, and Mississippi Street boutique shops and restaurants. We strive to provide a welcoming and hospitable environment with strict cleaning protocols.

1BR • Fast WiFi • Walk to Dining & Breweries

✨ Chic NW 23rd Apartment — Walkable Urban Oasis ✨ 🛏️ Queen bed in bright 1BR/1BA 🍳 Full kitchen with stove, oven & coffee bar 📺 Smart TV & fast WiFi throughout 💼 Laptop-friendly workspace for remote work 🐾 Pet-friendly — bring your furry friend ❄️ AC & heating for year-round comfort 🔒 Private entrance — entire place is yours 🍽️ Steps from NW 23rd shops, cafés & restaurants. Free street parking.

Sage Guest House

Enjoy free parking adjacent to the Guest House! Located steps from the Hawthorne District and nestled in the historic Ladd's Addition neighborhood, this guest house is near fine restaurants, coffee shops, entertainment venues, and food carts . Stroll in the shade of century old Elm trees, and discover four public rose gardens located at the compass points within this 1890 neighborhood.