House holiday rentals in Portland Downtown

The Jacobberger House Portland's Historic 5 star

Discover the abundance of old world charm and architecture in this beautifully restored Craftsman home. Built in 1904 by Joseph Jacobberger, this home is perched on the hill with stunning city & mountain views. This extra spacious 3500 sq foot 5 bed hillside paradise awaits you. GIGABIT WIFI with NETFLIX included. A central location with easy access to beach, mountains, and wineries. A great place to make memories with friends or family. All rooms passed safety Inspection & B&B licensed.

Value · Family · Quiet

Historic Charm • Modern Comfort • Spacious • 3BR

✨ Remodeled 3BR Near Mississippi Ave & Williams ✨ 🏡 Private home with classic charm & modern updates 🛏️ 3 bedrooms, 1.5 baths — sleeps 6 🍳 Fully equipped kitchen with dishwasher & coffee maker 🛋️ Stylish living spaces with Smart TV & fast WiFi 💻 Laptop-friendly workspace for remote work 🌿 Private backyard & patio for relaxing ❄️ AC & heating for year-round comfort 🐾 Pet-friendly with private entrance — entire place yours 🍽️ Walk to Mississippi Ave, Williams & OX. Free street parking.

Location · Value · Air conditioning

Modern Home — Prime Alberta Arts

This new home is steps from lively Alberta Street, the heart of NE Portland. It's perfect for couples, business travelers, and anyone looking to explore Northeast, Portland's best neighborhood. Plush king-size bed, open kitchen and living room, 1.5 bathrooms, and private yard. Explore awesome restaurants, bars, and shops around the corner, while staying on a quiet residential street. This home is just 15 minutes from the airport, and close to downtown (transit friendly!). Hablamos español.

Location · Value · Layout

The Clinton Modern

The Clinton Modern is a clean and contemporary accommodation located in the heart of the famed Clinton/Division neighborhood in Portland, OR. The neighborhood is itself embedded in the equally renown East Portland district, known for its dynamic food, rich cultural offerings, and quirky nightlife. The locale is quiet yet conveniently accessible to all this great city has to offer. If you're looking for a space to both adventure from and return to congregate with friends, look no further!

Family · Location · Nearby

Williams Avenue Hideaway

Welcome to our charming studio nestled in the heart of NE Portland! This cozy ground floor suite on the lower level of our home offers a perfect blend of comfort and convenience, making it an ideal home base for travelers seeking a local experience. Our space features a plush king bed, ensuring a restful night's sleep. Additional amenities include a thoughtfully designed kitchenette, full bathroom, smart TV, fast WIFI, washer/ dryer and a private patio all at your disposal during your stay.

Family · Value · Accuracy

Art Filled Historic Craftsman • Inner Eastside

An artist’s home filled with pieces I’ve created and collected, each chosen with intention. Two serene bedrooms with soft cotton bedding and 1.5 baths offer quiet comfort, while the house itself holds a calm, creative magic. In the heart of Portland yet peaceful and sheltering, it’s a short walk to the Convention Center, Lloyd Center, and the future Lloyd Center Music Venue. Come stay where beauty, artistry, and ease naturally meet. 420 OK in designated outdoor area — please be respectful

Family · Value · Checkout

Multnomah Village Hideout

Explore our new, artist-built bungalow in Multnomah Village, Portland. This cozy space sleeps four with a queen bed upstairs and a pullout couch downstairs. Steps away are charming cafes, shops, and a park with hiking trails and dog parks. Enjoy local activities like bingo and dining on pet-friendly patios. Complete with essentials including laundry and a breakfast nook, this bungalow is perfect for both short and extended stays, offering a unique Portland experience.

Family · Location · Hiking

Luxury Guesthouse | Spa Bath + Private Patio

A private design-forward luxury guesthouse in walkable Laurelhurst, just minutes from downtown Portland. ☀ 10 Mins to downtown + Airport ☀ Free private on-site parking ☀ Luxury queen bed • premium bedding ☀ Fully stocked chef's kitchen ☀ Private covered patio + fire pit | BBQ ☀ 65” 4K Smart TV + fast Wi-Fi ☀ Spa shower + heated bathroom floors ☀ Safe, walkable restaurants, coffee & transit ☀ Bikes to explore Portland ★ Your Luxury Oasis in the city awaits you!

Family · Value · Air conditioning

Vintage Portland Home ~ Steps from Mississippi Ave

Experience the perfect blend of vintage Portland charm and modern design in this beautifully updated home. Steps from the MAX line for easy access to the airport, Moda Center, Washington Park, and more, it's a hub for exploration. Walk to Mississippi Avenue's lively bars, restaurants, and boutique shops. Thoughtfully furnished and fully equipped, this cozy retreat has everything you need for a memorable stay. Relax, explore, and enjoy all that Portland has to offer!

Value · Family · Accuracy

Luxury Living on NW 23rd Ave, Walk Score 99

✨ Luxury 4BR Main Home on NW 23rd ✨ 🏠 Private 4BR main home above a separate garden-level suite 🛏️ 4 bedrooms, 5 beds — sleeps 12 🍳 Chef's kitchen with stainless steel appliances 🛋️ Spacious dining & living areas 💻 Fast WiFi & laptop-friendly workspaces 🌿 Private patio + top-floor balcony ❄️ AC & heating for year-round comfort 🚗 Driveway parking included; paid/metered street parking nearby 📍 Walk Score 99 — steps from Salt & Straw, shops & top restaurants.

Location · Family · Condition

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.

Value · Location · Barbecue

Holiday Home

Greetings Welcome to Portland! We hope that you will have a wonderful time in our beautiful city and that you will enjoy your stay here at Oasis in PDX We love entertaining and have put thought into creating different seat groupings, both inside and out, that invite people to relax both near to and apart from the main living areas, so that one-on-one conversations can take place without others in the group feeling excluded.

Family · Location · Quiet