House holiday rentals in Southeast Portland

Modern, Sleek & Stylish: 2 blocks from Hawthorne!

Designed to appeal to the most discriminating traveler, this large, family-friendly, original Portland Craftsman home has been lovingly designed to be a true home-away-from-home. With its Chef's kitchen, pillow-top beds, three private bathrooms, formal dining room, flat screen TVs and modern touches, this house is fully ready to be the highlight of your upcoming trip to the Pacific Northwest. This home is professionally managed by a local company; send us a message-we're ready to book your stay!

Location · Value · Biking

Hawthorne House - A+ Location! Pet Friendly!

Killer location!! An ez 2 min walk down the street from Hawthorne/Division in SE Portland! Enjoy the best restaurants, shops, bars PDX offers! Centrally located in great neighborhood! Main floor unit w/private access! Self check in! Bright and airy living spaces! Fully equipped kitchen for preparing delicious meals. Full sized wash/dryer. High speed Wi-Fi. Cozy bedroom w/plush queen-sized bed. Clean and modern bathroom stocked w/essentials. I'm excited to host you during your visit to PDX!!

Family · Value · Outdoor spaces

Live Like a Local in Artful Craftsman by Division

This spacious 1916 Portland bungalow offers a comfortable, inviting retreat packed with authentic character. Inside, the home features beautiful original woodwork, classic hardwood floors, and vibrant, curated artwork that gives the space a distinct creative energy. It is a wonderful place to unwind and recharge after a day of exploring. Enjoy your morning coffee out on the deep, covered front porch, or head out back to the private, leafy backyard garden to relax in a quiet, peaceful setting.

Location · Family · Biking

Mount Tabor Hideaway

Mt Tabor Hideaway is a fully stand-alone guesthouse at the back of our lot. Located at the foot of Mt Tabor, near SE Division & 60th. Enjoy privacy & comfort in its bright, modern & clean space. 2 BR with 3/4 Ba on each level, full kitchen, heat & A/C. French doors lead to your private outdoor patio. Reliable high speed internet, 600 mbps. Small smart TV. Enjoy a misty morning, drizzly afternoon or evening walk in Mt Tabor Park in a friendly neighborhood. City permit # 18–1 37613–0 00–00 – HO

Value · Family · View

Beautiful Portland Gem Minutes from Mt. Tabor

Welcome to Downstairs at 76th, a newly remodeled basement flat in a beautiful 1970s craftsman bungalow. Large windows usher an abundance of natural light into this unique, design-forward space. Step outside to explore Montavilla—an eclectic neighborhood with artisan cafes, a local theater, and a year-round farmers market—or immerse yourself in nature at nearby Mt. Tabor. A blend of charm and convenience, you're close to the best of PDX yet nestled in a cozy neighborhood. Welcome home!

Location · Value · Pets

The Plex PDX

Live Like a Local! The Plex will immerse you in mid century style and vintage charm with privacy and modern comforts-all in the heart of Portland. Sip coffee on the patio while you plan your adventures. Eat, drink, and play in this walkable central neighborhood. Just a few blocks from destination casual and upscale dining, coffee shops, boutiques, and historic Laurelhurst Park and Theater. Perfect for up to 4 people with driveway parking and a garage to store bikes and other gear.

Family · Location · Cleanliness

Heart of Hawthorne! Newly Remodeled, 99 Walk Score

✨ Charming 1907 Home Steps from Hawthorne Blvd ✨ 🌇 Walk score 99 — bars, restaurants & shops steps away 🛏️ 2 bedrooms, 3 beds, sleeps 6 comfortably 🍳 Full kitchen with dishwasher & stainless appliances 🛋️ Smart TV, fast WiFi & laptop workspace 👶 Pack ’n Play available by advance request (not stored onsite), kid-friendly & extended stays welcome ❄️ AC & heating for year-round comfort 🔒 Private entrance & driveway for 2 cars 🍽️ Less than 2 min walk to Hawthorne's best.

Family · Value · Walkability

Midcentury Modern - Backyard Oasis with Grill

Experience comfort and style in this 3-bedroom mid-century modern Airbnb in NE Portland, perfect for families, groups, or business travelers. Enjoy fast Wi-Fi, a dedicated workspace, and a fully equipped kitchen for easy home-cooked meals. Relax with backyard BBQs or explore Mount Tabor Park, local breweries. With top dining spots and attractions just minutes away, enjoy a relaxing and stylish Portland stay that feels just like home.

Family · Value · Nearby

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 · Hiking

3 BR 1 BA - Cozy Home - Walkscore 97 - Shopping

Stay at this top-rated Airbnb in Southeast Portland near the Hawthorne and Belmont districts. This stylish 3-bedroom, 1-bath pet-friendly vacation rental offers a full kitchen, cozy living space, and modern amenities. Walk to iconic cafes, bars, vintage shops, and parks. Ideal for families, couples, or friends looking to explore Portland’s top attractions while enjoying comfort and convenience in a prime walkable location.

Value · Location · Nearby

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.

Location · Value · Barbecue

Bright 3BR/2BA | Steps to Hawthorne | 5 Beds

Private 3BR/2BA Sunnyside apartment with five beds for up to nine guests. The main level has two bedrooms and one bath; the top floor has the primary suite and second bath. A living-room sofa bed completes the sleeping setup. Expect exterior and interior stairs, shared basement laundry, and the sounds of an active Belmont/Hawthorne dining district. Street parking only—read posted signs and do not block the driveway.

Value · Location · Hiking