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!

Value · Family · Parking

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 · Location · Wi-Fi

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

Location · Value · Heating

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.

Family · Value · TV

Market Street Guesthouse PDX

This is THE ONE! A perfect blend of upscale finishes, fixtures, and appliances in a beautiful and welcoming cottage. Soaring ceilings welcome the weary traveler into a space that offers fine linens, a fully stocked kitchen, two full baths with heated tile floors and a custom, versatile layout. No expense was spared building the space: the vibe is true Pacific NW, with wood trim, warmth and beauty all around. IDEAL walkable location smack dab amongst Portland's coolest neighborhood amenities!

Family · Location · Biking

Luxury Craftsman | AC | King Beds | Portland Theme

The "Clover Craftsman" is your perfect base to explore Portland, the mountains, the coast, or wine country. Each of our 5 uniquely themed rooms celebrates what makes Portland unique: stunning roses, 12 iconic bridges, nearby forests, beloved bike scene, and TV show Portlandia. 10 min to Division/Hawthorne, 15 min to downtown or PDX Airport. Gather around the dining table for 10, unwind in multiple living spaces, and sleep soundly — 4 kings plus 2 twin XLs ensure everyone sleeps comfortably.

Family · Value · Comfort

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!

Family · Location · Layout

Mid-Century Dream | 3BR/2BA | Heart of Hawthorne

✨ Mid-Century Dream Home in the Heart of Hawthorne ✨ Your stylish Portland escape, fully renovated with custom details: 🏡 3 queen bedrooms · sleeps 6 🛁 2 full baths 🪵 Custom walnut cabinets & sustainable NW finishes 📶 Gigabit fiber WiFi + YouTube TV & Netflix 🍳 Modern kitchen with new appliances ❄️ Central AC & heat 🅿️ Free off-street parking 🚶 Walk to Hawthorne's best restaurants, thrift shops, live music & cafes in seconds. Your mid-century modern Portland home base! 🌲

Value · Location · Bathroom

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 · Kitchen

Heart of Hawthorne Craftsman | Walk Score 92 | Mod

Centrally located in the Heart of Hawthorne, this gorgeous, newly renovated and spacious 1925 Craftsman home (with numerous upgrades and finishes) is within walking distance to some of the best eateries and coffee shops in Southeast PDX, including ¿Por Qué No?, Apizza Scholls, Fried egg, Ruby Jewel, Common Grounds, I'm in love and Black Ink cafe. This incredible home is great for couples, business travelers, families (with kids) and big groups!

Family · Value · Kitchen

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 · Location · Hospitality

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 · Family · Walkability