Holiday houses in Southeast Portland

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.

Private Oasis! Cozy & Close to Everything!

Beautiful, one of a kind guest house nestled in one of Portland's most desirable locations! This chic and cozy space features vaulted ceilings, all new appliances, comfortable furniture, and tons of natural light! A quiet street, peaceful atmosphere (and awesome soaking tub) make this the perfect spot for relaxation. Enjoy exploring the surrounding neighborhood and easily walk to shops, restaurants, bars and Laurelhurst Park! Central location allows quick travel to other areas of the city!

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!

IndigoBirch: Luxurious Zen Garden Retreat: Hot Tub

Look no further- as a member of The IndigoBirch Collection™️, our guest home stands as a top-tier experience on Airbnb. Located two blocks away from Reed College, IndigoBirch is nestled on a quiet tree-lined street in the highly desired & historic neighborhood of Eastmoreland. Our location is perfect for the adventurer looking to explore Portland. The guesthouse is two blocks away from public transportation, 12 minute drive to downtown Portland, and 20 minutes to PDX Airport.

Château Woodstock – Cozy Stay Near Cafés & Parks

This detached studio home is located in the Woodstock neighborhood, which is one of the few remaining ungentrified areas in Portland. Located a short drive from highway 205 you can get to any part of the city quickly or explore the local bars, restaurants, and parks of SE Portland. There is a private entrance where you can come and go as you please. We're happy to interact with you as little or as much as you prefer, so don't be a stranger or be as private as you like.

Newly built studio in perfect SE location

A cozy newly renovated space with a modern motif. Plenty of natural light, high ceilings. Large walk in shower,walk in closet, washer +dryer and kitchenette with microwave. Queen size bed with European style bedding:fitted sheet, pillows and king size duvet with duvet cover, NO FLAT SHEET or TOP SHEET. The apartment is located in one of the best neighborhoods on the east side.Close to downtown, bus lines, bikes and scooters rental,shopping,casual and fine dining.

The Loft in Hawthorne Tabor

Loft style guest house with private entrance & private porch in a quiet and convenient Hawthorne Tabor neighborhood. Location: Explore the many restaurants, bars, boutiques, etc in less than 10 min walk along SE Hawthorne Blvd including: Por Que No?, Tabor Bread, New Seasons, Farmhouse Kitchen Escape to the tranquility of Mt Tabor park & trails after an enjoyable 20 min walk through West Tabor neighborhood 15 min drive to PDX Airport 15 min drive to Downtown

Mt Tabor Tree House, Hidden Urban Retreat

Our Mt Tabor Treehouse is an incredible and unique escape that invites you to relax and connect with nature without sacrificing any modern amenities, all in the heart of the City of Roses. Nestled underneath towering Douglas Fir trees, this fully equipped tiny house in a tree is surrounded with nature, along with immediate access to miles of mixed use trails and walking distance to one of Portland’s best restaurant, coffee shop and local market “Coquine”

Award-Winning Guest House with Private Entrance

Featured in Dwell Magazine; Winner of “Best Whole House Design” by Oregon Home Magazine, this spacious urban garden retreat has one-bedroom with a luxurious king bed, full bathroom, and fully equipped kitchen. Tucked away in a tranquil urban oasis, the space is filled with natural light and boasts a private garden entrance. Wake up refreshed in the crisp, white bedroom and slide open the rustic barn door for a coffee on the patio of this zen retreat.

Deluxe 5★ Guest House ❤️ Close-in Convenience

Enjoy modern amenities and close-in convenience at our Craftsman home in historic Laurelhurst. This spacious retreat is private, easy living for business visitors, pleasure seekers, and family fun. It’s a pleasant stroll to the best restaurants and shops, plus instant access to public transport. Read our stellar reviews and book with confidence. 10 minutes to Downtown; 15 to airport

Portland's Best 1BD in Hawthorne | Newer Building

Step outside and explore the charm of Portland's Hawthorne neighborhood, filled with vintage shops, local bookstores, and cozy coffee spots full of character. Stroll past colorful murals, browse unique boutiques, and take in the laid-back, creative vibe. Whether you're here to relax, explore, or a little of both, this welcoming space is a great place to call home through your stay.

Stylish Hawthorne 1BR w 90 WalkScore

✨ Walkable Hawthorne 1BR with Fast WiFi ✨ 🛏️ Cozy 1-bedroom with queen bed 🍳 Full kitchen with dishwasher & coffee maker 🛋️ Cable TV & fast WiFi 💻 Laptop-friendly workspace for remote work 🐾 Pet-friendly - bring your furry friend ❄️ Living-room mini-split A/C + heat 🔒 Private entrance - entirely yours 🍽️ Steps from Hawthorne cafes, brewpubs & shops. Free street parking.