House holiday rentals in Southeast Portland

The Nest/Portland.Peaceful.Fun

The Nest is situated on the second and third floors of this charming Old Portland home. The house is central to everything Eastside, boasting a walk score of 94! Belmont & Hawthorne have incredible eateries, bars and shopping only a few steps away. It is also very close to the heart of the Division, Stark, SE 28th & Burnside commercial districts. It's a 5 minute walk to Laurelhurst Park, voted the most beautiful park on the west coast, & only 2 miles from downtown, The Pearl and Mt. Tabor Park.

Cozy Bungalow in Ladd’s Addition • Walk/Dine/Shop

Welcome to “Happy Place”, your cozy retreat that feels like a home-away-from-home in the vibrant heart of Portland! Our sanctuary in the bustling SE Clinton/Division area offers fast internet, perfect for work-from-home needs, and is a short stroll from top restaurants, bars, and boutiques. Boasting a walkability score of 92, city exploration is a breeze. Ideal for foodies, culture lovers, and outdoor adventurers, we provide FREE on-site parking and embrace the spirit of Portland living.

The Flying Whale-MountTabor.

You will have full reign of the top (street)level of the home. Host lives downstairs in the sun basement. You are the only ones who will enter through the front door, and you’ll have a reserved parking space in the double driveway. Your space includes a double queen bedroom, an office with an extra king bed, full bathroom, a fully equipped kitchen, dining/living room with wood burning fireplace and stunning views, a full laundry room, a wrap around deck with outdoor table and chairs.

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.

Live Like a Local in Artful Craftsman by Division

Beautiful 1916 Portland bungalow - bursting with character, original woodwork & striking local artwork. Located on a quiet residential street, it is steps away from the bustling Division/Clinton corridor filled with restaurants, shops, and bars!. Easy street parking surrounds the whole house in this charming, tree-lined neighborhood. From the covered front porch to the charming backyard, and everything in between- spread out and enjoy all Portland has to offer!

Casa Dolce Casa / Home Sweet Home in Alberta Arts

Welcome to my charming detached guest house, filled with touches inspired by my home country, Italy. Experience the quaint charm of a tiny house with the comfort and openness of a traditional home. Stroll to Alberta Arts District's restaurants, bars, breweries, food cart pods, and unique local shops. Explore the Oregon Coast, local hikes, and wineries. Public transport is nearby for city exploration, and the airport is just a 12-minute drive away.

Cozy and Walkable 1 bedroom daylight basement

Our basement has been newly renovated. Brand new bedroom, beautiful bathroom and living space. The living space includes a 57” Smart TV and couch. The wet bar features a mini fridge, sink and Keurig Coffee maker. The bedroom has 1 queen sized bed with hotel luxury 1800 bedding sheets, a dresser, full length mirror and natural light window. Our house is centrally located with dozens of restaurants, bars and coffee shops just a short walk away!

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.

Tiny Farmhouse - Walk to Local Shops & Restaurants

✨ Charming Tiny House in SE Portland ✨ 🏡 Cozy private retreat with garden & backyard 🛏️ 1 bedroom with queen bed for 2 🍳 Full kitchen with stove, fridge & coffee maker 🌿 Private entrance & outdoor space 💻 Laptop-friendly workspace with fast WiFi 🐾 Pet-friendly — bring your furry friend ❄️ AC & heating for year-round comfort 🧺 Washer & dryer in unit 🍽️ Heart of SE Portland, walk to shops & cafés. Free street parking.

Portland Regency Moderne - an Artist’s Home

Maximalism meets jungalow glam in our best expression of modern Hollywood Regency for the Rose City. Hand-painted cranes and geometric tropical boho murals, alongside gilded and colorful decor, adorn this centrally-located, mid-century-ranch artist’s home. Private access to 2BR/1BA home, includes a full kitchen, dining area, and sunset views of the West Hills from the front deck.

Tabor Retreat

Charming, woodsy, spacious one bedroom basement apartment. Large full kitchen, bathroom, washer and dryer, living room with gas fireplace insert. Private, easy access, lighted entrance. Convenient access by bus to downtown Portland and Airport. Includes beautifully landscaped grounds, patio, and access to Mt. Tabor park with running, biking, hiking trails and tennis courts.

Color Splash - Fast WiFi - Heart of Hawthorne

✨ Stylish SE Portland Studio in Hawthorne District ✨ 🏡 Private entrance — entire place to yourself 🛏️ Cozy 1BR with queen bed & AC 🍳 Full kitchen with dishwasher & cookware 💻 Dedicated workspace with fast WiFi 🐾 Pet-friendly — bring your furry friend 🧺 Coin-operated laundry on-site (basement) 🍽️ Walk to Hawthorne's best cafes, breweries & shops. Free street parking.