Holiday rentals in Southeast Portland

Woodstock Farmhouse

Modern farmhouse in the heart of Woodstock featuring 1 bedroom, 1 bathroom, living room, a fully stocked kitchen, AC, and a private deck. This space is a new construction farmhouse with lots of privacy. Enjoy off street parking with a private garden path leading to your front door. Just a short walk to some of SE Portland's hottest spots including Double Mountain Brewing, New Seasons Market, Otto's Sausages, Cloud City Ice Cream, Grand Central Bakery, The Woodstock Farmer's Market, and more.

Woodstock Tiny House

Detached, very small (300 sq ft) guest house in the Southeast Portland neighborhood of Woodstock. Lots of walkable eateries as well as New Seasons and Safeway within a 5 minute walk. Close to Reed College, Woodstock Village, Springwater Trail, Southeast Portland Neighborhoods, Public Transportation. You’ll love the location, the outdoors space, and the ambiance. Good for couples, solo adventurers, and business travelers. TV (Netflix enabled!), A/C (summer months), heat, coffee, fridge/freezer.

Cozy Guest Cottage in Woodstock Neighborhood

A bright and cozy cottage located near Reed College, Woodstock's restaurants/coffeehouses, Trader Joe's and public transit. This residential neighborhood is ideal for a quiet retreat for all visitors. The private guesthouse is outfitted to make your stay comfortable including a spacious bathroom with a walk in shower and a heated floor. Plus, you may want to enjoy a cup of coffee on your own patio located behind the Airbnb. As an added bonus, breakfast items and home baked treats are provided.

Walk to Se Division from a Sleek, Architect Designed Space

My wife, Raechel, and I originally designed and built this ADU ( accessory dwelling unit ) with the intention of living there full time, but due to a change of plans, it's available to you. The space was designed by Buckenmeyer Architecture, and was constructed by me. Our space features many unique elements such as: burnt cedar siding, 16' multi-slide window wall (please open and close slowly), and moveable cedar slat screens/ We hope you enjoy the space and neighborhood as much as we do!

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!

Elegant SE Portland/Reed College BLUE MOON SUITE

The Blue Moon Suite is a cool, comfortable and convenient apartment within a home to stay if you're visiting Reed College, are in Portland for business (downtown is only 15 mins away) or if you are just touring the city. We look forward to welcoming you into our home and aim to make your stay as comfortable as possible while taking your privacy seriously & offering private access to an elegantly decorated yet comfortable one bedroom lower level apartment with everything that you might need.

Architect-designed house in SE Portland’s MtTabor

Our modern guesthouse is a clean, private space filled with natural light. The front gate opens into a private, landscaped courtyard landscaped with jasmine, a Japanese maple tree, rhododendrons, and ferns. We are conveniently located near Mt Tabor Park that has walking trails and a spectacular view of the city. We are also close to several popular neighborhoods with shops, cafés, and restaurants. We welcome people of all backgrounds to stay here and enjoy beautiful Portland.

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.

Modern and Bright Laurelhurst Abode

Our one bedroom cottage is completely private, accessible by a separate walkway, and has an outdoor patio. Extra time was spent choosing finishes and creating a modern, comfortable, and light-filled space. You’ll find everything you need for a weekend in Portland, or a long-term stay. We’ve outfitted a full kitchen, full bathroom with luxurious tub and plush towels, a bedroom with a queen mattress and soft bedding, washer and dryer, and lots of extra touches.

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.

★ Modern Division Street Hideout ★

✅ 5 ⭐️ location! ✅ Sauna 🧖‍♀️ ✅ King Size Bed ✅ Modern finishes ✅ Washer + Dryer ✅ Roku Smart TV ✅ ecobee smart thermostat Bright one-bedroom flat with private access and patio located in the mix of all the restaurants, shops, galleries, and nightlife Division Street has to offer. Aside from the incredible location, you’ll have a kitchen, Roku TV, washer + dryer, and a king size bed. Oh, and a sauna!! 😎

Sage Guest House

Enjoy free parking adjacent to the Guest House! Located steps from the Hawthorne District and nestled in the historic Ladd's Addition neighborhood, this guest house is near fine restaurants, coffee shops, entertainment venues, and food carts . Stroll in the shade of century old Elm trees, and discover four public rose gardens located at the compass points within this 1890 neighborhood.