Guest house holiday rentals in Southeast Portland

Luxury Loft ~ Bidet, Skylight & Bed for Royalty

*We offer a 15% weekly stay discount and 20% monthly stay discount. *Photos of all businesses in this listing are < 1.0 mile away. *All Races, Gender Identities, Sexual Orientations, Religions Welcome. Our family welcomes you to a slice of our Portland life. We live in a quiet residential neighborhood where the sounds you are most likely to encounter are the distant squawks of our backyard chickens, the pitter-patter of raindrops on the skylight, or the occasional children's squeal or dog bark.

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.

Eastmoreland Private Guest Suite by Reed College

Private Guest House Studio Apartment in one of SE Portland's historic neighborhoods - Eastmoreland. With quick access to all the best things Portland has to offer. Situated two blocks from Reed College entrance and a short walk to golfing, Sellwood, Westmoreland, and Woodstock restaurants as well as bus lines and the Trimet MAX Orange Line. If you are looking to explore the wonderful city of Portland, or if you are looking for a quiet comfortable tiny home retreat you have found your getaway!

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!

Willow Tree Guesthouse

Pet friendly guest house in SE Portland 1 block from the heart of SE Division street. Located on a quiet dead-end street, with a full kitchen, ground floor bedroom/bathroom, spacious walk-in shower, and super cozy upstairs loft makes for the perfect work remote office. Grocery stores in every direction, neighborhood wine shop, and weed shop, restaurants and bars right around the corner. Location and walk score - 100! Gigabit fiber internet - good bandwidth for the digital nomads!

The Westmoreland Lighthouse - Private studio in SE

We've dubbed this stunning, fully detached studio the "Lighthouse" because of the way natural light pours through the 550-square-foot studio's many windows and dances off its walls and vaulted ceilings. An open loft offers soothing views. We are tucked into the Westmoreland neighborhood's quiet residential area, but are only a five minute walk from more than 20 restaurants and entertainment features. Westmoreland Park, Reed College and downtown Portland are just minutes away by car.

Bright, Private & Cozy with Yard

Relax in this private, bright and cozy studio space with fully fenced back yard. Nestle up by the outdoor fire, or enjoy a sunset under the covered patio. Equipped with TV, WiFi, and FireStick so you can connect to your favorite shows easily. Kitchen has microwave, mini-refrigerator, induction stove, dishwasher, and all of the supplies you would expect! Enjoy cozy Brooklinen bedding (it's the best!). Full bathroom with washer/dryer, walk-in shower, and ultra soft bath towels!

Woodstock•Net Zero•Chef Kitchen•Firepit•Pet-OK

Private, net-zero 1-bedroom guest house in Woodstock—no shared walls or space. Walk to Double Mountain Brewing, New Seasons, restaurants, and transit, then relax in a fenced yard with a firepit patio. Enjoy a custom kitchen with Sub-Zero fridge and Miele range, endless-hot-water tile shower, and bright modern furnishings. Dogs welcome; self check-in. Sleeps up to 4 with a queen bed, queen sofa bed. Dwell has 18 solar panels that cover more electricity than the building uses!

SE Portland Guest Cottage

The guest cottage offers self check-in. It is located in a quiet neighborhood in SE Portland. High ceilings make this studio airy and bright. We think of it as a perfect hotel room without the hotel. The small galley kitchen has everything you need to cook a gourmet meal including filtered water. There is a full bathroom with tub and shower. The cottage stands on its own making it perfect for coming and going as you please. City of Portland Permit #24 013532

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.

Romantic Casita. HotTub and Firepit. Pets Welcome!

Come and stay in our romantic, Mediterranean Casita. This private cabin is built for singles and couples. Featuring a hot tub, fenced courtyard, fire pit, covered patio, white Linens, handmade ceramics, rustic furniture, peaceful art and off street parking. Though secluded, you're just a short walk from the vibrant Woodstock BLVD. Enjoy a unique, tranquil retreat designed for relaxation and intimacy, comfortably fitting two guests. Pet's are welcome.