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.

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.

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.

Tabor Cottage: Detached Guest House SE Portland

Mt. Tabor Cottage is a quiet, cozy, detached one bedroom house.with a private, fenced patio. In the South Tabor neighborhood, we are close to Mt. Tabor park and walking distance to several restaurants. It's a 15 minute car ride to the airport or about 17-20 minutes to downtown Portland and only a 5 -7 minute drive to Montavilla, Division St and Hawthorne Blvd restaurants, bars and shopping. Street parking is always available on the block, often next to property or within 150ft, 30 second walk!

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!

Modern Luxe Loft on the Hawthorne Strip

Welcome to your perfect Portland stay! This cozy and modern Loft is located steps from famous food carts and the Hawthorne strip, which is the best place to walk and shop in all of PDX. It is a brand new build with sleek, minimal fixtures, mixed with vintage-inspired textiles and bold color pops- eclectic, just like our city! The space is perfect for stylish travelers or for the professional that wants a quiet yet luxurious place to work-comfort, style, and convenience! A perfect stay!

Dwell | Upscale Woodstock Retreat | Walk to Dining

Now Net Zero Energy! Dwell has 18 solar panels that cover more electricity that the building uses! New modern House with gourmet kitchen. Enjoy the tile shower with endless hot water, smart tv, and cozy furniture. Short walk to Woodstock village with Double Mountain Brewing, New Seasons. Easy access to public transportation, or sit back and relax on the patio with firepit. Light and bright guest house and you have the place to yourself. There is a fenced yard that is pretty private.

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.

Urban Oasis Retreat + sauna

Our guest house is a completely private space, accessible by an outdoor walkway, and has an outdoor patio. We designed the space to be light-filled, feel cozy yet roomy, fitting a lot into a small space. Vaulted ceilings, a ceiling fan, full kitchen, bathroom, a bed alcove with a comfy queen mattress and soft bedding and lots of extra touches. Our 335 sq ft guest house is fitted with all you'll need for your time in Portland.

Exceptional East Moreland Guesthouse/ Reed College

We take Covid 19 safety standards seriously! Artfully decorated street-level garden apartment in a quiet, residential neighborhood lined with 100 year old trees. 15 minute walk to Reed College and nearby hiking/cycling trails. Private garden patio, gas 'woodstove' in the living room- lots of ambiance and comfort. Fully equipped kitchen. Enjoy the complimentary HBO/ Netflix. We use nontoxic cleaning materials. #superhost

Family Friendly SE Portland Getaway w/2 Bedrooms

Located in one of Portland’s most desirable areas bordering Woodstock & Eastmoreland this Guesthouse offers a quiet, spacious space while you explore the city. Just blocks away from Reed College and a 5 min drive to Sellwood/Woodstock restaurants. Highlights: 1,200 sq. ft King bed - 2x Gas fireplace & Range Self check in Washer dryer Fully equipped kitchen 20ft lofted ceiling 75' TV Off street parking

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.