Guesthouse holiday rentals in Southeast Portland

5 out of 5 average rating, 278 reviews

Clinton St Guesthouse • Walkable & Artistic

Stylish Clinton St guesthouse steps from cafés, bakeries, and transit. Features unique hand-painted floors, local Portland art (including child artists), and a small library of Portland authors. Queen bed, blackout shades, AC, desk, fast Wi-Fi, washer/dryer, and a coffee station with Moccamaster, grinder, AeroPress, French press, pour-over, and local beans. Walk to OK Chicken, Salt & Straw, Loretta Jean’s, Cookies, New Cascadia (gf bakery) Oma’s Hideaway, Cibo, Someday, The End, and food carts.

A welcoming exterior view of the cottage is shown, featuring a manicured front garden filled with various shrubs and seasonal flowers. The white brick façade of the home contrasts with the lush greenery, while large windows allow for ample natural light to enter the space.

4.98 out of 5 average rating, 617 reviews

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.

A modern kitchen area is showcased with gray cabinetry and a white tile backsplash. A double sink is positioned in front, complemented by a stove and microwave. A dining area is visible across from the kitchen, featuring a seating arrangement and a sofa.

4.99 out of 5 average rating, 246 reviews

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!

An open floor plan features a kitchenette with white cabinetry and a countertop. A wooden dining table with four chairs stands beside a cozy seating area, where a folded sofa and armchair are visible. Bright overhead lights illuminate the space, showcasing exposed beams and warm wood flooring.

4.98 out of 5 average rating, 244 reviews

Open garden studio in the heart of the SE Portland

This spacious and open floor plan garden studio is in the heart of SE Portland. Within steps of the Belmont District, a few blocks from Hawthorne Blvd, Division St, Stark St, 28th & Burnside, and so much more. You can easily walk, bike, or bus to awesome places to see, drink, eat, visit, etc. An excellent launching point for all of the Rose City, we are a short bike ride or bus to Downtown, museums, and concert venues. Enjoy all that Portland has to offer at this centrally-located neighborhood.

The open kitchen and living area feature vaulted ceilings and natural light. A fully equipped kitchen is highlighted by wood cabinetry, a gas stove, and a breakfast counter with three bar stools. Subtle green accents decorate the walls, complemented by modern furnishings.

4.82 out of 5 average rating, 198 reviews

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!

A light-filled living area features two armchairs positioned beside large windows, showcasing views of surrounding greenery. A plush sofa offers a comfortable seating option, while a small, decorative table holds a plant. A television is mounted on the wall, enhancing the modern design.

5 out of 5 average rating, 115 reviews

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!

An open-space studio features high ceilings with wooden beams, enhancing the airy feel. A queen-sized bed is set against the wall with soft linens. A small kitchenette and dining area are visible, with a full bathroom enclosed in glass. Natural light brightens the interior.

4.96 out of 5 average rating, 514 reviews

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

4.98 out of 5 average rating, 130 reviews

Coda | Walkable Woodstock Guesthouse | Portland

Unwind in this elegant, light-filled guest house featuring tall ceilings and abundant natural light. Located in Portland’s desirable Woodstock neighborhood, it’s a short walk to acclaimed restaurants, a vibrant food cart pod, grocery stores, and a local brew pub. Coda offers a peaceful retreat with curated musical instruments, a premium Sonos sound system, and a fully equipped kitchen and baths—an inviting space to relax and recharge after a day in the city.

A modern garden retreat with sleek black exterior features a welcoming entrance framed by natural greenery. Concrete pathways lead to a patio area with seating, and large windows invite light into the space. The surrounding wooden fence provides privacy in a serene outdoor setting.

4.99 out of 5 average rating, 412 reviews

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.

4.86 out of 5 average rating, 889 reviews

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.

An open living space features a comfortable sitting area with a sofa and stylish chairs. A dining table accommodates four, while the kitchen area showcases modern appliances. Natural light filters through multiple windows, illuminating the spacious sleeping area with a large bed in the background.

4.99 out of 5 average rating, 401 reviews

The Loft: Modern Open space in Southeast Portland

A private, open, airy, and stylish space located over a detached garage behind the main house. This is a great neighborhood that is close to public transportation and major roads. Easily walk to bike rentals, food carts, restaurants, local bars, and main shopping areas. We are looking to provide a safe and comfortable space. We love to give suggestions and recommendations on places and things to do while in Portland and Oregon.

Guesthouse in Ladd's Addition

An open living space features modern kitchen cabinetry with an island, complemented by pendant lighting. A cozy sofa adorned with decorative cushions faces a coffee table, with a staircase leading to the upper floor. Natural light streams through the windows, enhancing the bright atmosphere.

5 out of 5 average rating, 150 reviews

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.

Popular amenities for Southeast Portland guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

A modern studio space showcases a spacious bed with soft bedding, flanked by a decorative wall featuring floral designs. A cozy seating area is present alongside a dining nook, creating a functional layout. Natural light filters through the nearby window, enhancing the inviting atmosphere.

4.88 out of 5 average rating, 192 reviews

Three Wishes Studio

An open living space is equipped with a modern kitchen featuring white cabinetry and stainless-steel appliances. A spacious bed is positioned nearby, with natural light illuminating the area. A small dining bar with stools creates a welcoming space for meals or casual gatherings.

4.99 out of 5 average rating, 153 reviews

Luxury Loft ~ Bidet, Skylight & Bed for Royalty

A bright studio space features a minimalist design with a dividing bookshelf showcasing books and decorative items. A comfortable gray sofa is positioned in front of a small dining area with bar stools. The queen-sized bed is visible through a separation, with light filtering through the window.

4.98 out of 5 average rating, 741 reviews

Tiny House, Big Charm

A welcoming entrance is framed by wooden siding and a covered porch. Potted plants are positioned on either side of the dark grey door, which features a modern handle. The pathway leading away from the door is visible, bordered by greenery.

4.95 out of 5 average rating, 520 reviews

The Tiny Big Guest House

An open layout features a kitchen with a central island and two chairs, complemented by stainless steel appliances. Natural light streams through a window overlooking greenery. A spiral staircase leads to the loft bedroom, while polished wooden flooring enhances the inviting ambiance.

4.96 out of 5 average rating, 170 reviews

The Loft in Hawthorne Tabor

An inviting outdoor area features a wooden bench in a small courtyard, framed by a natural wood fence. The entrance to the studio is highlighted by large glass doors, allowing a view of warm interior lighting. Lush greenery adds a peaceful ambiance to the space.

4.94 out of 5 average rating, 793 reviews

Hawthorne Wisteria Retreat

A cozy sitting area is featured, with a light-colored sofa adorned with patterned cushions. A wooden coffee table sits in front of the sofa, and natural light fills the space through a window flanked by sheer curtains. A floor lamp stands beside the sofa.

4.91 out of 5 average rating, 875 reviews

Modern Garden Studio Self Check & Private Entrance

A detached studio features a charming A-frame design, surrounded by lush greenery. A stone patio with outdoor seating complements the inviting entrance, where large windows allow natural light to fill the space. The setting provides a serene atmosphere, ideal for relaxation.

4.98 out of 5 average rating, 688 reviews

The Westmoreland Lighthouse - Private studio in SE

Guesthouses with a patio

A spacious living area features a large gas fireplace and a mounted television. Comfortable seating includes a plush couch and two accent chairs. Natural light enters through nearby windows, illuminating a casual dining table. Decorative elements provide a cozy yet modern ambiance.

4.96 out of 5 average rating, 120 reviews

Family Friendly SE Portland Getaway w/2 Bedrooms

Guesthouse in Southwest Portland

A serene backyard oasis features a cascading water feature flowing over wooden planks and rocks. The modern tiny home with a dark exterior stands behind an elevated wooden deck, surrounded by lush greenery. Outdoor seating is visible, offering a calm retreat.

4.93 out of 5 average rating, 160 reviews

Brand New Tiny Home/Pottery Studio in Cute Village

Guesthouse in Laurelhurst

A well-lit guest space includes a spacious bed, modern television, and a chic coffee table. Two large windows offer ample natural light, accompanied by a small dining set and a comfortable chair. The hardwood floor adds warmth to the inviting atmosphere.

4.93 out of 5 average rating, 106 reviews

Stylish Laurelhurst Guesthouse

A cozy studio space is depicted, showcasing a comfortable seating area with a neutral-toned sofa. An open kitchen with bar seating is visible in the background, alongside large glass doors leading to a fenced backyard. A television stands against the wall, ready for entertainment.

4.96 out of 5 average rating, 269 reviews

Bright, Private & Cozy with Yard

Guesthouse in Northeast Portland

A detached entrance is seen with a wooden door and large windows, framed by a clean gray exterior. A small patio area features a table and two chairs, inviting relaxation. The surrounding landscape includes gravel and low-maintenance plants, enhancing a sense of privacy.

5 out of 5 average rating, 118 reviews

Private urban retreat, new build, 1bedroom, sleep4

4.88 out of 5 average rating, 177 reviews

SE City Spa Retreat

4.94 out of 5 average rating, 185 reviews

The Yellow Cottage - Private, Peaceful, & Near PDX

Guesthouse in North Portland

The exterior of a two-story studio is framed by lush greenery and trees. The building features a spiral staircase leading to a private balcony with black railings. A shared garden area is visible below, with a hammock and various plants around the space.

4.98 out of 5 average rating, 269 reviews

Spacious, bright garden studio on Peninsula Park

Guest house rentals with a washing machine and dryer

Guesthouse in Laurelhurst

The living area features large windows allowing natural light to fill the space. A comfortable sofa is complemented by a round coffee table and a stylish accent chair. A colorful area rug adds warmth, while modern artwork enhances the contemporary decor.

4.94 out of 5 average rating, 435 reviews

Chic Guest House in the Heart of the City

A detached guest house is viewed from the front, showcasing a spacious lawn with a private putting green in the foreground. The covered porch features comfortable seating, and lush greenery surrounds the home, enhancing its inviting outdoor space.

5 out of 5 average rating, 239 reviews

Separate spacious guest house over garage.

A modern yellow carriage house is set in a park-like backyard, surrounded by greenery. The structure features a second floor balcony with outdoor seating, and stairs leading down to a landscaped yard. Mature Douglas Fir trees provide shade, while a garage is located below.

5 out of 5 average rating, 119 reviews

Stellar Sellwood Carriage House

Guesthouse in Laurelhurst

A modern kitchen is showcased with sleek cabinetry and stainless steel appliances, including a refrigerator and an oven. A small dining table sits beside a cozy seating area, while a washer and dryer are positioned near the back. Natural wood ceilings add warmth to the space.

4.99 out of 5 average rating, 628 reviews

Little Cedar House Cottage near coffee and shops

A pathway leads to the entrance of a two-level guest house, framed by lush greenery and a wooden fence. The entrance features a bold red door that contrasts with the blue exterior of the house, creating an inviting approach.

4.94 out of 5 average rating, 257 reviews

Charming, private 2-level guesthouse-Woodstock

Guesthouse in Northeast Portland

A bright, open studio space features large windows that allow natural light to fill the room. A cozy seating area with a gray sofa and glass table complements a spacious bed, while a small dining table with two chairs is placed nearby.

4.99 out of 5 average rating, 675 reviews

Contactless Clean Private Treetop Studio

A modern living area features a gray sofa adorned with an orange pillow, complemented by a rug in rich red tones. The space includes a well-equipped kitchen island with green cabinetry and stainless steel countertops, alongside a map on the wall that adds a touch of local interest.

4.96 out of 5 average rating, 359 reviews

Woodstock modern apartment

An open living area is showcased, featuring a light gray sofa and a wooden coffee table. Natural light floods through double French doors, which lead to a private patio. Artwork adorns the walls, while a small desk stands next to the entrance.