Guesthouse holiday rentals in Southeast Portland

A modern farmhouse exterior is presented with striking red siding and white trim, complemented by a manicured lawn. Two garage doors and a side entrance door are visible, framed by potted plants. Large windows allow natural light, enhancing the exterior's welcoming appearance.

4.95 out of 5 average rating, 346 reviews

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.

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, 204 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.

5.0 out of 5 average rating, 122 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!

4.98 out of 5 average rating, 624 reviews

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.

Guesthouse in Woodstock

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 patio located behind the Airbnb. As an added bonus, breakfast items and home baked treats are provided.

The exterior of a charming blue guest house is framed by greenery and decorative stones. A welcoming entryway is highlighted with two white chairs, while a wooden awning provides shade over the entrance. The path to the door is lined with pavers and gravel.

4.99 out of 5 average rating, 223 reviews

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!

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, 690 reviews

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.

A bright sleeping area features a spacious yellow bedspread and decorative stained glass window above a small nightstand. Soft lighting is provided by wall sconces, and the smooth wooden floor enhances the studio's contemporary design.

4.94 out of 5 average rating, 141 reviews

Garden studio in Laurelhurst

Cozy, sunlit studio apartment with great morning light from two skylights overhead. Our studio is the perfect place to explore Portland from. We're a short walk to the best of historic Southeast Portland--Belmont, Stark, Burnside, Hawthorne, and Division streets. Many of Portland’s beloved restaurants, bars, and coffee shops, along with towering pines and spring-fed pond of Laurelhurst Park, are just around the corner. Enjoy the garden patio for morning coffee or drinks at night.

A cozy bedroom features a spacious bed adorned with a patterned duvet and decorative pillows. A flat-screen TV is mounted on the wall, while a small dining table with two chairs is positioned nearby. Natural light filters in through the windows, highlighting the wooden floors.

4.96 out of 5 average rating, 567 reviews

Newly built studio in perfect SE location

A cozy newly renovated space with a modern motif. Plenty of natural light, high ceilings. Large walk in shower,walk in closet, washer +dryer and kitchenette with microwave. Queen size bed with European style bedding:fitted sheet, pillows and king size duvet with duvet cover, NO FLAT SHEET or TOP SHEET. The apartment is located in one of the best neighborhoods on the east side.Close to downtown, bus lines, bikes and scooters rental,shopping,casual and fine dining.

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.

4.97 out of 5 average rating, 175 reviews

The Loft in Hawthorne Tabor

Loft style guest house with private entrance & private porch in a quiet and convenient Hawthorne Tabor neighborhood. Location: Explore the many restaurants, bars, boutiques, etc in less than 10 min walk along SE Hawthorne Blvd including: Por Que No?, Tabor Bread, New Seasons, Farmhouse Kitchen Escape to the tranquility of Mt Tabor park & trails after an enjoyable 20 min walk through West Tabor neighborhood 15 min drive to PDX Airport 15 min drive to Downtown

4.98 out of 5 average rating, 134 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, 418 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, 900 reviews

Guesthouse in Woodstock

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.

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, 196 reviews

Three Wishes Studio

4.94 out of 5 average rating, 949 reviews

A spacious studio cottage is bathed in natural light. Wooden beams adorn the vaulted ceiling, while a queen size bed with a floral green coverlet occupies one side. A kitchen area, a small table, and two chairs are visible, with warm yellow curtains framing the windows.

Guesthouse in Mt. Tabor

The Cedar Cottage

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, 248 reviews

Eastmoreland Private Guest Suite by Reed College

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, 753 reviews

Tiny House, Big Charm

5.0 out of 5 average rating, 285 reviews

Clinton St Guesthouse • Walkable & Artistic

The charming exterior of the guest cottage is highlighted by warm orange siding and French doors that open onto a wooden deck. Two bright red chairs are positioned outside, complemented by potted plants. A glimpse of the cozy interior is visible through the open doors.

4.94 out of 5 average rating, 741 reviews

Cozy Garden Cottage in the Heart of Richmond

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.

5.0 out of 5 average rating, 123 reviews

Stellar Sellwood Carriage House

4.98 out of 5 average rating, 887 reviews

A shaded patio area is featured, showcasing a set of three wicker chairs with cushions positioned around a small table. A pergola covered in vines provides natural cover, while a landscaped yard and colorful garden shed are visible in the background.

Guesthouse in Woodstock

Woodstock Tiny House

Guesthouses with a patio

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, 276 reviews

Bright, Private & Cozy with Yard

A spacious studio is highlighted by exposed wooden beams overhead. A large bed with neutral bedding occupies one side, while a kitchenette and open shelving are visible on the opposite side. Natural light flows through sliding glass doors, enhancing the airy atmosphere.

5.0 out of 5 average rating, 314 reviews

Finch Studio Cottage in Montavilla, Italy

5.0 out of 5 average rating, 125 reviews

Guesthouse in Mt. Tabor

Mt Tabor Hygge - Comfort Surrounded in Nature

4.97 out of 5 average rating, 182 reviews

An open living area features wooden ceiling beams and large windows that offer views of the surrounding trees. A comfortable sofa sits beside a wooden table. The kitchen area includes modern appliances and white cabinetry, enhancing the space's functionality.

Guesthouse in West Linn

Charming one bedroom apartment in the forest.

4.88 out of 5 average rating, 186 reviews

Mosaic Spa Retreat

Guesthouse in Northeast Portland

A modern kitchen is highlighted by large skylights and sleek wooden accents. Stainless steel appliances complement white cabinetry and a spacious countertop. A dining table with green chairs is positioned in front of a vibrant view through large windows, enhancing natural light throughout the space.

4.98 out of 5 average rating, 103 reviews

Luxury Cabin in the City

The entrance is framed by a wooden awning, showcasing double glass doors. A comfortable chair is positioned to the side, accompanied by decorative pillows. Potted plants adorn the entryway, enhancing the inviting atmosphere of the cottage.

4.92 out of 5 average rating, 123 reviews

City Cottage with Country Feel

4.94 out of 5 average rating, 189 reviews

The Yellow Cottage - Private, Peaceful, & Near PDX

Guest house rentals with a washing machine and dryer

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.

5.0 out of 5 average rating, 240 reviews

Separate spacious guest house over garage.

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, 630 reviews

Little Cedar House Cottage near coffee and shops

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, 686 reviews

Contactless Clean Private Treetop Studio

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.

4.99 out of 5 average rating, 118 reviews

Grandpa's house

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, 804 reviews

Hawthorne Wisteria Retreat

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, 154 reviews

Luxury Loft ~ Bidet, Skylight & Bed for Royalty

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, 250 reviews

Open garden studio in the heart of the SE Portland