Guesthouse holiday rentals in Southeast Portland

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, 156 reviews

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.

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.

4.83 out of 5 average rating, 209 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!

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, 637 reviews

Little Cedar House Cottage near coffee and shops

5 year old detached guest house in Laurelhurst/North Tabor. Bright and spacious with vaulted cedar ceilings. Modern Industrial style with many eco-friendly features such as mini-split heat/ac, tankless water heater, and all-natural fiber area rugs and linens means fewer toxins and a low carbon footprint. Situated near Laurelhurst and Mount Tabor parks with restaurants and amenities nearby. We are also pet friendly and allow well-behaved dogs on leashes for a $30 fee per dog, per visit.

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, 130 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 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.

4.98 out of 5 average rating, 125 reviews

Grandpa's house

Find your perfect Portland retreat in this newly-built guesthouse with contemporary style and deluxe amenities. Ground floor is ADA accessible. Great, central location. Easy access to downtown. Within blocks of some of Portland’s top restaurants, shops, and cafes. Unwind with rain showerheads, heated bathroom floors and slip away under Egyptian cotton sheets. Whether you need rest & relaxation, or a convenient location for your Portland adventures, you’ll find the best of both worlds.

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, 231 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, 698 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 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, 284 reviews

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!

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, 578 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.

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, 423 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.

The living area showcases a comfortable seating arrangement with a spacious sectional sofa and a patterned armchair. A wooden coffee table sits atop a decorative area rug. Natural light filters in through the unique window design, complemented by soft lighting from a floor lamp.

4.98 out of 5 average rating, 269 reviews

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

A cozy studio space features a queen size bed with soft linens, complemented by a plush blue couch and a small coffee table. Natural light enters through windows, while plants and a wall of shelves add a touch of greenery and warmth to the environment.

4.99 out of 5 average rating, 352 reviews

Cozy Clinton Cottage (close-in SE off Division)

Our lovingly renovated, light-filled guest cottage is detached from the main house, with a private entrance and outdoor seating area. Our central location is great for exploring all of the best that Portland has to offer, with easy access to public transit and bike routes. The space is very cozy and has everything you need for a fantastic Portland vacation or work trip.

Popular amenities for Southeast Portland guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

5.0 out of 5 average rating, 287 reviews

Clinton St Guesthouse • Walkable & Artistic

An open living area features a comfortable couch with accent pillows, positioned next to large windows that provide natural light. The adjoining kitchen showcases a modern design with a peninsula and bar stools, surrounded by light wood beams and laminate flooring.

4.99 out of 5 average rating, 359 reviews

South Tabor Modern Cottage

4.98 out of 5 average rating, 895 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

A cozy seating area features two gray armchairs paired with a small round table and a decorative pouf. A wood accent wall complements the space, while a shelf displays books. Lighting from two lamps and a mounted TV adds warmth to the atmosphere.

4.97 out of 5 average rating, 416 reviews

Bridgetown Bungalow: The perfect cozy getaway!

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, 415 reviews

The Loft: Modern Open space in Southeast Portland

An open living area is highlighted by large windows that invite ample natural light. The space features a comfortable couch adorned with yellow and gray cushions, a modern coffee table, and a cozy armchair. The kitchen is seamlessly integrated, showcasing sleek cabinetry and appliances.

4.98 out of 5 average rating, 185 reviews

The Kenilworth Guest House

A spacious studio is presented with a queen-sized bed featuring a patterned duvet. A comfortable sofa is positioned opposite, with stylish decor elements enhancing the ambiance. The room includes an area rug and has a kitchenette visible in the background.

4.91 out of 5 average rating, 792 reviews

Studio Guesthouse SE Portland

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.

4.98 out of 5 average rating, 252 reviews

Eastmoreland Private Guest Suite by Reed College

Guesthouses with a patio

4.98 out of 5 average rating, 138 reviews

Coda | Walkable Woodstock Guesthouse | Portland

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.

4.94 out of 5 average rating, 113 reviews

Stylish Laurelhurst Guesthouse

A charming outdoor patio area features stone flooring accented by vibrant greenery and flowering plants. Soft string lights illuminate the space, creating a cozy ambiance. A private entrance is visible, along with a small hot tub tucked away for relaxation.

4.93 out of 5 average rating, 107 reviews

Château Woodstock – Cozy Stay Near Cafés & Parks

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, 179 reviews

The Loft in Hawthorne Tabor

4.92 out of 5 average rating, 136 reviews

City Cottage with Country Feel

4.88 out of 5 average rating, 189 reviews

Mosaic Spa Retreat

4.96 out of 5 average rating, 108 reviews

Wellness Oasis w/ Sauna, Hot Tub & Fireplace

4.95 out of 5 average rating, 123 reviews

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.

Guesthouse in Woodstock

Family Friendly SE Portland Getaway w/2 Bedrooms

Guest house rentals with a washing machine and dryer

4.97 out of 5 average rating, 776 reviews

ZEN HAUS. An inner SE Hawthorne/Division Studio.

A cozy bedroom is furnished with a spacious bed featuring a patterned duvet cover and two decorative pillows. Natural light filters through two windows, providing a view of the outdoor space. A bedside table holds a lamp and clock, contributing to the serene ambiance.

4.96 out of 5 average rating, 246 reviews

Sellwood Detached Apartment

4.94 out of 5 average rating, 268 reviews

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.

Guesthouse in Woodstock

Charming, private 2-level guesthouse-Woodstock

A cozy living area is highlighted by a spacious blue sofa adorned with patterned cushions. Neutral lamps provide soft lighting, while large windows reveal a view of the outdoor patio. A stylish wooden coffee table with a geometric centerpiece rests on a patterned rug.

4.96 out of 5 average rating, 615 reviews

Taylor Street Cottage

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, 811 reviews

Hawthorne Wisteria Retreat

Guesthouse in Northeast Portland

A comfortable living area features a light-colored leather couch adorned with various textured pillows. A rustic wooden coffee table sits in front, decorated with a floral arrangement. A patterned artwork and a framed photograph decorate the walls, enhancing the stylish ambiance.

4.94 out of 5 average rating, 183 reviews

Pet Friendly, Cozy & Curated Designer Guesthouse

A cottage entrance is framed by vibrant flower beds featuring pink and red blooms. A pathway leads to a white double door, flanked by lush greenery. Natural light brightens the scene, with a hint of soft landscaping visible along the sides.

4.95 out of 5 average rating, 372 reviews

Sweet SE Studio Cottage

The exterior of a detached cottage is depicted, featuring a blue-grey facade and a dark front door. A pathway of concrete leads to the entrance, flanked by greenery. Two blue Adirondack chairs are positioned on a gravel area nearby, enhancing the cozy outdoor setting.