Guesthouse holiday rentals in Southeast Portland

5.0 out of 5 average rating, 286 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.

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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, 251 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!

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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, 206 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!

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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, 635 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.

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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, 125 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!

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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, 227 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!

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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, 696 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.

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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, 575 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.

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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, 178 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

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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, 420 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.

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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, 109 reviews

Stylish Laurelhurst Guesthouse

Filled with natural light, centrally located guest house in the upscale neighborhood of Laurelhurst in NE Portland. A short walk to beautiful Laurelhurst Park and minutes on bike or car to all Portland has to offer. Our newly built guest house has everything a traveler would want with private patio & parking right in front. Stay cool in the summer and toasty in the winter with the newly installed mini split system.

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The kitchen features navy blue cabinetry paired with white countertops and a farmhouse sink. Shelves display glassware and flower arrangements, while a gas stove adds functionality. A microwave is housed within the cabinetry, and a colorful rug provides a warm touch to the space.

4.98 out of 5 average rating, 138 reviews

Walkable Guesthouse - Inner SE Portland

Private one bedroom ADU in the walkable SE Division and Clinton neighborhood. Second story unit with queen bed (firm mattress) walk-in shower, and easy access to shops, food, and parks. Parents and grandparents return often for the quiet setting. The backyard sitting area is not included in the rental. There are two small dogs on the property, but they do not have access to the guest pathway.

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Popular amenities for Southeast Portland guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

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, 356 reviews

South Tabor Modern Cottage

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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, 181 reviews

The Kenilworth Guest House

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4.98 out of 5 average rating, 891 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

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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

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4.93 out of 5 average rating, 442 reviews

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

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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, 787 reviews

Studio Guesthouse SE Portland

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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, 410 reviews

The Loft: Modern Open space in Southeast Portland

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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, 350 reviews

Woodstock Farmhouse

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Guesthouses with a patio

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, 102 reviews

Château Woodstock – Cozy Stay Near Cafés & Parks

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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.

4.91 out of 5 average rating, 128 reviews

City Cottage with Country Feel

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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, 108 reviews

Luxury Cabin in the City

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4.94 out of 5 average rating, 192 reviews

The Yellow Cottage - Private, Peaceful, & Near PDX

ValueFamilyIndoor spaces

4.88 out of 5 average rating, 187 reviews

Mosaic Spa Retreat

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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

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5.0 out of 5 average rating, 127 reviews

Guesthouse in Mt. Tabor

Mt Tabor Hygge - Comfort Surrounded in Nature

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4.96 out of 5 average rating, 104 reviews

Wellness Oasis w/ Sauna, Hot Tub & Fireplace

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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.

4.95 out of 5 average rating, 442 reviews

Chic Guest House in the Heart of the City

ValueFamilyAir conditioning

4.97 out of 5 average rating, 774 reviews

ZEN HAUS. An inner SE Hawthorne/Division Studio.

LocationFamilyQuiet

4.94 out of 5 average rating, 265 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

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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, 122 reviews

Grandpa's house

ValueLocationIndoor spaces

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, 807 reviews

Hawthorne Wisteria Retreat

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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.

4.96 out of 5 average rating, 490 reviews

Tabor Cottage: Detached Guest House SE Portland

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A welcoming entrance to a private home is framed by lush greenery and colorful flowers. The wooden steps lead up to a white door, flanked by a large window. Natural light bathes the area, emphasizing the inviting ambiance of the space.

4.97 out of 5 average rating, 117 reviews

Lovely Northeast Portland Oasis

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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.