Guesthouse holiday rentals in Southeast Portland

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, 750 reviews

Cozy Garden Cottage in the Heart of Richmond

A serene Guest Cottage nestled in a garden and located within walking distance to the local foodie restaurants. You’ll love the location and how quiet it is! The perfect set up for couples, solo travelers or business travel. It's open and bright. French doors, plenty of windows, and skylights to bring in natural light for an open feel. You'll be set up with a comfy mattress, quality linens and plush towels. Nothing more cozy than that! Don't forget about the Smart TV, work desk, and essentials!

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

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!

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!

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, 230 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, 282 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 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

This detached studio home is located in the Woodstock neighborhood, which is one of the few remaining ungentrified areas in Portland. Located a short drive from highway 205 you can get to any part of the city quickly or explore the local bars, restaurants, and parks of SE Portland. There is a private entrance where you can come and go as you please. We're happy to interact with you as little or as much as you prefer, so don't be a stranger or be as private as you like.

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.

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

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, 414 reviews

Bridgetown Bungalow: The perfect cozy getaway!

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, 184 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, 791 reviews

Studio Guesthouse SE Portland

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, 321 reviews

Finch Studio Cottage in Montavilla, Italy

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

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, 352 reviews

Woodstock Farmhouse

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, 112 reviews

Stylish Laurelhurst Guesthouse

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

4.92 out of 5 average rating, 136 reviews

City Cottage with Country Feel

4.88 out of 5 average rating, 188 reviews

Mosaic Spa Retreat

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, 281 reviews

Spacious, bright garden studio on Peninsula Park

4.96 out of 5 average rating, 105 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

4.94 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

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

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

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

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

4.97 out of 5 average rating, 776 reviews

ZEN HAUS. An inner SE Hawthorne/Division Studio.

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, 244 reviews

Separate spacious guest house over garage.

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.