Guest house 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, 721 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 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, 332 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.

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.

4.98 out of 5 average rating, 868 reviews

Woodstock Tiny House

Detached, very small (300 sq ft) guest house in the Southeast Portland neighborhood of Woodstock. Lots of walkable eateries as well as New Seasons and Safeway within a 5 minute walk. Close to Reed College, Woodstock Village, Springwater Trail, Southeast Portland Neighborhoods, Public Transportation. You’ll love the location, the outdoors space, and the ambiance. Good for couples, solo adventurers, and business travelers. TV (Netflix enabled!), A/C (summer months), heat, coffee, fridge/freezer.

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, 610 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.

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, 475 reviews

Tabor Cottage: Detached Guest House SE Portland

Mt. Tabor Cottage is a quiet, cozy, detached one bedroom house.with a private, fenced patio. In the South Tabor neighborhood, we are close to Mt. Tabor park and walking distance to several restaurants. It's a 15 minute car ride to the airport or about 17-20 minutes to downtown Portland and only a 5 -7 minute drive to Montavilla, Division St and Hawthorne Blvd restaurants, bars and shopping. Street parking is always available on the block, often next to property or within 150ft, 30 second walk!

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, 194 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 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, 134 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.

The exterior of a two-story guest house showcases a rich burgundy color with contrasting green trim. Wooden support columns frame the entrance, leading to a small set of steps. Large windows allow natural light to illuminate the space, surrounded by a grassy lawn.

4.87 out of 5 average rating, 230 reviews

Modern - Private - AC - Guesthouse

Newly built two story 760 sq. ft. 2bed 1bath guest house! The perfect luxury escape. Some features include zone control heating and air conditioning. A.C. blows cold. Fully stocked kitchen with dishwasher, stove, microwave, fridge, vaulted ceilings, maple hardwood floors, TV with NETFLIX, Comfortable queen beds in each room. Windows offer natural light and views. Quiet neighborhood. The space is a stand alone private guest house with yard. You will love it! Updated faster wifi.

A private outdoor patio is featured, with light green chairs arranged near a welcoming entrance. Paved with stone tiles, the area is surrounded by wooden fencing and greenery, creating a peaceful space for relaxation.

4.95 out of 5 average rating, 448 reviews

Cozy Cottage in Mt. Scott

Welcome to your cozy home base for Portland adventures! This bright studio is fully equipped with everything you need—full kitchen (fridge, stove, oven, microwave, kettle) and a private outdoor patio perfect for relaxing. The open studio layout features a comfy queen bed, walk-in shower, armoire, and a welcoming living area with plenty of natural light. Located near Woodstock and Mt. Scott neighborhoods, you’re close to local favorites, parks, and great food options.

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, 504 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

Guest house in Laurelhurst

A modern kitchen area features white cabinetry and open shelving. A wooden dining table is complemented by sleek white chairs. Natural light enters through large windows, highlighting the clean lines and minimalistic design, while a decorative plant adds a touch of greenery.

4.97 out of 5 average rating, 177 reviews

Modern and Bright Laurelhurst Abode

Our one bedroom cottage is completely private, accessible by a separate walkway, and has an outdoor patio. Extra time was spent choosing finishes and creating a modern, comfortable, and light-filled space. You’ll find everything you need for a weekend in Portland, or a long-term stay. We’ve outfitted a full kitchen, full bathroom with luxurious tub and plush towels, a bedroom with a queen mattress and soft bedding, washer and dryer, and lots of extra touches.

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, 411 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.

Popular amenities for guest house rentals in Southeast Portland

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

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, 111 reviews

Chic Belmont retreat w/tree views & king bed!

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, 190 reviews

Three Wishes Studio

Guest house 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, 432 reviews

Chic Guest House in the Heart of the City

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, 152 reviews

Luxury Loft ~ Bidet, Skylight & Bed for Royalty

4.98 out of 5 average rating, 127 reviews

Coda | Walkable Woodstock Guesthouse | Portland

A bright and welcoming kitchen area features wooden beams overhead and ample natural light from a skylight. A colorful horse-shaped artwork decorates the wall, alongside shelves displaying kitchen items. A small dining table is positioned next to a potted plant, enhancing the inviting atmosphere.

4.92 out of 5 average rating, 200 reviews

Ancillary Dreams

4.88 out of 5 average rating, 177 reviews

SE City Spa Retreat

A warm and inviting studio space features a spacious bed layered with soft linens. Skylights bring in natural light, enhancing the wooden walls and tiled floor. A small dining table with yellow chairs is positioned nearby, alongside a lamp and decorative elements enhancing the cozy ambiance.

4.93 out of 5 average rating, 385 reviews

Treetop Cedar Studio

Guest house rentals with a patio

Guest house in Northeast Portland

A serene studio space features warm wooden walls and vaulted ceilings. A comfortable leather sofa sits on a light carpet. A small dining table with blue chairs is positioned by a large window, offering natural light to the area. A cozy sleeping area is visible in the background.

4.97 out of 5 average rating, 235 reviews

Woodlawn Cottage

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, 115 reviews

Family Friendly SE Portland Getaway w/2 Bedrooms

Guest house 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, 103 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, 262 reviews

Bright, Private & Cozy with Yard

5 out of 5 average rating, 276 reviews

Clinton St Guesthouse • Walkable & Artistic

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, 166 reviews

The Loft in Hawthorne Tabor

Guest house 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, 266 reviews

Spacious, bright garden studio on Peninsula Park

An outdoor courtyard is illuminated by soft lighting, creating a serene evening ambiance. A picnic table and chairs are positioned under a wooden pergola, with a hammock suspended nearby. Lush greenery surrounds the space, enhancing the natural setting.

4.96 out of 5 average rating, 250 reviews

Intimate Casita. Hot-tub, Movie Loft and Chiminea.

Guest house rentals with a washing machine and dryer

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, 735 reviews

Tiny House, Big Charm

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.

4.94 out of 5 average rating, 353 reviews

Sweet SE Studio Cottage

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, 555 reviews

Newly built studio in perfect SE location

4.98 out of 5 average rating, 306 reviews

Private Minimalist Architecture Guesthouse Loft

Guest house in North Portland

A bright bedroom features a spacious bed adorned with soft linens and a light-colored throw. Two bedside tables with lamps flank the bed. Large windows allow natural light to fill the room, with a calming piece of artwork displayed on the wall.

4.97 out of 5 average rating, 236 reviews

Dreamy Modern Overlook ADU

Guest house 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, 673 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, 357 reviews

Woodstock modern apartment

The exterior features a welcoming entrance with a wooden door and modern details. A small patio is furnished with a table and two chairs, surrounded by a wooden fence and colorful autumn leaves. A circular rug adds a pop of color at the entrance.