Guesthouse vacation 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, 672 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.

4.94 out of 5 average rating, 304 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, 827 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, 549 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.

Guesthouse in Westmoreland

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, 651 reviews

The Westmoreland Lighthouse - Private studio in SE

We've dubbed this stunning, newly constructed 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.

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, 175 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!

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, 210 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 charming guesthouse exterior is framed by lush greenery and colorful flowers. The house features large windows that allow natural light to fill the interior. The welcoming wooden doors add warmth, while a bicycle rests on the pathway, suggesting accessibility to nearby attractions.

5 out of 5 average rating, 261 reviews

Perfectly Portland Clinton St Guesthouse

This light & airy guesthouse is a private retreat in a perfect location, steps from Division St. Walkable to Salt & Straw & local eateries, food carts, and thrift shops. Prepare meals in the fully equipped kitchen or head out by foot to Oma’s Hideaway, a 2022 James Beard Award Finalists. Bring your bicycles to enjoy Clinton St Bike Boulevard or stroll to the Clinton St Theater. The guesthouse is family friendly, having special items to accommodate the littlest of guests.

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, 519 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.

Guesthouse in Foster-Powell

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, 381 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 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.

4.94 out of 5 average rating, 235 reviews

Charming, private 2-level guesthouse-Woodstock

**No list of chores to do at the end of your stay!** Vaulted ceilings, fully private 2 level home. Chef’s kitchen, AC, patio, designer decor and architecture. Contact-less, private self checkin. New Guest House in quiet residential area, upscale Eastmoreland-15 mins from downtown Portland. One bedroom/one bath. Within 10 minutes’ walk is Woodstock Ave-full of cafes, bars, bakeries, and shopping. Ample parking on the street.

Guesthouse in Ladd's Addition

An open living space features modern kitchen cabinetry with an island, complemented by pendant lighting. A cozy sofa adorned with decorative cushions faces a coffee table, with a staircase leading to the upper floor. Natural light streams through the windows, enhancing the bright atmosphere.

5 out of 5 average rating, 123 reviews

Sage Guest House

Enjoy free parking adjacent to the Guest House! Located steps from the Hawthorne District and nestled in the historic Ladd's Addition neighborhood, this guest house is near fine restaurants, coffee shops, entertainment venues, and food carts . Stroll in the shade of century old Elm trees, and discover four public rose gardens located at the compass points within this 1890 neighborhood.

Popular amenities for Southeast Portland guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guesthouse in South Tabor

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, 310 reviews

South Tabor Modern Cottage

4.93 out of 5 average rating, 382 reviews

A light-colored, two-story carriage house is visible, featuring a charming front entrance with blue doors. The spacious outdoor area includes a brick patio and play structures, surrounded by greenery and a wooden fence. A hot tub and vehicle parking area are also present.

Guesthouse in Sunnyside

Find Foodie Bliss from Sunnyside Carriage House

4.94 out of 5 average rating, 905 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

4.94 out of 5 average rating, 316 reviews

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.

Guesthouse in Lents

Sweet SE Studio Cottage

Guesthouse in Westmoreland

The exterior of the cottage is showcased, featuring a bright orange facade and white trim. Two windows are visible on the side, with a glass door that leads to the patio. Surrounding greenery includes tall grasses and various plants, contributing to a natural setting.

4.97 out of 5 average rating, 601 reviews

Dream Cottage! Springwater Bike/Walking Path!

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, 314 reviews

Cozy Clinton Cottage (close-in SE off Division)

A modern guest house entrance is framed by greenery and stone elements. Dual glass doors invite entry, flanked by simple outdoor lighting fixtures. Pebbled paths lead to a garden area, with a few small chairs visible nearby, enhancing the welcoming ambiance of the property.

4.95 out of 5 average rating, 231 reviews

Modern Guest House with Sauna and Gardens

Guesthouse in Ladd's Addition

A compact kitchen area is situated next to a cozy seating space, featuring a black couch with decorative pillows. Modern appliances and cabinetry are visible in the kitchen, and a small dining table with high chairs is positioned nearby. Warm lighting enhances the inviting feel.

4.95 out of 5 average rating, 211 reviews

Portland at your doorstep

Guest house rentals with a patio

4.95 out of 5 average rating, 125 reviews

A serene backyard oasis features a cascading water feature flowing over wooden planks and rocks. The modern tiny home with a dark exterior stands behind an elevated wooden deck, surrounded by lush greenery. Outdoor seating is visible, offering a calm retreat.

Guesthouse in Multnomah

Brand New Tiny Home/Pottery Studio in Cute Village

4.96 out of 5 average rating, 222 reviews

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.

Guesthouse in Lents

Bright, Private & Cozy with Yard

The bathroom features a spacious walk-in shower with dual shower heads and a decorative blue herringbone tile accent wall. A modern sink vanity with dark wood cabinetry is accompanied by a wall-mounted rack displaying white towels. A large mirror is positioned above the sink, reflecting the light.

4.99 out of 5 average rating, 105 reviews

Coda Guesthouse -Now Solar Powered & dog friendly

4.97 out of 5 average rating, 144 reviews

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.

Guesthouse in Sunnyside

The Loft in Hawthorne Tabor

Guesthouse in Laurelhurst

A spacious studio features rich green walls adorned with trailing plants, complemented by wooden beams overhead. A full-sized bed with warm orange bedding invites relaxation, while a cozy seating area and a stylish lamp illuminate the room. Natural light filters through nearby windows.

4.91 out of 5 average rating, 120 reviews

Private city retreat; Cozy Studio w/backyard.

4.98 out of 5 average rating, 224 reviews

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.

Guesthouse in Piedmont

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, 196 reviews

Intimate Casita W/ Hot tub, Movie loft & Chiminea!

Guesthouse in Northeast Portland

An open living area features a modern kitchen with stainless steel appliances and a dining table surrounded by chairs. A cozy seating arrangement includes a yellow chair and blue sofa, with natural light flowing through large windows. Indoor plants add greenery to the space.

4.97 out of 5 average rating, 183 reviews

Beautiful Alberta Guesthouse | Outdoor Soaking Tub

Guest house rentals with a washer and dryer

4.99 out of 5 average rating, 401 reviews

A modern kitchen with light green cabinetry is featured, complemented by open wooden shelving. Stainless steel appliances, including a gas stove, are neatly arranged. Natural light filters through large windows, illuminating the clean white backsplash and countertop.

Guesthouse in Montavilla

Bright Cottage|Vintage Charm|AC|Off Street Parking

4.99 out of 5 average rating, 597 reviews

The living area showcases a bright and airy design, featuring large windows that provide natural light. A plush blue sofa and a dark chair are positioned around a coffee table, while shelves filled with books add character. Art pieces adorn the walls, complemented by greenery.

Guesthouse in King

Spacious Guesthouse with Creative Style and Local Charm

5 out of 5 average rating, 316 reviews

The exterior of a guesthouse is shown, featuring a charming wooden facade and large windows. A private outdoor patio is surrounded by lush greenery, including vibrant plants like a red maple and bamboo. A small round table with wooden chairs invites outdoor relaxation.

Guesthouse in Overlook

Colorful, spacious, light-filled guesthouse on MAX

An open living space features a spacious turquoise couch paired with a wooden coffee table. A dining area with a set of wooden chairs complements the natural light streaming in through large windows. The staircase is highlighted by wood and metal railings, adding modern design elements.

4.96 out of 5 average rating, 235 reviews

Guesthouse Among The Trees with Sauna

4.99 out of 5 average rating, 641 reviews

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.

Guesthouse in Concordia

Contactless Clean Private Treetop Studio

4.99 out of 5 average rating, 219 reviews

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.

Guesthouse in Grant Park

Grant Park Guest House

Guesthouse in Oregon City

A charming red cottage is nestled among lush greenery, with large windows framed in gray. A moss-covered tree stands nearby, adding to the serene woodland setting. Soft light emanates from the cottage's windows, suggesting a cozy atmosphere inside.

5 out of 5 average rating, 603 reviews

Cottage in the Country

A tranquil sleeping area is featured with a spacious bed dressed in crisp white linens and a decorative quilt. Natural wood beams adorn the ceiling, while artwork graces the walls. A doorway leads to an inviting dining area, enhancing the studio's open feel.