Holiday houses in Southeast Portland

Apartment in Ladd's Addition

The exterior of a historic home showcases its charming pink facade and large front porch. Lush greenery frames the entrance, with well-maintained shrubs and a pathway leading to the front steps. The inviting atmosphere reflects the character of the neighborhood.

Charming Classic Ladd's/Hawthorne Gem/Sleeps 4

You will stay in an historic neighborhood with 100 year old trees, in a home with character and beauty fitting of this lovely, walkable and friendly part of Portland called Ladd's Addition, where it intersects with Hawthorne Blvd. Steps from restaurants, food carts, pubs, coffee houses, bike rentals, a comedy club and more! Vintage shopping? Yes. Easy public transit? Yes. You can also spend time relaxing;there is a modern kitchen, living and dining room, and even a piano if you like to play.

FamilyValueAccuracy

4.88 out of 5 average rating, 514 reviews

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!

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4.91 out of 5 average rating, 159 reviews

A modern bathroom is featured with a deep soaking tub and sleek wood vanity. A round mirror and stylish light fixtures provide illumination. Neutral-toned tiles add warmth to the space, while a small plant decorates the bathtub area.

Home in Portland

Hawthorne House - A+ Location! Pet Friendly!

Killer location!! An ez 2 min walk down the street from Hawthorne/Division in SE Portland! Enjoy the best restaurants, shops, bars PDX offers! Centrally located in great neighborhood! Main floor unit w/private access! Self check in! Bright and airy living spaces! Fully equipped kitchen for preparing delicious meals. Full sized wash/dryer. High speed Wi-Fi. Cozy bedroom w/plush queen-sized bed. Clean and modern bathroom stocked w/essentials. I'm excited to host you during your visit to PDX!!

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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, 131 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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4.98 out of 5 average rating, 482 reviews

A charming exterior of a single-story home is surrounded by lush green lawn and colorful flower beds. Large windows allow natural light to fill the interior. A welcoming front entrance features a classic door beneath a small overhang.

Apartment in Portland

Elegant SE Portland/Reed College BLUE MOON SUITE

The Blue Moon Suite is a cool, comfortable and convenient apartment within a home to stay if you're visiting Reed College, are in Portland for business (downtown is only 15 mins away) or if you are just touring the city. We look forward to welcoming you into our home and aim to make your stay as comfortable as possible while taking your privacy seriously & offering private access to an elegantly decorated yet comfortable one bedroom lower level apartment with everything that you might need.

FamilyValueQuiet

4.98 out of 5 average rating, 635 reviews

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.

Guesthouse in Woodstock

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 patio located behind the Airbnb. As an added bonus, breakfast items and home baked treats are provided.

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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, 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.

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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, 579 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, 183 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, 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.

FamilyValueLayout

4.91 out of 5 average rating, 407 reviews

A modern living area is presented with a light gray sofa adorned with patterned cushions. A wooden coffee table sits in front, while the open kitchen and dining area are visible in the background, featuring a dining table and various appliances.

Apartment in Woodstock

Clean, Bright & Quiet 2 Bed apt. Pets Welcome!

Welcome to a calm & open space to relax while you explore Portland. A new purposed planned apartment that is full of original art, murals, amenities and peaceful design features. We LOVE your pets & welcome them to stay with you! Each pet is $25 per reservation. The Light house is near great restaurants, fun Portland neighborhood bars, ice-cream parlors, famous Portland food cart scenes, boutique supermarkets, parks & much much more.

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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

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Popular amenities for Southeast Portland holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Southeast Portland

4.96 out of 5 average rating, 564 reviews

A cozy seating area features a double futon and a plush chair in a warm-toned room. Natural light filters through a nearby window, drawing attention to the potted plant and textured wall behind the seating. Soft carpet enhances the inviting space.

Guest suite in Mt. Tabor

Luxurious Cape Cod in Central Eastside

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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, 210 reviews

Private Oasis! Cozy & Close to Everything!

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A spacious living area features a gray sofa accompanied by a wooden coffee table, set on a neutral rug. Large windows invite natural light, while a pair of doors opens to a green garden. Soft lighting is provided by a lamp beside the sofa.

4.98 out of 5 average rating, 715 reviews

Ivon Garden Cottage

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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, 231 reviews

Willow Tree Guesthouse

LocationValueLong stay

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

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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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4.98 out of 5 average rating, 100 reviews

A spacious living room features a light-colored sofa and armchair arranged around a wooden coffee table. Potted plants add greenery, while bookshelves and a sideboard provide storage. Soft, natural light filters through the windows, illuminating the warm tones of the area rug.

Guest suite in Woodstock

Private Garden Apartment in Woodstock Neighborhood

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