House holiday rentals in Southeast Portland

A charming cottage exterior is framed by lush greenery and a gravel pathway. The house features a gabled roof, large front windows allowing ample natural light, and a welcoming entryway flanked by wooden fences, creating an inviting atmosphere.

4.96 out of 5 average rating, 444 reviews

Market Street Guesthouse PDX

This is THE ONE! A perfect blend of upscale finishes, fixtures, and appliances in a beautiful and welcoming cottage. Soaring ceilings welcome the weary traveler into a space that offers fine linens, a fully stocked kitchen, two full baths with heated tile floors and a custom, versatile layout. No expense was spared building the space: the vibe is true Pacific NW, with wood trim, warmth and beauty all around. IDEAL walkable location smack dab amongst Portland's coolest neighborhood amenities!

4.96 out of 5 average rating, 281 reviews

Mount Tabor Hideaway

Mt Tabor Hideaway is a fully stand-alone guesthouse at the back of our lot. Located at the foot of Mt Tabor, near SE Division & 60th. Enjoy privacy & comfort in its bright, modern & clean space. 2 BR with 3/4 Ba on each level, full kitchen, heat & A/C. French doors lead to your private outdoor patio. Reliable high speed internet, 600 mbps. Small smart TV. Enjoy a misty morning, drizzly afternoon or evening walk in Mt Tabor Park in a friendly neighborhood. City permit # 18–1 37613–0 00–00 – HO

A spacious living area features a leather sofa facing a fireplace. A large piece of artwork adorns the wall above a mid-century modern console, surrounded by green plants. Natural light floods in through glass doors, creating an inviting atmosphere.

4.89 out of 5 average rating, 123 reviews

Epic record collection & hot tub in bright home

Close to Willamette River waterfront trails. Two blocks from Ladds Rose Gardens, Clinton Street (several cool bars, patios, Loyly spa, and theater!) and Division Street - home to some of the city's best restaurants — Ava Gene, Omas, Fairweather, Quaintrelle, and more. My home is good for couples, solo adventurers, business travelers, and families. Enjoy the extensive record collection (old blues, rock, and jazz), relax in the covered outdoor patio and spa, and enjoy the well stocked kitchen.

4.87 out of 5 average rating, 199 reviews

A cozy living area is presented, featuring a comfortable sofa and a stylish desk with a chair. A sleek TV is mounted on the wall opposite a fireplace, providing warmth. Large windows offer natural light, with a decorative rug enhancing the inviting ambiance.

Home in Ladd's Addition

Cozy Bungalow in Ladd’s Addition • Walk/Dine/Shop

Welcome to “Happy Place”, your cozy retreat that feels like a home-away-from-home in the vibrant heart of Portland! Our sanctuary in the bustling SE Clinton/Division area offers fast internet, perfect for work-from-home needs, and is a short stroll from top restaurants, bars, and boutiques. Boasting a walkability score of 92, city exploration is a breeze. Ideal for foodies, culture lovers, and outdoor adventurers, we provide FREE on-site parking and embrace the spirit of Portland living.

A spacious living area features a light grey sectional sofa adorned with red and white cushions. A glass coffee table sits on a soft area rug, while a low television console displays decorative items. Large windows provide natural light, revealing a view of greenery outside.

4.95 out of 5 average rating, 149 reviews

The Plex PDX

Live Like a Local! The Plex will immerse you in mid century style and vintage charm with privacy and modern comforts-all in the heart of Portland. Sip coffee on the patio while you plan your adventures. Eat, drink, and play in this walkable central neighborhood. Just a few blocks from destination casual and upscale dining, coffee shops, boutiques, and historic Laurelhurst Park and Theater. Perfect for up to 4 people with driveway parking and a garage to store bikes and other gear.

4.82 out of 5 average rating, 102 reviews

Heart of Hawthorne! Newly Remodeled, 99 Walk Score

✨ Charming 1907 Home Steps from Hawthorne Blvd ✨ 🌇 Walk score 99 — bars, restaurants & shops steps away 🛏️ 2 bedrooms, 3 beds, sleeps 6 comfortably 🍳 Full kitchen with dishwasher & stainless appliances 🛋️ Smart TV, fast WiFi & laptop workspace 👶 Pack ’n Play available by advance request (not stored onsite), kid-friendly & extended stays welcome ❄️ AC & heating for year-round comfort 🔒 Private entrance & driveway for 2 cars 🍽️ Less than 2 min walk to Hawthorne's best.

4.96 out of 5 average rating, 271 reviews

Holiday Home

Welcome to Portland! We hope you have a wonderful time in our beautiful city, and that Holiday Home makes it feel like yours for a while. It's cozy and spacious, with 7 distinct outdoor seating areas for groups of any size — gather together, or peel off for a quieter conversation without anyone feeling left out. After 8 years and 267 stays, this house still surprises people: it's a current Guest Favorite, in the top 10% of homes on Airbnb.

4.94 out of 5 average rating, 236 reviews

Midcentury Modern - Backyard Oasis with Grill

Experience comfort and style in this 3-bedroom mid-century modern Airbnb in NE Portland, perfect for families, groups, or business travelers. Enjoy fast Wi-Fi, a dedicated workspace, and a fully equipped kitchen for easy home-cooked meals. Relax with backyard BBQs or explore Mount Tabor Park, local breweries. With top dining spots and attractions just minutes away, enjoy a relaxing and stylish Portland stay that feels just like home.

4.86 out of 5 average rating, 273 reviews

3 BR 1 BA - Cozy Home - Walkscore 97 - Shopping

Stay at this top-rated Airbnb in Southeast Portland near the Hawthorne and Belmont districts. This stylish 3-bedroom, 1-bath pet-friendly vacation rental offers a full kitchen, cozy living space, and modern amenities. Walk to iconic cafes, bars, vintage shops, and parks. Ideal for families, couples, or friends looking to explore Portland’s top attractions while enjoying comfort and convenience in a prime walkable location.

4.81 out of 5 average rating, 318 reviews

Bright + Walkable | Vintage Hawthorne Charm

✨ Bright Hawthorne 1BR Apartment in Vintage House ✨ 🏠 Private Apartment 2 in the main blue house 🛏️ Cozy 1-bedroom retreat for 2 guests 🍳 Full kitchen with dishwasher & dining table 🐾 Pet-friendly 💻 Laptop-friendly workspace & fast WiFi 🧺 Shared basement laundry ❄️ Mini-split A/C & heat for year-round comfort 🍽️ Steps from Hawthorne cafes, restaurants, shops, groceries, and bars. Free street parking.

5.0 out of 5 average rating, 160 reviews

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.

Home in Ladd's Addition

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.

A spacious living area features a green sectional sofa adorned with various colorful pillows. A round glass coffee table sits at the center, surrounded by a vibrant area rug. A hand-painted mural of cranes decorates the wall, complementing the natural light from large windows.

4.9 out of 5 average rating, 314 reviews

Portland Regency Moderne - an Artist’s Home

Maximalism meets jungalow glam in our best expression of modern Hollywood Regency for the Rose City. Hand-painted cranes and geometric tropical boho murals, alongside gilded and colorful decor, adorn this centrally-located, mid-century-ranch artist’s home. Private access to 2BR/1BA home, includes a full kitchen, dining area, and sunset views of the West Hills from the front deck.

Popular amenities for Southeast Portland house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area is highlighted by a warm brown leather seating arrangement, including two armchairs and a three-seat sofa. Natural light filters through the dual windows with rolled shades, complemented by two potted plants and a contemporary area rug.

4.99 out of 5 average rating, 117 reviews

Corner of Heaven

4.96 out of 5 average rating, 181 reviews

Home in Vancouver

The Starburst Inn: Enclosed Heated Pool, Theater

4.97 out of 5 average rating, 179 reviews

An airy kitchen features sloped ceilings with wooden beams and warm wood cabinetry. A vintage-style aqua refrigerator complements stainless steel appliances. Natural light filters through three windows, while a vibrant rug adds a pop of color to the space.

Home in North Portland

Rose City Hideaway

A charming Craftsman home is set against a vibrant blue sky, featuring a well-maintained garden filled with colorful flowers. The entrance is framed by lush greenery and a small set of steps leads to the welcoming front porch.

4.91 out of 5 average rating, 69 reviews

Frankie's Place; Walkable Craftsman luxury!

5.0 out of 5 average rating, 41 reviews

A heated in-ground pool is surrounded by a concrete patio, featuring a slide on one end. Lush greenery and vibrant flowers are visible nearby, creating an inviting outdoor space. A covered deck area with seating is seen in the background, providing shade and relaxation options.

Home in Vancouver

5bdrm,Heated Pool, Hot Tub, Sauna.

4.73 out of 5 average rating, 94 reviews

Home in Milwaukie

Private Pool & Hot Tub Oasis | Cowboy Retreat

4.88 out of 5 average rating, 24 reviews

A two-story home with a light grey exterior and dark blue shutters is featured, showcasing a welcoming front porch. The entrance is highlighted by a circular window and a decorative front door. Lush green lawns and well-maintained landscaping give a serene appearance.

Home in Beaverton

Swim Spa + Hot Tub, Gazebo, BBQ Grill, 6 Bedrooms

5.0 out of 5 average rating, 22 reviews

Home in Cedar Hills

Modern 3-Story Gem | Across from Nike | 1GB Wi-Fi

Weekly house rentals

A well-lit studio features a spacious bed with a patterned duvet. A cozy blue couch and a decorative rug are included in the seating area. Soft textile and natural hues create a calm environment, complemented by a floor lamp for additional lighting.

4.94 out of 5 average rating, 421 reviews

Mt Tabor House Salmon Room

A modern kitchen features sleek white cabinetry and natural wood accents. Stainless steel appliances are included, along with a spacious island at the center, which has stools for seating. Natural light filters in through a large window, brightening the inviting space.

4.95 out of 5 average rating, 343 reviews

The Clinton Modern

4.79 out of 5 average rating, 952 reviews

Bright 3BR/2BA | Steps to Hawthorne | 5 Beds

4.83 out of 5 average rating, 121 reviews

Private & Cozy Mt. Tabor House - Centrally Located

A spacious living area features a leather sofa and two wooden chairs positioned around a glass coffee table. Natural light enters through the windows, enhancing the warm wood floors and the bright red area rug. A decorative fireplace and plants contribute to the inviting ambiance.

4.99 out of 5 average rating, 136 reviews

Spacious Southeast Craftsman - WFH Bliss

4.89 out of 5 average rating, 526 reviews

Mid-Century Dream | 3BR/2BA | Heart of Hawthorne

4.96 out of 5 average rating, 140 reviews

Live Like a Local in Artful Craftsman by Division

A modern living area features a brown leather couch with red and white cushions, paired with a circular coffee table. Colorful artwork adorns the walls, and an arcade game cabinet adds a playful touch. The open layout includes a kitchenette in the background.

4.88 out of 5 average rating, 146 reviews

Beautiful Portland Gem Minutes from Mt. Tabor

Private house rentals

The cottage's inviting front porch is framed by lush greenery and colorful blooms. A pathway leads to the entrance, with a cozy chair positioned to one side. The surrounding landscaping features a mix of plants and shrubs, creating a welcoming atmosphere.

4.99 out of 5 average rating, 164 reviews

Heron Cottage, Urban Retreat-King Bed

An open living space features a stylish wooden staircase, enhancing the flow of natural light. A modern dining table is accompanied by Arne Jacobsen Ant dining chairs. Decorative plants and a round mirror add a touch of elegance, while large glass doors provide a view of the outdoor area.

4.99 out of 5 average rating, 479 reviews

Modern Guesthouse in Portland's Central Eastside

A spacious studio apartment is highlighted with a patterned blue comforter covering the pull-out couch and spacious bed. Kitchen cabinetry, a dining table, and a TV are visible in the background. Natural light fills the room, creating a relaxed ambiance.

4.87 out of 5 average rating, 205 reviews

Clean and Beautiful Inner SE Apartment

The living room is furnished with a black leather couch and two matching armchairs, arranged around a wooden coffee table. Natural light floods in through new windows, highlighting the decorative fireplace and a large flat-screen TV mounted above. An adjacent dining area features a classic chandelier and a wooden dining table.

4.86 out of 5 average rating, 534 reviews

Walkable Portland Escape for Groups

A landscaped garden area is shaded by a large tree, featuring lush green foliage and a variety of plants. A stone birdbath is visible among the greenery. Comfortable outdoor seating can be seen in the background, inviting relaxation amidst the vibrant surroundings.

4.9 out of 5 average rating, 296 reviews

Tabor Retreat

A bright living room features two comfortable sofas, one in leather and the other in a warm fabric, positioned around a wooden coffee table. Natural light flows through large windows, illuminating the room's intricate ceiling details and decorative accents.

4.99 out of 5 average rating, 287 reviews

Restored Buckman Craftsman-your perfect home base`

4.97 out of 5 average rating, 154 reviews

Home in Ladd's Addition

4BR/3BA Penthouse | Balcony | Foodie District

A comfortable living area features two blue armchairs positioned beside a wooden coffee table. A textured rug lies underfoot, while a modern painting is displayed above a stone fireplace. Built-in shelves hold a collection of books and a small potted plant adds a touch of greenery.