Vacation rentals in Pearl District, Portland

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Top-rated vacation rentals in Pearl District, Portland

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Superhost

A spacious living area is highlighted by tall windows, allowing natural light to cascade in. A cozy seating arrangement surrounds a central fireplace, with a dining table positioned nearby. Vibrant green plants add a touch of nature, complementing the wood-beamed ceiling.

Home in Northeast Portland

4.95 out of 5 average rating, 312 reviews

The Portland Villa on Alberta St

In the heart of NE Portland's vibrant and bustling Alberta Arts district. Endless options for dining, drinking, shopping and entertainment within walking distance. The main home is 2800 sqft plus an additional 1200 sqft on a private rooftop deck (that we built ourselves!). There is natural light (and plants) galore. Prepare meals in our chef’s kitchen. We don’t skimp on linens, supplies, cozy mattresses or bedding. A legally permitted rental by the City of Portland. 1% for The Planet member.

Superhost

A private patio area is featured, showcasing a wooden structure with clear roofing, surrounded by lush greenery. Two chairs with cushions are positioned near a small table, creating an inviting space for relaxation amidst flowering plants.

Home in Central Northeast Portland

4.98 out of 5 average rating, 104 reviews

Heron Cottage, Urban Retreat-King Bed

The Heron Cottage was built in 1914 and was part of a network of small farms that existed in what was then the hinderlands of Portland. Now it's an urban vest pocket neighborhood with easy access to a regional hospital, light rail, bus routes and freeways. This is a pedestrian neighborhood with very narrow streets. We know our neighbors and enjoy the cultural diversity of this little enclave. The cottage's front porch beckons you to slow down, relax and maybe even make some new friends.

Superhost

A well-lit upper hallway leads to a cozy bedroom, featuring sloped ceilings. Artwork hangs on the wall, while a wooden chair and bedside table accompany a spacious bed adorned with light bedding. Natural light enters through an adjacent window.

Home in Sherwood

4.99 out of 5 average rating, 144 reviews

Old Town Retreat - Best place in Old Town Sherwood

At the gateway to wine country, our peaceful Old Town 1916 craftsman home brings historical charm with many amenities right in the heart of Old Town Sherwood. Sleeps 9 with 6 new beds, 2.5 remodeled baths and an open kitchen with gas range, everything you need for a few or many. Owner occupies the basement and rear separated dwelling on property. However, both the basement and rear dwelling are completely locked off and have entirely separate entrances. The best place in town.

Superhost

A bright living area is highlighted by large windows and natural light. A sectional sofa is paired with a glass coffee table, while a plush bench provides additional seating. Decorative elements include a houseplant and wall accents, contributing to a spacious and modern feel.

Home in Northeast Portland

4.9 out of 5 average rating, 333 reviews

Huge Home with King Beds in Prime Spot with Views!

Architectural masterpiece on a safe, quiet street just blocks from Williams and Mississippi Ave, home to some of Portland’s best dining, drinking, shopping and more. Spread out across three spacious levels with multiple living areas, a large open kitchen with two eating bars, four king bedrooms and a bunk room (each with its own TV!), and 3.5 bathrooms. Relax and dine alfresco on the beautiful back patio, then watch sunrises and sunsets from the east and west facing roof decks!

Superhost

An illuminated patio area features a covered wooden structure with string lights providing a warm glow. Comfortable seating is arranged around a central table, and a large umbrella adds color to the outdoor space. Lush plants are visible along the perimeter, enhancing the tranquil atmosphere.

Cottage in Beaverton

4.93 out of 5 average rating, 105 reviews

Cozy Cooper Mtn Cottage

Uniquely cozy with all the amenities of home but in a cottage up on Cooper Mt. Where you are surrounded by trees , feel the breezes, sunrise and sunset in the same day, and sometimes the wonderful wildlife around us. Birds in the sky , rabbits and sometimes deer, and yes our two friendly goats. Oh yes and the expansive midnight sky with the bright stars twinkling above or the big round moon shining down on you as you sit on the patio in the evening enjoying the night air.

Superhost

The kitchen features stainless steel appliances, including a gas range and microwave, with a butcher block island and concrete countertops. Open shelving displays dishware, while a dining area is set with wooden stools and a table topped with a bowl of fruit and a bottle of wine.

Guesthouse in North Portland

5 out of 5 average rating, 222 reviews

Richmond Cottage in St Johns, Portland

This light, bright cottage is located in the heart of the St Johns neighborhood in Portland. Full of charm it features loads of reclaimed wood with an industrial farmhouse vibe. Complete with a private deck, keyless entry, full kitchen with eat-in island and a sleeping loft with a queen sized bed. It is a close walk to restaurants, coffee shops, bars and shopping. Easy access to downtown Portland, University of Portland, the airport and the rest that Portland has to offer.

Superhost

An airy living space featuring a modern design with a large sectional sofa and a dining table. A circular light fixture hangs above the table. The double French doors open to a patio, while a 65” Smart TV is visible on a clean white media console.

Home in Laurelhurst

4.95 out of 5 average rating, 329 reviews

❤️ CLEAN ★ LUXURY OASIS ★ NEAR DOWNTOWN

☀ 10 Mins to downtown + Airport ☀ Free Private on-site parking ☀ Luxury queen bed • premium bedding ☀ Queen sleeper sofa in living room ☀ Fully stocked cook’s kitchen ☀ Large private patio ☀ Fire Pit + Gas BBQ ☀ Super Fast Wifi • USB charging outlets ☀ 65” 4K Smart TV ☀ Smart Home • Alexa equipped ☀ Nebia Spa shower ☀ Heated floors ☀ Steps from public transit ☀ Safe walkable neighborhood ☀ Bikes to explore Portland ★☆Learn More Below & Experience Portland With Us!★☆

Superhost

Home in Vancouver

4.76 out of 5 average rating, 188 reviews

Style Meets Comfort in Beautiful Design

Discover unparalleled comfort and style in this beautifully designed Vancouver retreat, perfect for families and groups seeking a memorable getaway. This spacious home hosts two living rooms, king-sized beds in every bedroom, and a fully equipped kitchen, this is where comfort meets convenience. Nestled in a peaceful neighborhood with easy access to local attractions, dining, and shopping, making it the ideal home base for your Pacific Northwest exploration.

Superhost

Apartment in Northeast Portland

4.92 out of 5 average rating, 133 reviews

The White House in Mississippi ~ 95 WalkScore

Welcome to our charming three-bedroom retreat in the heart of Mississippi Street! Step outside and dive into the vibrant local scene, with endless dining, shopping, and entertainment options just steps away. After a fun-filled day exploring, return to unwind in style with a massive 4K HDTV, a fully equipped kitchen, and comfortable memory foam mattresses in all three bedrooms. Discover the best of Mississippi Street from our perfectly situated apartment!

Superhost

The exterior of the loft house features a sleek design with modern wooden accents. Sliding glass doors provide access to the indoor space. A small outdoor seating area with chairs is complemented by a stone pathway and a planter, enhancing the inviting atmosphere of the backyard.

Guesthouse in Central Northeast Portland

4.99 out of 5 average rating, 471 reviews

LoftHousePDX w/ Sauna & Hot Tub

Debuted during Portland's Accessory Dwelling Tour, “Loft House PDX” is centrally located just off beautiful Alameda Ridge. Business and leisure travelers alike will find a peaceful retreat awaiting them in this tastefully-appointed, open and airy, modern loft house with all the accoutrements one might wish for—including a Finlandia Sauna, and STIL hot tub to enjoy after a long day of work or play, and a custom gas firepit for evening lounging...

Superhost

A spacious open-concept living area is visible, featuring vaulted ceilings and large windows that provide natural light. The kitchen, equipped with modern appliances, is complemented by a dining area with bar stools. A cozy seating arrangement surrounds a coffee table, with a flat-screen TV and gas fireplace enhancing the ambiance.

Guesthouse in North Portland

5 out of 5 average rating, 105 reviews

Overlook Cottage, Upscale 2 bedroom and 2 bath

Be our guest in a newly completed two bedroom two bath cottage designed specifically for short term stays and complemented with designer finishes and décor. Located in Portland’s historic Overlook neighborhood; a short walk to light rail transit, Overlook Park, and Mississippi Street boutique shops and restaurants. We strive to provide a welcoming and hospitable environment with strict cleaning protocols.

Superhost

A bright and airy room features large windows and soft curtains, allowing natural light to fill the space. A spacious bed is complemented by floral wallpaper. A small dining area with a chair is present, alongside a modern kitchen countertop and a view of the private patio through French doors.

Apartment in Portland

4.82 out of 5 average rating, 121 reviews

La Petite- BRAND NEW!

ELEGANT URBAN OASIS IN PORTLAND'S DIVISION NEIGHBORHOOD. Step into an enclave of opulence and comfort in our newly designed Accessory Dwelling Unit (ADU). This private haven, sculpted with attention to every detail, stands as a testament to luxury and comfort, offering you Portland's finest in an intimate, and sleek setting. You'll cherish our ADU's tranquil ambiance and our foodie forward neighborhood.

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What guests are saying

Cascade Park Cottage

5 out of 5 average rating, 79 reviews4 days ago

Our stay was truly a dream from start to finish. The home was warm, welcoming, and filled with so many thoughtful touches—from the charming decor to the little surprises like toys in the loft that made our kiddo feel right at home. It was such a treat for our whole family. Even the snacks were a lifesaver—especially while juggling a busy toddler adjusting to a new space. It’s those kinds of details that show just how much care the hosts put into every corner of the experience. They were always kind, responsive, and ready to help with anything we needed. We felt so taken care of the entire time. We couldn’t recommend their home more!

Guesthouse in Vancouver

What guests are saying

Charming apartment in the middle of Portland!

4.95 out of 5 average rating, 92 reviews3 weeks ago

Enjoyed the visit here. Place was spacious and well stocked. Walked one day to a fantastic local coffee shop, another to the closer McDonalds and Starbucks as it was raining. I would definitely stay again on future Portland visit. Only downside was there is no TV - we ended ip with 3 adults crowded around a MacBook to watch opening day baseball. This was 100% my fault as when I checked listing it was noted specifically at bottom there is no tv.

Apartment in Portland

What guests are saying

Lovely Backyard Oasis

5 out of 5 average rating, 12 reviews3 days ago

This little trailer was absolutely so cozy and delightful. I loved waking up to hearing some rain on it one morning of my stay. The shower had great pressure and warmed up really quick. The location was really close to lots of different things. Rebecca even had a lovely little binder full of recommendations of places to look at and visit. All in all I had a delightful stay and would definitely visit here again.

Guesthouse in North Portland

What guests are saying

Enchanting Cottage in Woodstock

4.85 out of 5 average rating, 13 reviews3 months ago

This is a great place! I love the neighborhood. Everyone was friendly and the area was well-kept. There’s a lovely park next to the school at the end of the street. Amazingly quiet yet walkable to grocery, restaurants, etc. The yard is very cool, wish we could have enjoyed it more due to it being winter. Inside we were very comfortable. Had a special holiday meal with our daughter and the kitchen was up to the task. Everything was clean and comfy. We hope to return!

Guest suite in Woodstock

What guests are saying

PNW Woodland Escape | Fire Pit , BBQ+ Views!

4.95 out of 5 average rating, 58 reviews2 weeks ago

We stayed at this cozy cabin for a girls weekend getaway and had the best time! The cabin was spotless — so clean and comfortable, with everything we needed to relax and enjoy our trip. Echo was incredibly friendly and welcoming, and truly went above and beyond to make sure we had a great experience. Echo was even so gracious as to help us retrieve an item left behind. Highly recommend this place for anyone looking for a peaceful retreat with amazing hospitality. I would definitely come back!

Cabin in Beaverton

What guests are saying

{Lake Front Fun} The Little Cottage on West Bay

4.9 out of 5 average rating, 21 reviews4 months ago

This is a unique locale. It has the best equipped kitchen and supplies we have ever experienced in an Airbnb. We loved the decor of the kitchen like a cute 1950s diner. The shower was great. We visited in winter so we couldn’t take advantage of the wonderful water’s-edge outdoor living space. Jen is a great and instant communicator. We recommend you visit her!

Guesthouse in Lake Grove

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