Holiday rentals in Portland

4.82 out of 5 average rating, 536 reviews

Treehouse in Portland

Yeti's Tree House: Where Dreams Come True

"Thank you for creating such a magical place..." Recent Guest "Best Tree House I've ever seen!" Recent Guest Let the kid in you come to play in this real treehouse held up by four trees, 18 feet off the ground. Zip line down or take a giant soaking tub. A magical stroll through the woods leads to the suspension bridge. You won't believe you're only minutes from town. Wear appropriate shoes as it is a short 2-minute hike to the tree house. At times, it can get a little slick.

A comfortable living area features a light-colored leather couch adorned with various textured pillows. A rustic wooden coffee table sits in front, decorated with a floral arrangement. A patterned artwork and a framed photograph decorate the walls, enhancing the stylish ambiance.

4.94 out of 5 average rating, 178 reviews

Pet Friendly, Cozy & Curated Designer Guesthouse

Our guesthouse is situated behind our home, located on a large corner lot in beautiful Grant Park. Surrounded by picturesque homes and tree-canopied streets, it’s a perfect combination of peace and quiet alongside accessibility. Dozens of local shops and fabulous PDX restaurants, just a 10 minute walk away. Five minutes to freeway access, guests enjoy convenient options, exclusive privacy, and detailed designer touches. A perfect base camp for an extended PNW exploration, or a weekend getaway!

Home in Northeast Portland

The open living area features vaulted wooden beams and large windows allowing natural light. A comfortable sofa and a pair of armchairs surround a coffee table on a colorful rug. In the background, the modern kitchen is visible, with sleek cabinetry and stainless steel appliances.

5.0 out of 5 average rating, 116 reviews

Modern Home — Prime Alberta Arts

This new home is steps from lively Alberta Street, the heart of NE Portland. It's perfect for couples, business travelers, and anyone looking to explore Northeast, Portland's best neighborhood. Plush king-size bed, open kitchen and living room, 1.5 bathrooms, and private yard. Explore awesome restaurants, bars, and shops around the corner, while staying on a quiet residential street. This home is just 15 minutes from the airport, and close to downtown (transit friendly!). Hablamos español.

A detached entrance is seen with a wooden door and large windows, framed by a clean gray exterior. A small patio area features a table and two chairs, inviting relaxation. The surrounding landscape includes gravel and low-maintenance plants, enhancing a sense of privacy.

5.0 out of 5 average rating, 121 reviews

Private urban retreat, new build, 1bedroom, sleep4

Relax in this calm, clean and simple space. Enter in from the sidewalk fence to a little patio great for enjoying your coffee and some fresh air. There is a full kitchen that opens into the living area with a skylight and high windows that offer great natural light. Walk down the hall and enjoy the spacious bathroom with our provided bath tray for real relaxation. Tuck yourself into bed and enjoy the stars or choose to black out windows using our automated shades for uninterrupted sleep.

Guest house in North Portland

The exterior of the home is highlighted by contemporary design elements and a clean white facade. A flowering tree adds a touch of color, while large glass doors invite natural light into the living area. Surrounding landscaping is thoughtfully arranged with minimalistic plantings.

4.99 out of 5 average rating, 577 reviews

Accessible, AIA-Award Winning, Urban Garden Oasis

A nurturing place with abundant light, garden views, & access to the best Portland food. “The best Airbnb I’ve ever stayed in!” - frequent guest comment. - American Institute of Architects Award to designer Webster Wilson - Upscale amenities & European fixtures - Quiet NoPo neighborhood tree-lined street, minutes from downtown - Fully equipped kitchen w/ fresh local coffee - Indoor & outdoor dining - See photo captions for more details - Trained Service Animals welcome; no pets nor ESAs

5.0 out of 5 average rating, 124 reviews

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.

Guest house in Portland

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!

Guest suite in Northeast Portland

An open studio layout is highlighted by an inviting soaking tub surrounded by plants. Light-colored walls enhance the airy feel, while warm wooden elements, like a platform bed and cabinetry, provide a harmonious balance. A cozy seating area and kitchen are subtly integrated.

4.97 out of 5 average rating, 656 reviews

The Sneakaway

Built to feel like a little touch of luxury, with the quaintness and quality of a craft home. This place is a true sneak-away with a two person soaking tub, marble shower, king tempurpedic bed and a fully stocked kitchen. This open studio has 15 ft ceilings allowing ample sunlight and a large, light feeling. This house was designed and built by me my friends so no detail is overlooked or unintentional. This was our labor of love for a year and Im so excited to now be able to share it.

A modern kitchen is highlighted by large skylights and sleek wooden accents. Stainless steel appliances complement white cabinetry and a spacious countertop. A dining table with green chairs is positioned in front of a vibrant view through large windows, enhancing natural light throughout the space.

4.98 out of 5 average rating, 105 reviews

Luxury Cabin in the City

Modern cabin in the city built from the ground up for peace and serenity! Giant skylights abound to make even the dreariest of days feel special, and if the sun is out there's no better spot in all of Portland to experience it! Join friends and family at Irving park for a picnic or a tennis match. Or, hop over to Williams and Mississippi for some of the best known restaurants in Portland. Very close to the convention and Moda center that give you tremendous options for entertainment.

Guest house in North Portland

The cottage exterior is nestled within lush greenery, featuring a textured, light-colored stucco façade and a distinctive triangular roof. Surrounding plants and stones create a serene landscape, complemented by wooden steps leading to the entrance, enhancing the inviting and private atmosphere.

4.97 out of 5 average rating, 467 reviews

The Green Door PDX: A European Inspired Cottage.

A bolthole created from passion by Kaemingk Collection, The Green Door PDX was designed to provide a unique respite from the energy of Portland while being conveniently located only minutes from downtown and popular shopping/eating districts. We have taken queues from Europe and built a traditional field cottage tucked into the landscape at the front of the property and surrounded it with mature greenery for an inviting welcome and ultimate privacy for our guests.

4.98 out of 5 average rating, 199 reviews

A spacious backyard is surrounded by lush greenery and tall trees, offering an unobstructed view of the distant mountains. A stone fire pit is positioned on a well-maintained lawn, enhancing the tranquil outdoor space. The clear sky and natural landscape create a serene atmosphere.

Guest suite in Gresham

Breathtaking views, Fish, Ski, Mt. Bike, or Hike

Experience a charming two-bedroom suite in the daylight basement of a two-story home, complete with a private entrance and covered patio. Enjoy breathtaking views of Mt. Hood and the Sandy River from your beautiful backyard. Nestled near Oxbow Park, you're just minutes from shops, restaurants, and outdoor adventures in the Columbia River Gorge and beyond. With the Portland airport only 25 minutes away, this cozy retreat is the perfect getaway!

4.99 out of 5 average rating, 476 reviews

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.

Home in Portland

Modern Guesthouse in Portland's Central Eastside

Tall ceilings, an open staircase and walls of windows flood the space with light (even in Portland), while molded plywood Eames chairs add mid-century style. Located in the heart of Portland within walking distance to great restaurants, coffee and parks. Fast, gigabit fiber internet, full kitchen, large table, and private outdoor spaces help maximize your stay and comfort, whether you're alone or with a group. Editor's pick in Dwell.

The spacious interior features tall ceilings and an open layout. A comfortable seating area with a blue couch sits near a bright window. The well-equipped kitchen and dining space are visible, alongside a sleeping area with neatly rolled towels on the bed.

4.91 out of 5 average rating, 682 reviews

Luxe Garden Cottage in Central PDX

✦ Beautiful new guest cottage located in the Historic Irvington neighborhood. ✦ Located a mere 6-10 minutes from downtown. ✦ Tall ceilings and gorgeous A-Frame house ✦Walk, bike or drive to the many cafes, shops and restaurants at nearby destination neighborhoods, including Alberta Arts District (1.5 miles), Broadway, (.5 miles) Williams District (.9 miles), Mississippi Ave. (1.5 miles)

Popular amenities for Portland holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Portland

Flat in Southwest Portland

The spacious living area features large windows that allow natural light to fill the room. A stylish seating arrangement is complemented by an accent chair and a coffee table, all set atop a decorative rug. A fireplace adds warmth to the inviting ambiance.

4.98 out of 5 average rating, 178 reviews

Mid-Century Hillsdale Retreat

4.86 out of 5 average rating, 900 reviews

A private hot tub glows in vibrant green, positioned in the foreground. The tranquil outdoor area is surrounded by soft lighting, highlighting the entrance to the cozy Casita and its inviting seating arrangement, creating a peaceful evening retreat.

Guest house in Woodstock

Romantic Casita. Hot Tub, Firepit. Pets Welcome!

4.88 out of 5 average rating, 239 reviews

The interior space features warm wood finishes and large windows allowing natural light to fill the area. A compact kitchen area is equipped with essential appliances, and a comfortable seating arrangement includes a reclining chair and a small table. A spiral staircase leads to the lofted sleeping area.

Treehouse in Mt. Tabor

Mt Tabor Tree House, Hidden Urban Retreat

Luxe

Home in Portland

4.78 out of 5 average rating, 23 reviews

Aqua Star – Iconic Floating Home on the Columbia

Home in Southwest Portland

An airy dining area is illuminated by natural light from large windows, showcasing views of the surrounding landscape. A modern table with chairs is positioned near the window, while stylish bar stools line the kitchen counter, offering a subtle separation between spaces.

4.95 out of 5 average rating, 65 reviews

Serene Forest Retreat mins to Downtown

Guest suite in Southwest Portland

A spacious deck features a round table surrounded by four chairs. The view captures a vibrant sunset over the Portland skyline, with a blend of city buildings and natural greenery in the foreground. The sky displays hues of orange, pink, and gray.

4.98 out of 5 average rating, 52 reviews

Magnificent finishes and views!

Flat in Northeast Portland

5.0 out of 5 average rating, 14 reviews

Kerns Studio Near Coffee, Dining & Transit