Vacation rentals in Portland

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Top-rated vacation rentals in Portland

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Top guest favorite
The living area showcases a light-filled space with polished concrete floors and a cedar tongue-and-groove ceiling. A comfortable sofa and coffee table are arranged on a colorful rug, while a flat-screen TV is positioned against a white wall. Large windows provide views of the outside greenery.
Guest suite in Richmond
4.97 out of 5 average rating, 410 reviews

Walk to Se Division from a Sleek, Architect Designed Space

My wife, Raechel, and I originally designed and built this ADU ( accessory dwelling unit ) with the intention of living there full time, but due to a change of plans, it's available to you. The space was designed by Buckenmeyer Architecture, and was constructed by me. Our space features many unique elements such as: paper-composite counter tops and bathroom tiles, real copper backsplash and bathroom walls, polished concrete floors, cedar tongue and groove ceiling, burnt cedar siding, 16' multi-slide window wall (please open and close slowly), moveable cedar slat screens, custom frosted glass pocket doors, and custom apple-ply kitchen cabinets by George Ramos We love to cook and put great effort into getting the kitchen space dialed in. The kitchen features: bosch speed oven (microwave and convection oven), bosch dishwasher, 2 burner gas range, and Pull-out exhaust and lighting We hope you enjoy the space and neighborhood as much as we do! The guesthouse has it's own separate entrance with a smart lock for convenient self check in. You'll receive the unique code prior to check in. We live in the main house and are available to help make your stay as great as possible. We value your privacy and will not stop by unless contacted. Please text for the quickest response. Nearby Division Steet is known as restaurant row and features some of the best food in Portland, including Pok Pok, Salt and Straw, and Ava Genes. On a warm summer night, there will be hundreds of people just going for a stroll up and down Division. Our guesthouse is a 2 minute walk from a major bus stop, and a Biketown stall where you can rent a bike by the trip. There is no dedicated parking space but there is an abundant amount of non-metered unlimited on-street parking directly in front of our guest house on 28th pl. The Roku Tv enables you to login to your entertainment provider of choice, please remember to logout. The Bose Soundbar is wired to output the TV's audio, but can also be connected to via bluetooth by hitting the bluetooth icon on the Bose remote and pairing with your device. We provide locally roasted coffee beans, a manual conical burr grinder, insulated french press, stovetop kettle, and creamer + sugar. Please enjoy the in-shell Hazelnuts!

Guest favorite
A mid-century living space features high vaulted wood ceilings and large windows that invite natural light. A leather sofa and patterned rug provide comfort, while a kitchen island with bar stools enhances functionality. Artwork adorns the wall, adding a touch of character to the room.
Home in Multnomah
4.96 out of 5 average rating, 123 reviews

Portland Modern

Welcome to our Midcentury Modern – a true masterpiece inspired by the iconic Frank Lloyd Wright. Nestled on a lush 1/3 acre private retreat, this architectural gem is just minutes away from Multnomah Village and Gabriel Park. Immerse yourself in the timeless beauty of this completely renovated mid-mod marvel, where high vaulted open beamed wood ceilings adorn every room on the main floor. This house is perfect for friend groups, families or corporate retreats. Note: 4 bedroom, 2 bath, 2 kitchen.

Top guest favorite
A modern living space features a teal sectional sofa adorned with vibrant throw pillows. A glass coffee table rests atop a textured rug, and the kitchen showcases wooden cabinetry and stainless steel appliances, with natural light enhancing the atmosphere.
Home in Ladd's Addition
5 out of 5 average rating, 217 reviews

New Home Near it All on Division w/ EV Charger

Welcome to The Eloise — a bright, art-filled home centrally-located in the bustling Division/Clinton district of SE Portland. This beautiful ADU has it all. A suite with king bed & bathroom with a luxurious shower; workspace w/ speedy wi-fi; lounge; two TVs a full kitchen, & EV charger. Premium amenities & local treats await you. Tucked into a quiet street just off Division, you’re within walking distance to restaurants, shops, bars, venues, bus & TriMet lines & a 5-minute drive to Downtown.

Top guest favorite
A serene pathway is viewed, meandering through lush greenery. A carved feature rests atop a tree stump on the left side, adding an artistic touch. Sunlight filters through the dense canopy, creating a peaceful and natural atmosphere.
Place to stay in Forest Park
4.97 out of 5 average rating, 102 reviews

Forest Lodge Nature Lookout 15 min to downtown

Cedar Lodge is a chalet cabin lookout on the North summit of Forest Park. Privately located in a wilderness sanctuary only 15 minutes by car to PDX city center & 10 minutes to Linnton, Bethany, Hillsboro and St Johns. Arrive & unwind in an elevated private spa overlooking a forested canyon. Relax with a campfire under stars & towering 300 year old Doug Firs while serenaded with world famous Pacific chorus tree frogs. Then retire to a comfortable night’s sleep, courtesy of a Tuft & Needle bed.

Guest favorite
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
4.98 out of 5 average rating, 217 reviews

Spacious, bright garden studio on Peninsula Park

Explore the world-class restaurants, coffee shops and bars in the nearby Williams and Mississippi districts. Take a stroll around the award winning (and oldest) rose garden in the City of Roses across the street in Peninsula Park. At home, this second story studio has extra space in the meditation loft, a full kitchen, fast internet, and projector for streaming. Enjoy your private deck over the shared garden with hammock and H/C outdoor shower. Bus and train nearby with ample on-street parking.

Top guest favorite
A vintage trailer is nestled beneath a covered patio, offering protection from the elements. Wooden deck steps lead up to the entrance. Potted plants surround the area, and festive string lights add to the inviting ambiance, creating a cozy outdoor space.
Camper/RV in Linnton
4.98 out of 5 average rating, 307 reviews

Cozy vintage camper in the woods of Portland.

Warm & cozy vintage trailer nestled next to Forest Park. Enjoy a fire pit, covered patio, uninterrupted forest vista, and hot, dreamy outdoor bath. Minutes to the center of PDX by car, rideshare, or bus. Comfortable, easy, & whimsical camping experience. Forest Park trail is steps away, Sauvie Island and the historic Cathedral Bridge are 5 minutes by car, and 10 minutes to Slab Town and Alphabet District. The beauty and privacy of this spot may make it hard to venture out. IG: @lilpoppypdx

Guest favorite
A stunning sunset casts vibrant colors across the sky, creating a backdrop for the tiny house built with natural cedar siding. The silhouette of Mt. Hood is visible in the distance, framed by lush greenery and a pathway leading to the entrance.
Tiny home in Sandy
4.96 out of 5 average rating, 1,202 reviews

Mt Hood View Tiny House

Sandy's first and only Tiny House! Although this home is located just a mile from Hwy 26 within Sandy's city limits, it's located on a private 23 acres, so you'll feel completely secluded. This makes it the perfect place to stay while visiting the Mt. Hood area. The tiny house was built to capture the amazing view of Mt. Hood. The home was designed around a moving window wall system that completely opens to the outdoors allowing for one of the best views of Mt. Hood. We hope you enjoy!!!

Top guest favorite
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.
Guesthouse in Arbor Lodge
4.99 out of 5 average rating, 525 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

Top guest favorite
A panoramic view of snow-capped Mt. Hood is framed by open double doors, providing a striking backdrop to the interior. The rustic dining area features wooden chairs and a table, while the floor is set with dark tiles that contrast with the scenic landscape outside.
Apartment in Sandy
4.99 out of 5 average rating, 405 reviews

Gorgeous Mt. Hood View, Ski, Hike or Mt.Bike

Welcome to Sandy Oregon, the Gateway to Mount Hood. This Luxurious cabin-feel home, custom built by top notch craftsman and designer, features breathtaking panoramic views of Mt. Hood and the Sandy River. The view is rated one of the best in the Northwest. Enjoy a glass of wine while sitting by the outdoor fire pit, take a short drive to Timberline Lodge for skiing or snowmobiling, go hiking in the Mt. Hood forest or Mountain Biking at world class "Sandy Ridge". Your options are unlimited!

Guest favorite
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.
Guest suite in Woodlawn
4.97 out of 5 average rating, 603 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.

Top guest favorite
The guest home is set behind a picturesque entrance adorned with an elegant gate and carefully arranged greenery. Paved stone pathways guide visitors through the lush surroundings, leading to the welcoming facade of the home, seamlessly integrated with the tranquil, tree-lined environment.
Guest suite in Portland
5 out of 5 average rating, 527 reviews

IndigoBirch: Luxurious Zen Garden Retreat: Hot Tub

Look no further- as a member of The IndigoBirch Collection™️, our guest home stands as a top-tier experience on Airbnb. Located two blocks away from Reed College, IndigoBirch is nestled on a quiet tree-lined street in the highly desired & historic neighborhood of Eastmoreland. Our location is perfect for the adventurer looking to explore Portland. The guesthouse is two blocks away from public transportation, 12 minute drive to downtown Portland, and 20 minutes to PDX Airport.

Top guest favorite
The entrance to the guesthouse features a warm wooden door framed by lush greenery. Potted plants and a natural wood stool create an inviting atmosphere. Soft string lights hang above, enhancing the serene outdoor space surrounded by trees.
Guesthouse in Woodlawn
4.99 out of 5 average rating, 265 reviews

Sorta Summer House w/ sauna & outdoor shower

The guesthouse is a private oasis in the city. It's surrounded by fruit trees and tall Chinese Mountain bamboo. It's a quick walk to Woodlawn Park, great coffee, a bakery, pizza, whiskey bar, a brewery, seasonal farmers market, and minutes from Alberta Arts District. The airy, open floor plan is filled with natural light, mixed textiles and warm woods. A cedar-surround outdoor shower and private 5x7 Finnish sauna lend to the spa-like setting. Guests say it’s hard to leave!

Popular amenities for Portland vacation rentals

Quick stats about vacation rentals in Portland

  • Total rentals

    6.4K properties

  • Total number of reviews

    589K reviews

  • Family-friendly rentals

    2.7K properties are a good fit for families

  • Pet-friendly rentals

    2.1K properties allow pets

  • Rentals with a pool

    190 properties have a pool

  • Rentals with dedicated workspaces

    3.9K properties have a dedicated workspace

Your guide to Portland

All About Portland

Nestled on the Columbia and Willamette rivers in the shadow of Mount Hood, Portland is an outdoorsy city with plenty of indoor attractions to keep you busy year-round. While the city has a tendency to see more rain than the national average, Oregon’s cultural capital makes up for the grey skies with thriving theater, art, and music scenes, and its impressive dining scene has been the subject of multiple national television shows.

Portland has an eclectic mix of neighborhoods: Downtown and the Pearl District offer higher-end shopping and dining options alongside the city’s iconic independent bookstore; art galleries and indie cinemas are dotted along the Northwest, Hollywood, and Alberta areas; historic architecture abounds in Old Town and Chinatown; and the hip Southeast caters to those looking for vintage finds, record shops, casual eateries, and microbreweries.

On clear days — or if you packed the prerequisite waterproof gear — there are 275 public parks for outdoor exploring, plus the nearby mountains, beaches, and gorges for day trips. Whatever you do, be sure to pop into one of Portland’s famous food cart pods, where you can sample the international cuisine, sip microbrews, and dine alfresco throughout the city.


The best time to stay in a vacation rental in Portland

With its warm weather and lighter than average rainfall from June to August, the city's vibrant outdoor scene really kicks into high gear in summer. These months offer the opportunity to dine and socialize outdoors and a number of exciting festivals also take place during this time. This lovely weather stretches into the early fall months, making September and October great times to visit Portland and spot the changing leaves. The colder rainy season starts in mid-October and stretches through winter into spring, but take a cue from the locals and pack a pair of rain boots and waterproof layers.


Top things to do in Portland

Pittock Mansion

This stunning French Renaissance-style mansion was built in 1914 by a wealthy couple from England who owned Portland’s largest newspaper. Take a guided tour or wander on your own through the 46 period rooms which contain the beautiful antique artwork and furniture collected by the original owners. Outside the main home, there are 40 acres of grounds and other buildings to explore. If you visit around the winter holidays, you’ll find lovely decorations and special events for the whole family.

Portland International Rose Test Garden

Home to over 610 varieties of roses, this garden is the oldest rose test garden in the country. During World War I, roses from around the world were sent here for safekeeping and testing. Today, you’ll find more than 10,000 rose bushes in bloom at peak season between April and October. Check the calendar for all kinds of events throughout the year like classical music performances and plays.

Portland Japanese Garden

The Portland Japanese Garden was created with the purpose of being a symbol of peace between the United States and Japan in the post-World War II realm, and its calming aroma does just that. Spanning 12 acres, you’ll find a cultural village modeled after traditional Japanese architecture that features a waterfall, ponds filled with koi fish, bonsai plants, sand gardens, and a plethora of walking paths. While lovely to visit all year, it’s particularly beautiful in the fall when the leaves change. Stop by the tea house, cafe, and gift shop before you leave.

Frequently Asked Questions

  • How is the weather in Portland?

    Portland has a moderate oceanic climate with cool, rainy winters and warm, dry summers. Average high temperatures in summer are around 80°F (27°C) and in winter, it's usually about 46°F (8°C). Throughout the year, expect regular rainfall, but snow is rare.

  • What are some of the best things to do in Portland?

    In Portland, you can stroll through the serene Lan Su Chinese Garden, explore the food truck scene for diverse culinary experiences, or bike along the Waterfront Park for stunning river views. Visiting the Oregon Museum of Science and Industry is also frequently suggested.

  • What is the best time of year to visit Portland?

    Summer months, between June and August, are often recommended for visiting Portland due to pleasant weather. This time coincides with the Portland Rose Festival, a popular local event that celebrates the city's floral abundance with parades and dragon boat races.

  • What are the best places to stay in Portland?

    Pearl District is a popular area for its art scenes and shopping spots. Alberta Arts District is also often recommended for its vibrant street art and eclectic shops. Northwest District, with its Victorian houses and trendy restaurants, is another area people often choose to stay.

  • What are the best places to visit in Portland?

    Frequently suggested places in Portland include Powell's City of Books, the largest independent new and used bookstore in the world; the International Rose Test Garden with more than 500 varieties of roses; and the Oregon Zoo, known for its conservation efforts.

  • What are some hiking trails in Portland?

    Popular hiking trails in Portland include the Wildwood Trail in Forest Park, which provides a lush, forested escape right in the city, and the challenging Pittock Mansion hike that rewards with panoramic views. The easy, family-friendly hike at Hoyt Arboretum is also often recommended.

  • What are some family activities to do in Portland?

    Families can explore the interactive exhibits at the Oregon Museum of Science and Industry, have fun at the Portland Children's Museum, or enjoy nature at the Portland Japanese Garden. Connecting with native wildlife at the Oregon Zoo is also a popular choice.

  • What are some of the best day trip ideas in Portland?

    Venture out of the city to explore the stunning Columbia River Gorge, about 30 miles (48 km) away, where you can hike the scenic trails or take a drive along the historic Columbia River Highway. Another option is to spend the day in the Willamette Valley, around 50 miles (80 km) south of Portland, renowned for its local food produce and vineyards. If you're a fan of the beach, the charming coastal town of Cannon Beach, about 80 miles (130 km) west, is worth a visit.

  • What types of vacation rentals are available in Portland?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Portland. From over 300 condo rentals, over 2,800 house rentals to over 1,170 apartment rentals, we've got you covered.

  • Are there vacation rentals with a dedicated workspace in Portland?

    Yes! Work meets play with ease at over 3,710 vacation rentals in Portland featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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