1,331 Portland Vacation Rentals & Short Term Rentals

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Compare Portland vacation rentals from 10 rental sites including HomeAway, Booking.com, TripAdvisor and more, ranging from $29 to $99999999 a night.

Information about Portland

About Portland

Portland is a rapidly growing, well-loved city located at the confluence of the Columbia and Willamette rivers near the Washington and Oregon border. A mecca for outdoor enthusiasts, foodies, and artists alike, Portland is a culturally rich city that has become an increasingly popular travel destination in recent years. “Stumptown,” as some call it, hosts a wealth of events that you are sure to enjoy, including the world renowned Portland Rose Festival and Christmas Ship Parade. Known for its thriving hipster culture, as well being eco-friendly and safe, Portland is the ideal place to start exploring the Pacific Northwest.

Portland Neighborhoods

The most densely populated and popular neighborhood in the metro area is the Northwest. This corner of the city boasts art galleries, Chinatown, celebrated restaurants, and the much sought after Pearl District. Other popular areas include the Northeast, which hosts the historic Hollywood District and is home to the Portland Trail Blazers basketball team. The local farm-laden Southeast is another point of interest, sitting atop Mt. Tabor, the city’s dormant volcano.

Things to do in Portland

From exploring high-quality local food and craft beers to participating in countless outdoor activities, Portland has something for everyone. You can start off your day taking a stroll in Washington Park, which hosts a children’s museum, zoo, Japanese tea garden, International Rose Test Garden, arboretum, and forestry discovery museum. Relax and recharge at one of the local coffee shops, bakeries, or brewhouses before heading to the famous Saturday Market to shop for local artisan arts and crafts. Experience Oregon’s natural beauty with a kayak trip on the Willamette River or a hike through Forest Park. Keep an eye out for gourmet food trucks! Portland tends to have pop-up outdoor food, music, and art venues during the summer.

Portland Accommodations

Your stay in Portland will be off to a good start as soon as you arrive at Portland International Airport, named “Best Airport in America” by Travel + Leisure. The convenient and affordable TriMet public transportation system services all of the metro Portland area through light rail, streetcars, and buses. You can even skateboard into town along one of the designated routes! From floating homes to trendy urban apartments, Tripping offers the full range of Portland experiences. It’s yours for the choosing!

Best Neighborhoods to Stay in When You Visit Portland

Downtown

From the beautiful parks to the various festivals that happen throughout the year, Downtown has no shortage of opportunities to help visitors enjoy this beautiful city. In the heart of Downtown, Pioneer Courthouse Square hosts activities all year long, such as farmer’s markets and free concerts. Head down to the Tom McCall Waterfront Park, where you can enjoy jogging and biking or just relax and enjoy the fountain there.

Pearl District

Highly walkable and bustling with activity, the Pearl District is quintessentially Portland. Take a brewery tour through this former warehouse district to see the birthplace of Portland beer. This upscale neighborhood also features some of Portland’s most delicious food, including the upscale Mediterranean Exploration Company. And, of course, no trip to the Pearl District would be complete without a visit to Powell’s City of Books, the largest new and used bookstore in the world.

Alberta Arts District

This diverse area is known for its art, culminating in a street fair on the last Thursday of each month. Stroll the streets to find boutique shops and galleries. The famous ice cream restaurant Salt & Straw lives here—be sure to try one of their unique flavors after an afternoon exploring this funky district. You can even have dinner and a drink at McMenamin’s Kennedy School, a 100-year-old schoolhouse that was transformed into a restaurant.

Things to do in Downtown

Though Portland is a bustling city with over 600,000 residents, there is green space aplenty in this Pacific Northwestern haven. Washington Park exemplifies how a city can be both urban and verdant, featuring a zoo, several museums, and the International Rose Test Garden. Stately and snow-capped, Mount Hood looks on as visitors explore the various gardens and the World Forestry Center, a hands-on museum that introduces guests to forests in Oregon and around the world.

For a unique way to immerse yourself in the city, try a scavenger hunt! Families, groups, and individuals alike are guided through the city to discover landmarks as well as learn about Portland’s history. Blend in with the locals by renting a bike, which is both a fun and functional means of transportation here.

Despite grungy fashion and hordes of “hipsters,” Portland is home to some delicious dining options. Just in Downtown, options for cuisine and price range are dizzying. The Heathman Restaurant, located on Broadway, prepares French dishes from Pacific Northwest ingredients. Go up to the Portland City Grill, 30 floors above the city, for a huge menu and unbeatable views.

Vacation Rentals in Portland

Find the best Portland vacation rentals with Tripping.com. Choose from 1361 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $29 a night to $99999999 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 1007 of homes in Portland offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 198 rentals with pool or jacuzzi, or relax with the family in one of the 807 homes with cable TV.

For all those dog lovers and cat lovers, Portland offers 280 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 10 rental sites in Portland where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 666 HomeAway rentals, 259 Booking.com short term rentals and 216 TripAdvisor vacation rentals.