Portland defies easy summarizing.
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On the one hand, shows like Portlandia have defined the city as a hipster enclave where alternative ways of life abound. On the other hand, the city also has a reputation as Silicon Forest, home to a handful of cutting-edge tech startups and projects.
Still, Portland has a penchant for acceptance. While rising costs and gentrification are challenging the city’s homegrown projects, there remains a stolid dedication to doing things the wackier way—and to great results. Portland, for example, usually lands high on rankings for great food and drinks, for example, along with walkable, safe neighborhoods.
In the case of the latter, you can find dozens of fantastic vacation rentals—many of which embody the city’s dedication to handcrafted quirkiness. Here’s where to find Airbnbs in Portland that are effortlessly cool while still being comfortable.
Airbnbs in Portland that feel effortlessly cool
Yeti’s Treehouse
Yes, you can stay in a treehouse in Portland—one that’s fully covered by trees. This gorgeous one-bedroom treehouse is stilted, putting you up in the bright green canopy. There’s a large deck, along with an outdoor hot tub. Inside, you’ll find designer features throughout, along with a surprising amount of sleeping space that lets you accommodate up to six guests. It’s quirky, it’s well-made, and it’s hiding near Portland’s West Slope neighborhood.
Bigfoot’s Glamping Treehouse
Scratch that—you have more than one treehouse to check out in Portland. This is technically a glamping tent that’s set up on a large landing 12 feet above the ground. You’ll have a perfect indoor-outdoor setup for when the weather is ideal. Just know that this is a bit further from Portland’s center in the Beaverton area, which you can reach in ten minutes by car. Just know that this is a party-free stay for guests aged 15 and over.
The Sneakaway
This beautiful bohemian studio is perfect for long stays and couples’ getaways. There’s a freestanding tub tucked away near the bed, along with a king-sized Tempur-Pedic bed and 15-foot ceilings that make the small space feel grand. The touch of colorful accents and plants give the unit a spa-like feel.
Getaway at Grandma’s
The name says it all. This is a three-bedroom home that’s full of cozy whimsy, a perfect blend of nostalgia from Grandma’s mixed with Portland’s easy-to-see quirky tastes. There’s even a music room with guitars and a synth, in case you’re feeling a little creative. Outside, you can walk to Mount Tabor Park in under five minutes.
Ivon Garden Cottage
This is a guesthouse located in the backyard of the hosts in the highly sought-after Southeast Portland area, close to Division Street. You’ll have your own private entrance and cottage setup that’s just a few blocks from the world-famous Stumptown Coffee. Dozens of other popular restaurants, bars, and shops are also nearby. But you’ll also enjoy your time at home—this is a beautifully crafted cottage with wood features and plenty of natural light.
Onsen Oasis
Looking for a spa-caliber Airbnb in Portland? Welcome to a mini-onsen. This studio has a soaking tub in a lush garden with a cold plunge to boot. Inside, there’s also a freestanding tub with great views from floor-to-ceiling windows. Throughout, you’ll notice a ryokan touch, making this great for anyone who loves Japanese design and tastes.
Historic Craftsman Inner Easts
This gorgeous Craftsman home has two bedrooms and can comfortably fit up to five guests. It’s full of Portland character, from the original artwork in the 1908 home to the All-Clad cookware in the kitchen. It’s both livable and admirable. The location is another key feature—you’re within walking distance to Broadway in the sought-after Sullivan’s Gulch area.
Aqua Star
Check out one of Portland’s quirkiest Airbnbs—a floating home on the Columbia River. The high-design home has a wraparound deck in the back where you can enjoy views of the river. Inside, you’ll find grand rooms with massive windows and upscale features. According to recent reviews, there are spiders on the deck, so arachnophobes aren’t a good fit. That being said, if you don’t mind a few harmless spiders, you’ll be treated to one of the state’s most unique Airbnb stays.
Designer Guesthouse
Here’s another lovely guesthouse where you’ll feel right at home. It’s a one-bedroom that can sleep up to three, just five minutes from Grant Park and a few more minutes from the sought-after Fremont Street. Inside, you’ll find bold design choices that reflect the city’s penchant for picturesque oddities.
Casa Mariposa
Fresh, bright, and comfortable, this one-bedroom comes with a trendy, slightly retro feel. It’s a smaller 400-square-foot guesthouse located in the Brooklyn Park area, close to popular trails like the Springwater Corridor Trail. Despite its small size, there are big amenities that you’ll appreciate, from ultra-fast Wi-Fi to hypoallergenic bedding. Just know that there’s a strict no-smoking policy.
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