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Best Vacation Rentals in Portland, Oregon
Our highest-rated homes, loved by thousands of guests
94 matching properties
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Portland Favorite
Guest Approved
Portland's BestAbout Best Stays
These are our best vacation rentals in Portland — the homes guests rave about, rebook year after year, and recommend to their friends. Every property on this page has earned consistently high ratings from real guests, with thoughtful design, premium amenities, and locations in Portland's most desirable neighborhoods.
What makes a Portland vacation rental 'the best' isn't just thread count and square footage — it's the details that make your stay feel effortless. Fast WiFi that actually works for video calls. A kitchen stocked with real cookware, not just the basics. A location where you can walk to coffee, dinner, and a park without getting in a car. These homes deliver on all of that.
Our top-rated properties span every Portland neighborhood and style — from modern Pearl District lofts to craftsman bungalows in Hawthorne, spacious family homes in Alberta, and sleek townhomes in the Mississippi District. What they all share is a standard of quality that turns first-time visitors into repeat guests.
Frequently Asked Questions
How do you determine the 'best' vacation rentals?
Our top-rated collection features properties with consistently high guest reviews (4.8+ stars), premium amenities, thoughtful design, and prime locations. These are the homes that guests rebook and recommend most often.
Are the best Portland vacation rentals more expensive?
Not necessarily. While our luxury collection tends to be at the higher end, many of our top-rated homes are priced competitively. Great design and a perfect location don't always come with a premium price tag — especially when you book direct and skip the platform fees.
What neighborhoods have the best vacation rentals?
Our highest-rated properties are spread across Portland's top neighborhoods: Hawthorne-Belmont, Alberta Arts District, Pearl District, Mississippi, NW 23rd, and Sellwood-Moreland. Each offers a unique Portland experience with walkable dining, shopping, and parks.