Southwest Hills Short Term Rentals combine skyline views with nature trails, making them ideal for stylish, short urban escapes.
For travelers who want a quieter side of Portland—one with tree-lined streets, hilltop views, and architecturally rich homes—Southwest Hills is where refinement meets rest. Just minutes from downtown, this residential neighborhood feels miles away from the rush, offering a more elevated take on the short-term stay.
Southwest Hills short term rentals are curated escapes. Whether you’re staying for a few nights or a few weeks, they offer space, light, and the kind of calm that turns a trip into a recharge. Here’s where to stay when you’re seeking sophistication that still feels like home.
Short-Term Rentals Near Council Crest Park Offer Views and Total Calm
At the highest point in Portland, Council Crest Park gives you a 180-degree sweep of city, mountains, and sky. Staying nearby means easy access to wooded trails, quiet mornings, and evenings that end with a skyline glow.
Southwest Hills short term rentals around this area are designed for tranquility. Expect hillside decks, oversized windows, and a sense of elevation—both literal and emotional. It’s a perfect match for travelers who want nature without losing touch with the city.
Stay Along Fairmount Boulevard for Elegant Homes With Character
Fairmount Boulevard wraps around the hillside in a quiet loop of historic charm. The homes here range from mid-century gems to timeless estates, often with lush gardens and sweeping paths.
These Southwest Hills short term rentals offer the kind of character you can’t replicate—vaulted ceilings, hardwood floors, and thoughtful details that make the space feel lived-in yet elevated. Great for guests who want atmosphere, walkability, and access to Marquam Nature Park nearby.
Choose the Area Around Patton Road for Quick Access to Downtown With Privacy
Patton Road is a strategic spot—high enough for peace, low enough for access. From here, you’re minutes from downtown Portland, OHSU, and Washington Park, all while being tucked into a hillside setting that feels private and serene.
Southwest Hills short term rentals in this pocket work well for professionals, creatives, and long-weekend travelers. The balance of location and quiet is rare—and exactly what makes this area stand out.
Look Near Portland Heights for Classic Luxury and Neighborhood Views
Portland Heights is where traditional architecture meets established elegance. Think manicured lawns, multi-level homes, and views that span the city.
Staying here means coming home to stately interiors, formal dining spaces, and the kind of neighborhood walk that makes you want to linger. These Southwest Hills short term rentals are best suited for guests who appreciate space, privacy, and a strong sense of place.
Stay South of Dosch Road for Modern Rentals Surrounded by Forested Stillness
For a newer take on the Southwest Hills aesthetic, look to the forested sections south of Dosch Road. These rentals are modern in layout—open floor plans, big windows, and minimalist finishes—with nature always within view.
Southwest Hills short term rentals in this zone are ideal for longer stays, remote workers, or anyone who wants to step off the map without stepping too far from the city. Surrounded by trees and light, they offer that rare Portland mix: deep calm with total design clarity.
Quiet Luxury, Portland Style
Southwest Hills offers the kind of stay you don’t usually expect in a city—quiet, scenic, and deeply refined. It’s not about being close to everything. It’s about being close to what matters: comfort, light, and a space that lets you exhale.
Southwest Hills short term rentals are for travelers who want substance with their style. Explore more urban retreats with Casai—where every stay is elevated, intentional, and just a little off the usual path.
