2 Best Hotels in Tenderloin, San Francisco

Inside the magnificent, flatiron-shape Beaux Arts–style building is one of the city's most spectacular places to stay, a sharp, upscale, ultra-hip boutique hotel; in contrast, outside is one of the roughest intersections for street life in San Francisco. The Proper rates high both for the eye-catching redesign by Kelly Wearstler (she also designed the guest room blankets and kimonos) and for amenities like SF's premier rooftop bar (Charmaine's) and Bellino fine Italian linens, towels, and down comforters.

Recently rebranded as part of Hilton's boutique Curio Collection, this art-driven hotel draws creatives and tech workers with its effortlessly chic design, central location, and rooftop bar. Tiny local artworks composed of found wood, metal, clay, and moss lead into the white-washed, high-ceilinged registration area; more art awaits around the corner in the modern but comfortable lobby, done in white, light blue, and gray. Oversize windows onto city views dominate the roomy guest rooms—soothing in earth tones and blues with exposed-cement touches—which come equipped with 55-inch LED TVs, high-speed Wi-Fi, Grind-brand Nespresso machines, and fun local art accents. Bathrooms have vertical tiles in green hues and walk-in showers (suites have deep soaking tubs); Cowshed bath products, robes, and slippers come standard. On street level, Spoke Coffee & Cafe offers morning coffee and light meals, and rooftop bar Rise Over Run draws a trendy crowd.