Four blocks from Duval Street along Truman Avenue (which also happens to be the last stretch of 2,369-mile interstate U.S. 1), this quaint, low-key bed-and-breakfast occupies a handsome yellow-and-white Classic Revival manse built in 1891 by a bigwig in Key West’s once powerful cigar-making industry. Restored in the early 1990s, it’s been owned for the past 18 years by Monica Wiemer and Jamie Rodriguez. It’s unpretentious and casual, with friendly, attentive staff and a mix of period-style furnishings, rattan, florals, and “Tommy-Bahama tropical.” The rectangular pool out back is great—and clothing-optional. A couple of caveats: You won’t find some in-room amenities many of us have come to expect, such as a TV. Truman is Old Town’s other main street, and while not hustling and bustling like Duval, traffic’s certainly heavier than on side streets, so if noise is an issue, request a non-front-facing room. Even given all that, if you’re looking for affordability, La Pensione is a pleasant pick indeed.