Built in 1927 and originally known as Pickering's Pleasure Pier, this Pacific Beach landmark once housed a carnival midway and the short-lived Crystal Ballroom before the first overnight cottages were added in 1930. The Allen family has owned the property since 1961, and general manager Julie Neal—who first worked the pier in the 1990s—returned in 2021 to lead operations heading into the pier's approaching centennial. Twenty-nine Cape Cod-style cottages sit directly on the wooden pier over the Pacific Ocean, each with a full kitchen, a separate living room and bedroom, a private deck, and a dedicated parking spot at the pier entrance. Guests who have never been on a board can book a session with Pacific Beach Surf School, which sets up on the sand directly below the cottages each morning. The property has drawn its share of Hollywood attention over the years: scenes from the 1989 film Night Rain were shot on location, the 1990s television series Renegade starring Lorenzo Lamas filmed here, and actor Pierce Brosnan stayed in one of the cottages during production of The Heist. There are no restaurants, bars, or resort-style amenities on the pier itself—just the cottages, an office, a gift shop, and the ocean. When the public gate closes each evening, overnight guests have the pier to themselves, a level of seclusion that does not exist at any other lodging property in San Diego. Neal has noted in interviews that some families have been booking the same cottage for fifty consecutive years, and a walk off the pier puts guests directly onto the boardwalk near Costa Brava and other waterfront restaurants within a two-minute stroll. Seasonal minimum-night requirements apply during peak months, and the cottages book out well in advance, so early reservations are a practical necessity rather than a suggestion. The 4.6-star Google rating across 650-plus reviews reflects a property where the experience, not the thread count, is the entire point.