No, you cannot legally sleep on the beach in Key West. The city has strict municipal ordinances that prohibit camping, lodging, or sleeping on public beaches, parks, or streets between the hours of 11:00 PM and sunrise. This includes popular spots like Smathers Beach, Higgs Beach, and Fort Zachary Taylor Historic State Park. Key West is a small, high-traffic island with limited public space, and local law enforcement actively patrols the beaches at night to enforce these rules. If you are caught sleeping on the beach, you may be asked to move along, issued a citation, or even arrested in cases of repeated offenses. While the idea of sleeping under the stars next to the ocean sounds romantic, it is also a safety concern due to the lack of facilities and potential for changing tides. For those looking for a "natural" experience, there are several designated campgrounds on the nearby Stock Island or further up the Florida Keys (like Boyd’s Key West Campground), but within the city limits of Key West itself, you must stay in a licensed hotel, guesthouse, or registered campsite to avoid legal trouble.