Smathers Beach offers the most convenient beach experience in Key West. It’s easy to find, has plenty of parking, and offers shade, tables, and the widest stretch of sand on the island. Located on the south side of the island, you can easily find this beach by driving along South Roosevelt Blvd, which is the southern perimeter road of Key West. You can park right on the street next to the beach, along a mile-plus stretch. There’s a public restroom, and a few vendors parked near the beach, selling shaved ice, seashells, and other beach-related treats and baubles.
If you’re biking, lock up at any of the bike racks along the sidewalk in several spots along the road. A row of cute palm trees separates the dune area of the beach from the sidewalk, providing a nice backdrop for pictures of your Key West vacation. The other side of South Roosevelt is lined with condos and hotels, and vacationers staying at these properties can be seen dragging beach chairs, coolers, and towels across the road all day long, so drive slowly in this area.
The most popular vacation rentals along Smathers Beach would probably be the condos at La Brisa. Many of these units offer ocean views, covered parking, and great location at the western end of South Roosevelt Blvd. This end is closer to the Casa Marina area and Old Town. They are condos, so of course if you rent them as Key West vacation rentals you get full kitchen, bathrooms, living rooms, all furnished and ready to go.