Long Island

Long Island stretches for about 80 miles, and the first thing that surprises most visitors is how different the two ends feel. In the north, Deadman's Cay and the settlements around it are quiet and practical; in the south, the cliffs near Cape Santa Maria and the long sweep of Cape Santa Maria Beach feel almost cinematic. If you want the island’s signature stop, Dean’s Blue Hole near Clarence Town drops to 663 feet and pulls in divers from around the world. Clarence Town is the place to anchor a first trip. St. Peter and St. Paul Catholic Church sits right by the water, and the nearby Clarence Town Marina is the launch point for boat days, fishing, and diving. For a slower day, head to Hamilton’s Cave, one of the island’s best-known natural sites, then continue to Salt Pond or the Columbus Monument area near the southern end for big views and a sense of how remote this place really is. Food and lodging are spread out, so plan around where you want to spend time rather than expecting one central hub. Stella Maris in the north has a different feel from the Clarence Town and Cape Santa Maria side, and that matters when you’re choosing where to stay. If you want the real Long Island rhythm, rent a car, keep your schedule loose, and build in time for beach stops, roadside fish fry, and long drives with almost no traffic.

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With over 2 million bookable vacation rentals, Vrbo connects homeowners with families and vacationers looking for something more than a hotel for their trip. The Vrbo community offers families an array of rental property types such as condos, cabins, lake rentals, beach houses, and more. Discover properties in destinations that everyone dreams of visiting.

VRBO Vacation Rentals

With over 2 million bookable vacation rentals, Vrbo connects homeowners with families and vacationers looking for something more than a hotel for their trip. The Vrbo community offers families an array of rental property types such as condos, cabins, lake rentals, beach houses, and more. Discover properties in destinations that everyone dreams of visiting.
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