Vacation Rentals with a Pool in Sullivan's Island, Charleston SC

The StayHolyCity Regional Guide

The StayHolyCity Guide to Sullivan's Island

The quiet island

Sullivan's Island is Charleston's best-kept secret hiding in plain sight — a two-mile residential barrier island between the harbor mouth and Isle of Palms, with no hotels, no high-rises, and a single commercial block that closes by 9 p.m. The beach is wide and uncrowded, the streets are canopied by live oaks, and the loudest sound most afternoons is a screen door closing. Edgar Allan Poe was stationed here; the island's literary ghost lingers in the pub that bears his name.

Families love Sullivan's for its gentle waves and the absence of boardwalk chaos. Couples love it for the same reason — plus the fact that The Obstinate Daughter's wood-fired pizzas and natural wines rival anything downtown, without the wait.

History and nature

Fort Moultrie tells the harbor's defense story from the palmetto-log fort that repelled the British in 1776 through the concrete bunkers of WWII — a surprisingly compelling walk-through for all ages. The Sullivan's Island Lighthouse, a modernist triangle built in 1962, is the harbor's most distinctive silhouette and marks the spot where an estimated 40% of enslaved Africans first entered North America.

The beach itself stretches uninterrupted from Breach Inlet to Fort Moultrie — walk it at low tide and you'll have long stretches entirely to yourself, with the Ravenel Bridge framing the western view.

Staying here

Our Sullivan's Island homes are tucked among the live oaks on the island's residential streets — a five-minute walk to the sand, a twenty-minute drive to downtown. Filter by beach front or family-friendly, or join the guest list for first access when calendars open.