Hilton Head Island waterfront stays

337 waterfront vacation rentals in Hilton Head Island, SC from Whimstay, from $66 a night, each on the water by its own description. Part of our Hilton Head Island coverage.

Rates are each listing's own "from" price on 4 August 2026; the booking page shows live prices and dates. Looking for the houses we would book ourselves? The curated Hilton Head Island list.

Showing 337 to 337 of 337, page 8 of 8. Best rated first, then price.

from $1,392

Stunning oceanfront home with pool, private boardwalk, decks, & elevator

Oceanfront House 6 bed 5 bath sleeps 16

Hilton Head Island, SC

The curated list

Hilton Head Island the way we would book it: a short list of houses we checked for real water access.

Open the Hilton Head Island guide →

Every shore

Ten shores, each with its own stays list and curated picks.

All beach stays →

Affiliate disclosure: Sleep By The Beach earns a commission when you book through Whimstay, Vrbo or Booking.com links on this page, at no extra cost to you. Listing details and photos come from the Whimstay feed and belong to the hosts. How we work.