Sleeps 8+ stays in Hilton Head Island
103 sleeps eight or more rentals in Hilton Head Island, SC, from $98 a night.
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 97 to 103 of 103, page 3 of 3. Best rated first, then price.
Charming Waterfront Getaway with Seasonal Pool & Hot Tub, Tennis, Beach Access
Waterfront
Condo
3 bed
3 bath
sleeps 9
Hilton Head Island, SC
Luxury Direct Oceanfront 3BR Panoramic Ocean Views
Oceanfront
Villa
3 bed
3 bath
sleeps 10
Hilton Head Island, SC
Stunning Oceanfront Hideaway with Private Pool, Deck, and Yard - Dogs Welcome
Oceanfront
House
5 bed
4 bath
sleeps 14
pets ok
Hilton Head Island, SC
Beachfront beauty with pool access fireplaces, jetted tub, balconies, & WD
Beachfront
House
5 bed
5 bath
sleeps 10
Hilton Head Island, SC
Ocean and Marsh View Home with private pool, dog friendly, beachfront
Beachfront
House
6 bed
6 bath
sleeps 16
pets ok
Hilton Head Island, SC
Beachfront home with private pool, expansive deck & breathtaking views
Beachfront
House
5 bed
4 bath
sleeps 12
pets ok
Hilton Head Island, SC
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 →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.