Sleeps 8+ stays in Hilton Head Island
114 sleeps eight or more rentals around 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 114 of 114, page 3 of 3. Best rated first, then price.
Upgraded condo on waterfront with pool, hot tub, & tennis access - near beach
Oceanfront Villa with Ocean Views, Shared Pool Hot Tub, and Nearby Beach Access
Oceanfront Villa with Shared Pools, Hot tub, and Beach Access
Newly-renovated ocean front condo on the 5th floor with a private balcony
Waterfront Getaway with Pools, Hot Tub, and Views of the Atlantic Ocean
Oceanfront with Views! Pool & Beach on Hilton Head
Oceanfront Villa! Private Beach, Pool, Hilton Head
Beachfront escape with pools, hot tub, athletic courts, WD, and central AC
Renovated Sea Pines Home Near Beach
Endless Tides - Marshfront Lands End Retreat. Pool Across Street. 500 Feet to Beach Access
Oceanfront Villa with kitchen, balcony, patio shared pool and trails
Charming Waterfront Getaway with Seasonal Pool & Hot Tub, Tennis, Beach Access
See Hilton Head Island on Vrbo, with dates and live prices.
Search Vrbo → Booking.com → Affiliate links.Luxury Direct Oceanfront 3BR Panoramic Ocean Views
Stunning Oceanfront Hideaway with Private Pool, Deck, and Yard - Dogs Welcome
Beachfront beauty with pool access fireplaces, jetted tub, balconies, & WD
Ocean and Marsh View Home with private pool, dog friendly, beachfront
Beachfront home with private pool, expansive deck & breathtaking views
Stunning oceanfront home with pool, private boardwalk, decks, & elevator
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.