Hilton Head Island waterfront stays

357 waterfront vacation rentals around Hilton Head Island, SC from Whimstay, from $66 a night. Every one is on the water by its own description: beachfront, gulf front, bayfront, canal front or lakefront.

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 357 of 357, page 8 of 8. Best rated first, then price.

Hilton Head Island waterfront stays

Waterfront Getaway with Pools, Hot Tub, and Views of the Atlantic Ocean

Oceanfront condo with pools, hot tubs, fitness room, & central AC

Stunning oceanfront villa with WiFi, pool & hot tub, private balcony

Oceanfront with Views! Pool & Beach on Hilton Head

51 Ocean Club

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

Sunlit Oceanfront Condo with Two Balconies, Wet Bar, Beach Views & WiFi

Endless Tides - Marshfront Lands End Retreat. Pool Across Street. 500 Feet to Beach Access

Oceanfront Villa with kitchen, balcony, patio shared pool and trails

Stunning Oceanfront Villa - 3rd Floor Views and Renovated 2026

Exquisite oceanfront top-floor condo has the feel of paradise on earth

Serene Oceanfront Villa with WiFi, Pool, Hot Tub, & Fitness Center

Charming Waterfront Getaway with Seasonal Pool & Hot Tub, Tennis, Beach Access

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