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 289 to 336 of 337, page 7 of 8. Best rated first, then price.

Hilton Head Island waterfront stays

Oceanfront Condo with Shared Pool, Hot Tub, Beach Access & Playground

1609 Port Villa

Amazing oceanfront 2BR 2BA 1st floor condo with pool, hot tub, tennis, fitness area, & WD

Peaceful Oceanfront Villa with Pools, Hot Tub, Tennis, & Ocean View

2BR Beach Villa with Balcony Pool Tennis Access

Oceanfront condo with a washer, dryer, central AC, pool, hot tub & beach access

231 Breakers

Quiet Waterfront Condo with WiFi - Pools & Hot Tub On-Site

A Quiet Beach Getaway with Pools, Hot Tub, Tennis Courts, and Private Patio

First Floor, Oceanfront Condo with Free WiFi, Balcony, Shared Hot Tub, Pool, Sauna

Oceanfront Condo with Ocean View, Shared Pool Hot Tub, and Nearby Beach Access

Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access

A Relaxing Getaway with Shared Pools and Hot Tub in an Oceanfront Villa

Admiral's Row 130

Splendid condo, pool, full kitchen, & patio

Spacious updated oceanfront condo with shared pools, hot tub & beach access

Oceanfront condo with pools, hot tubs, WiFi, washer, dryer, & central AC

Luxury Villa Rooftop Pool near Beach Hilton Head

Beachfront escape with pools, hot tub, WiFi, washer dryer, & central AC

Beachfront getaway with WiFi, pools, hot tub, gym, washer dryer, & central AC

Ocean view condo at beachfront resort with pool, hot tub, pickleball & tennis

Coastal condo on the beach with panoramic views, beach access & a shared pool

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

Charming waterfront resort condo with pool, tennis, golf, & balcony

Cozy oceanfront villa, tennis courts, hot tub, shared pool and ocean view

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 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