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 241 to 288 of 357, page 6 of 8. Best rated first, then price.

from $152

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from $160

Pool Access! Oceanfront Hilton Head Island Condo

Oceanfront Entire condo 1 bed 1 bath sleeps 6

Hilton Head Island, SCrated 3.0

from $178

Pet Friendly Waterfront Villa w/ Dock, Hilton Head

Waterfront Condo 3 bed 3 bath sleeps 6 pets ok

Hilton Head Island, SCrated 3.0

Hilton Head Island waterfront stays

Harbourfront Condo in Harbour Town

Beach & Pool Access: Tranquil Hilton Head Getaway

Ocean Villas C346

Luxury Coastal Home, Pool & Hot Tub on Hilton Head

Exquisite Home w/ Private Pool & Dock Hilton Head

Home, 7 Miles to Savannah Historic District!

Pool, Spa & Dining: Beach Condo in Hilton Head!

Community Swimming Pool and Free Bikes - Charming Island Haven

Pool Access: Beachfront Hilton Head Resort Condo

10 Cassina Lane

Top Floor Condo at Beach & Tennis Resort Beachfront Pool & Golf access

Panoramic Views and Luxurious Features - Stunning Oceanfront Villa

Pool Access! Oceanfront Hilton Head Island Condo

Pet Friendly Waterfront Villa w/ Dock, Hilton Head

Beachfront villa near golf with pool, hot tub, & balcony - snowbird-friendly

Oceanfront resort condo with WiFi, balcony, pool, grills, & beach access

3rd Floor Condo with pools, tennis/pickleball courts, access to beach

Secluded & Peaceful - Vacation Getaway with WiFi, Pool, Hot Tub, & Private Beach

Perfectly Located Family Condo with Shared Pool, Central AC, Private Washer and dryer, Free WiFi

Spacious condo with pool, tennis courts, & golf on-site

Oceanview 4th Floor. 2BR Beach & Tennis Villa

Seaside 247

Waterfront villa with resort amenities, beach access, open layout, AC, & WD

Beachfront Villa W/ Pool & Tennis Hilton Head

Pet-Friendly Inverness Villa on Golf Course

2BR Queen's Grant Villa in Palmetto Dunes, Modern Furnishings, Prime Location, Community Pool!

Condo near beach with 2 pools, restaurants, gym, 6 tennis, 12 pickleball, W D

Waterfront condo with walkable locale, central AC, washer dryer, & shared pool

Hilton Head Beach & Tennis Resort, Oceanfront, Tennis, Restaurants, Pickleball!

Pet Friendly Villa with Patio, Pool, + Nearby Golf

Seaside 278

Open and Airy 3 Bed 2 Bath St Andrews Villa

Second-floor condo in beachfront complex with pools, tennis & gym

Oceanfront condo with WiFi, pool, hot tub & beach access

Spacious Patio and Community Pool - Elegant Coastal Hideaway

Spacious Villa with Balcony and Resort Amenities - Elegant Coastal Haven

Beachfront Getaway. Pool, Tennis + Ocean Air

Spacious Villa with Scenic Balcony and Resort Access - Stylish Coastal Haven

Coastal Escape w/ Pool & Ocean Peek!

Lagoon front, 3 story condo w balcony & washer dryer, snowbird-friendly

Waterfront Condo with Shared Pools, Hot Tubs, Private Balconies, and Ocean Views

Fully Equipped Kitchen and Resort Amenities Await - Spacious Villa Retreat

Beachfront condo w pool, tennis and pickleball, gym & balcony

Beach-view condo in oceanfront complex with outdoor pool, beach access, balcony

Waterfront condo with seasonal pools, hot tub, balcony, AC, & WD

Scenic Balcony and Resort Amenities - Charming Villa Retreat

Waterfront Condo with Ocean Views, Shared Pool, Hot Tub, and Covered Balcony

Seaside 358