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 97 to 144 of 357, page 3 of 8. Best rated first, then price.

Heated Pool and Spa with Private Beach Access - Stunning Oceanfront Escape, Hilton Head Island, SC from $1,415

Heated Pool and Spa with Private Beach Access - Stunning Oceanfront Escape

Oceanfront House 8 bed 7 bath sleeps 19
Hilton Head Island, SCrated 5.0
Unique Dock House and Scenic Water Views - Stunning Waterfront Estate, Okatie, SC from $1,932

Unique Dock House and Scenic Water Views - Stunning Waterfront Estate

Waterfront Apartment 5 bed 5.5 bath sleeps 28
Okatie, SCrated 5.0
Luxurious Oceanfront Haven with Huge Pool and Entertainment Area - Exquisite Retreat, Hilton Head Island, SC from $2,901

Luxurious Oceanfront Haven with Huge Pool and Entertainment Area - Exquisite Retreat

Oceanfront House 6 bed 7 bath sleeps 24
Hilton Head Island, SCrated 5.0
Oceanfront Paradise with Pool and Spa - Stunning Coastal Retreat, Hilton Head Island, SC from $2,922

Oceanfront Paradise with Pool and Spa - Stunning Coastal Retreat

Beachfront House 7 bed 8 bath sleeps 26
Hilton Head Island, SCrated 5.0
Tennis Villa F14 - Beach and Pool, Hilton Head Island, SC from $77

Tennis Villa F14 - Beach and Pool

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Seaside 279, Hilton Head Island, SC from $98

Seaside 279

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.9
Beachfront Villa W/ Pool & Tennis Hilton Head, Hilton Head Island, SC from $100

Beachfront Villa W/ Pool & Tennis Hilton Head

Beachfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.9
Oceanfront Villa w/Pool & Beach Access Hilton Head, Hilton Head Island, SC from $101

Oceanfront Villa w/Pool & Beach Access Hilton Head

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.9
Oceanfront Pool and Sunny Sun Deck - Unique Coastal Villa, Hilton Head Island, SC from $106

Oceanfront Pool and Sunny Sun Deck - Unique Coastal Villa

Oceanfront Villa 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.9
Seaside 102, Hilton Head Island, SC from $106

Seaside 102

Oceanfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.9
Coastal Retreat: 4th Floor Balcony & Sunrises, Hilton Head Island, SC from $113

Coastal Retreat: 4th Floor Balcony & Sunrises

Beachfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Renovated Luxury Villa w/ Patio & Pool Hilton Head, Hilton Head Island, SC from $113

Renovated Luxury Villa w/ Patio & Pool Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 4.9
Compare before you book

See Hilton Head Island on Vrbo, with dates and live prices.

Search Vrbo → Booking.com → Affiliate links.
Community Pool and Scenic Balcony - Delightful Coastal Escape, Hilton Head Island, SC from $116

Community Pool and Scenic Balcony - Delightful Coastal Escape

Beachfront Villa 2 bed 2 bath sleeps 6 pets ok
Hilton Head Island, SCrated 4.9
Seaside 386, Hilton Head Island, SC from $118

Seaside 386

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.9
SerenityByTheSea-Couples Retreat-King,Bikes,Chairs, Hilton Head Island, SC from $123

SerenityByTheSea-Couples Retreat-King,Bikes,Chairs

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.9
Beautiful Couples Retreat Oceanview w/new bikes&Ch, Hilton Head Island, SC from $132

Beautiful Couples Retreat Oceanview w/new bikes&Ch

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.9
7813 Centre Court, Hilton Head Island, SC from $138

7813 Centre Court

Beachfront Villa 2 bed 2 bath sleeps 8
Hilton Head Island, SCrated 4.9
Charming Oceanfront Escape with Heated Pools and Spa - Inviting Haven, Hilton Head Island, SC from $145

Charming Oceanfront Escape with Heated Pools and Spa - Inviting Haven

Oceanfront Condo 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 4.9
Community Pool and Coastal Decor - Tranquil Island Escape, Hilton Head Island, SC from $147

Community Pool and Coastal Decor - Tranquil Island Escape

Oceanfront Villa 2 bed 2 bath sleeps 6 pets ok
Hilton Head Island, SCrated 4.9
Scenic Patio and Resort Amenities - Exquisite Coastal Retreat, Hilton Head Island, SC from $148

Scenic Patio and Resort Amenities - Exquisite Coastal Retreat

Oceanfront Condo 3 bed 2 bath sleeps 6 pets ok
Hilton Head Island, SCrated 4.9
Breakers 220 Hilton Head. Oceanfront. Heated Pool. Elevator. Renovated, Hilton Head Island, SC from $152

Breakers 220 Hilton Head. Oceanfront. Heated Pool. Elevator. Renovated

Oceanfront Apartment 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.9
High Speed Wi-Fi and Two-Person Jacuzzi Tub - Charming Lake Home, Wilmington Island, GA from $153

High Speed Wi-Fi and Two-Person Jacuzzi Tub - Charming Lake Home

Waterfront Vacation Rental 4 bed 2 bath sleeps 10 pets ok
Wilmington Island, GArated 4.9
Beachfront Access and Free Bicycles - Charming Coastal Haven, Hilton Head Island, SC from $153

Beachfront Access and Free Bicycles - Charming Coastal Haven

Beachfront Villa 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.9
Private Balcony and Resort Amenities - Charming Villa Retreat, Hilton Head Island, SC from $156

Private Balcony and Resort Amenities - Charming Villa Retreat

Beachfront Condo 2 bed 2 bath sleeps 8
Hilton Head Island, SCrated 4.9
Spacious Pool Area and Ocean Access - Charming Coastal Haven, Hilton Head Island, SC from $156

Spacious Pool Area and Ocean Access - Charming Coastal Haven

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Waterfront Villa w/dock near Dining Hilton Head, Hilton Head Island, SC from $160

Waterfront Villa w/dock near Dining Hilton Head

Waterfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Seaside 357, Hilton Head Island, SC from $161

Seaside 357

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.9
Luxurious Beachfront Access and Stunning Ocean Views - Colorful Oasis, Tybee Island, GA from $165

Luxurious Beachfront Access and Stunning Ocean Views - Colorful Oasis

Beachfront Condo 1 bed 1 bath sleeps 4
Tybee Island, GArated 4.9
Oceanfront Luxury Villa w/ Pool on Hilton Head, Hilton Head Island, SC from $165

Oceanfront Luxury Villa w/ Pool on Hilton Head

Oceanfront Condo 1 bed 2 bath sleeps 4
Hilton Head Island, SCrated 4.9
Luxury Waterfront Villa w/ Dock on Hilton Head, Hilton Head Island, SC from $172

Luxury Waterfront Villa w/ Dock on Hilton Head

Waterfront Condo 2 bed 2 bath sleeps 4 pets ok
Hilton Head Island, SCrated 4.9
Beachfront Villa With Ocean Views Hilton Head, Hilton Head Island, SC from $180

Beachfront Villa With Ocean Views Hilton Head

Beachfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Serene Escape with Community Pool and Bicycles - Tranquil Oasis, Hilton Head Island, SC from $184

Serene Escape with Community Pool and Bicycles - Tranquil Oasis

Oceanfront Villa 2 bed 2 bath sleeps 6 pets ok
Hilton Head Island, SCrated 4.9
Oceanfront Villa, Pool Prime Location! Hilton Head, Hilton Head Island, SC from $185

Oceanfront Villa, Pool Prime Location! Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 4.9
1608 Port Villa, Hilton Head Island, SC from $194

1608 Port Villa

Canal front House 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 4.9
Oceanfront Pool and Beach Cruisers - Exquisite Coastal Escape, Hilton Head Island, SC from $206

Oceanfront Pool and Beach Cruisers - Exquisite Coastal Escape

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Spacious Living and Two Oceanfront Pools - Gorgeous Ocean View Villa, Hilton Head Island, SC from $208

Spacious Living and Two Oceanfront Pools - Gorgeous Ocean View Villa

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Private Dock and Bubbling Hot Tub - Charming Idyllic Retreat, Talahi Island, GA from $213

Private Dock and Bubbling Hot Tub - Charming Idyllic Retreat

Canal front House 4 bed 4 bath sleeps 10 pets ok
Talahi Island, GArated 4.9
Oceanfront Villa w/ Rooftop Pool on Hilton Head, Hilton Head Island, SC from $215

Oceanfront Villa w/ Rooftop Pool on Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Oceanfront Condo! Breakers 210 w/ Sunrise Views, Hilton Head Island, SC from $219

Oceanfront Condo! Breakers 210 w/ Sunrise Views

Oceanfront Entire condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.9
Oceanfront Pool and Luxurious Amenities - Serene Coastal Haven, Hilton Head Island, SC from $258

Oceanfront Pool and Luxurious Amenities - Serene Coastal Haven

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Oceanfront Pool and Scenic Views - Stunning Coastal Haven, Hilton Head Island, SC from $318

Oceanfront Pool and Scenic Views - Stunning Coastal Haven

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Oceanfront Escape with Pools and Hot Tub - Stunning Coastal Haven, Hilton Head Island, SC from $339

Oceanfront Escape with Pools and Hot Tub - Stunning Coastal Haven

Oceanfront Vacation Rental 2 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.9
Oceanfront Villa. Heated Pool. South Forest Beach, Hilton Head Island, SC from $378

Oceanfront Villa. Heated Pool. South Forest Beach

Oceanfront Entire condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.9
Breathtaking Ocean Views and Resort Style Pools - Amazing Beachfront Oasis, Hilton Head Island, SC from $397

Breathtaking Ocean Views and Resort Style Pools - Amazing Beachfront Oasis

Beachfront Condo 2 bed 2 bath sleeps 5
Hilton Head Island, SCrated 4.9
Exclusive Heated Pool and Spacious Living - Luxurious Coastal Haven, Tybee Island, GA from $423

Exclusive Heated Pool and Spacious Living - Luxurious Coastal Haven

Oceanfront House 4 bed 2 bath sleeps 12
Tybee Island, GArated 4.9
Oceanfront Balcony and Spacious Living Areas - Stunning Coastal Haven, Hilton Head Island, SC from $448

Oceanfront Balcony and Spacious Living Areas - Stunning Coastal Haven

Oceanfront Villa 3 bed 3.5 bath sleeps 8
Hilton Head Island, SCrated 4.9
Stylish Sea Pines Home Hot Tub, Hilton Head, Hilton Head Island, SC from $477

Stylish Sea Pines Home Hot Tub, Hilton Head

Waterfront House 4 bed 3 bath sleeps 8
Hilton Head Island, SCrated 4.9
Private Pool and Games Room Retreat - Gorgeous Marshside Haven, Hilton Head Island, SC from $505

Private Pool and Games Room Retreat - Gorgeous Marshside Haven

Soundfront House 4 bed 3 bath sleeps 13
Hilton Head Island, SCrated 4.9
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 →
Every shore

Ten shores, each with its own stays list and curated picks.

All beach stays →

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.

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