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 49 to 96 of 357, page 2 of 8. Best rated first, then price.

7447 Anchorage, Hilton Head Island, SC from $180

7447 Anchorage

Oceanfront Villa 2 bed 2 bath sleeps 6 pets ok
Hilton Head Island, SCrated 5.0
Pool Time & Island Vibes! Hilton Head Getaway, Hilton Head Island, SC from $185

Pool Time & Island Vibes! Hilton Head Getaway

Waterfront Entire condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 5.0
2 Mi to Beach: Condo w/ Pool Access in Hilton Head, Hilton Head Island, SC from $200

2 Mi to Beach: Condo w/ Pool Access in Hilton Head

Oceanfront Entire condo 2 bed 2 bath sleeps 5
Hilton Head Island, SCrated 5.0
Breakers 328 Oceanfront Hilton Head Condo. Stunning Beach View & Pool, Hilton Head Island, SC from $202

Breakers 328 Oceanfront Hilton Head Condo. Stunning Beach View & Pool

Oceanfront Apartment 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 5.0
5 Hickory Cove, Hilton Head Island, SC from $205

5 Hickory Cove

Bayfront Villa 3 bed 4 bath sleeps 10 pets ok
Hilton Head Island, SCrated 5.0
Heron's Rest at Port Villas by AvantStay. Waterfront Cove + Dock + Deck. Walk to Beach + Sea Pines, Hilton Head Island, SC from $208

Heron's Rest at Port Villas by AvantStay. Waterfront Cove + Dock + Deck. Walk to Beach + Sea Pines

Waterfront House 3 bed 3 bath sleeps 8 pets ok
Hilton Head Island, SCrated 5.0
Beachside Luxury Villa w/ Pool on Hilton Head, Hilton Head Island, SC from $214

Beachside Luxury Villa w/ Pool on Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Stunning Ocean Views and Cozy Retreat - Exquisite Oceanfront Escape, Hilton Head Island, SC from $217

Stunning Ocean Views and Cozy Retreat - Exquisite Oceanfront Escape

Oceanfront Villa 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 5.0
4501 Island Club, Hilton Head Island, SC from $218

4501 Island Club

Oceanfront Villa 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 5.0
Oceanfront Pools and Stunning Views - Exquisite Coastal Retreat, Hilton Head Island, SC from $220

Oceanfront Pools and Stunning Views - Exquisite Coastal Retreat

Oceanfront Villa 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 5.0
4202 Windsor Court North, Hilton Head Island, SC from $228

4202 Windsor Court North

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Coastal Soul-Gorgeous Direct OceanFront!, Hilton Head Island, SC from $230

Coastal Soul-Gorgeous Direct OceanFront!

Oceanfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Compare before you book

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

Search Vrbo → Booking.com → Affiliate links.
Inviting Outdoor Oasis with Pool and Billiard Room - Charming Retreat, Hilton Head Island, SC from $232

Inviting Outdoor Oasis with Pool and Billiard Room - Charming Retreat

Waterfront House 3 bed 3 bath sleeps 8 pets ok
Hilton Head Island, SCrated 5.0
Expansive Balcony and Community Pool - Stunning Oceanfront Villa, Hilton Head Island, SC from $236

Expansive Balcony and Community Pool - Stunning Oceanfront Villa

Oceanfront Villa 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 5.0
Sea Pines 3BR. Beach & Harbour Town & Pool Access, Hilton Head Island, SC from $243

Sea Pines 3BR. Beach & Harbour Town & Pool Access

Oceanfront House 3 bed 2 bath sleeps 8
Hilton Head Island, SCrated 5.0
2 Mi to Beach! Hilton Head Golf Escape w/ Balcony, Hilton Head Island, SC from $243

2 Mi to Beach! Hilton Head Golf Escape w/ Balcony

Waterfront Entire condo 2 bed 2 bath sleeps 4 pets ok
Hilton Head Island, SCrated 5.0
Beachfront Access and Community Pool - Stunning Coastal Retreat, Hilton Head Island, SC from $258

Beachfront Access and Community Pool - Stunning Coastal Retreat

Beachfront Villa 2 bed 2 bath sleeps 8
Hilton Head Island, SCrated 5.0
Oceanfront Villa w/ Pool Beach Access Hilton Head, Hilton Head Island, SC from $298

Oceanfront Villa w/ Pool Beach Access Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Oceanfront Villa w/Wrap Around Balcony Hilton Head, Hilton Head Island, SC from $306

Oceanfront Villa w/Wrap Around Balcony Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 5.0
Stylish Dog-Friendly Oasis Near Beach & Lagoon, Hilton Head Island, SC from $313

Stylish Dog-Friendly Oasis Near Beach & Lagoon

Oceanfront House 4 bed 2 bath sleeps 10 pets ok
Hilton Head Island, SCrated 5.0
Steps to Beach! Oceanfront Hilton Head Villa, Pool, Hilton Head Island, SC from $313

Steps to Beach! Oceanfront Hilton Head Villa, Pool

Oceanfront Condo 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 5.0
Ocean Views and Zero-Entry Pool - Charming Oceanfront Retreat, Hilton Head Island, SC from $314

Ocean Views and Zero-Entry Pool - Charming Oceanfront Retreat

Oceanfront Condo 3 bed 3 bath sleeps 10
Hilton Head Island, SCrated 5.0
Private Pool Retreat on One Level. 2 Living Areas. Pet Friendly. Near Palmetto Dunes Beaches, Hilton Head Island, SC from $327

Private Pool Retreat on One Level. 2 Living Areas. Pet Friendly. Near Palmetto Dunes Beaches

Oceanfront House 4 bed 3 bath sleeps 9 pets ok
Hilton Head Island, SCrated 5.0
Oceanfront Access and Spacious Deck - Elegant Coastal Retreat, Hilton Head Island, SC from $331

Oceanfront Access and Spacious Deck - Elegant Coastal Retreat

Oceanfront Villa 4 bed 4 bath sleeps 8
Hilton Head Island, SCrated 5.0
Rooftop Sun Deck! Luxury Hilton Head Villa w/ Pool, Hilton Head Island, SC from $342

Rooftop Sun Deck! Luxury Hilton Head Villa w/ Pool

Oceanfront Condo 3 bed 3 bath sleeps 9
Hilton Head Island, SCrated 5.0
Luxurious Pool and Spa with Lagoon Access - Gorgeous Family Getaway, Hilton Head Island, SC from $349

Luxurious Pool and Spa with Lagoon Access - Gorgeous Family Getaway

Canal front House 4 bed 4 bath sleeps 12
Hilton Head Island, SCrated 5.0
137 Shorewood, Hilton Head Island, SC from $353

137 Shorewood

Beachfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Waterfront, Ocean View Condo with Tennis, Pools, Hot Tub, and Beaches, Hilton Head Island, SC from $357

Waterfront, Ocean View Condo with Tennis, Pools, Hot Tub, and Beaches

Waterfront Condo 3 bed 3 bath sleeps 7
Hilton Head Island, SCrated 5.0
Charming Lakefront Retreat in Palmetto Dunes!, Hilton Head Island, SC from $361

Charming Lakefront Retreat in Palmetto Dunes!

Lakefront Entire home 3 bed 2 bath sleeps 8
Hilton Head Island, SCrated 5.0
Bluffton Getaway w/ Fenced Yard: 7 Mi to Beach!, Bluffton, SC from $365

Bluffton Getaway w/ Fenced Yard: 7 Mi to Beach!

Oceanfront Entire home 3 bed 2 bath sleeps 6 pets ok
Bluffton, SCrated 5.0
Stunning Villa with Direct Beach Access - Elegant Oceanfront Retreat, Hilton Head Island, SC from $370

Stunning Villa with Direct Beach Access - Elegant Oceanfront Retreat

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
1922 South Beach Club, Hilton Head Island, SC from $372

1922 South Beach Club

Oceanfront Villa 3 bed 2.5 bath sleeps 6 pets ok
Hilton Head Island, SCrated 5.0
Beachside Luxury Villa, Pool & Spa, on Hilton Head, Hilton Head Island, SC from $409

Beachside Luxury Villa, Pool & Spa, on Hilton Head

Oceanfront Condo 3 bed 3 bath sleeps 10
Hilton Head Island, SCrated 5.0
Oceanfront Villa w/Pool Beach Access Hilton Head, Hilton Head Island, SC from $426

Oceanfront Villa w/Pool Beach Access Hilton Head

Oceanfront Condo 3 bed 3 bath sleeps 10
Hilton Head Island, SCrated 5.0
Luxury Riverfront Retreat in the Eastern Wharf. Heated Pool Access, Savannah, GA from $489

Luxury Riverfront Retreat in the Eastern Wharf. Heated Pool Access

Waterfront Townhouse 3 bed 3 bath sleeps 6
Savannah, GArated 5.0
Extravagant Hilton Head Luxury Home Private Pool, Hilton Head Island, SC from $530

Extravagant Hilton Head Luxury Home Private Pool

Oceanfront House 3 bed 4 bath sleeps 10
Hilton Head Island, SCrated 5.0
Private Marshfront Oasis w/ Pool & Sunset Views, Hilton Head Island, SC from $557

Private Marshfront Oasis w/ Pool & Sunset Views

Soundfront House 4 bed 4 bath sleeps 8
Hilton Head Island, SCrated 5.0
Luxury Oceanfront Villa w/ Pool & Spa Hilton Head, Hilton Head Island, SC from $569

Luxury Oceanfront Villa w/ Pool & Spa Hilton Head

Oceanfront Condo 4 bed 4 bath sleeps 12
Hilton Head Island, SCrated 5.0
Private Patio and Community Pool - Exquisite Oceanfront Retreat, Hilton Head Island, SC from $575

Private Patio and Community Pool - Exquisite Oceanfront Retreat

Oceanfront Condo 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 5.0
Private Pool and Spa with Outdoor Kitchen - Luxurious Family Retreat, Hilton Head Island, SC from $718

Private Pool and Spa with Outdoor Kitchen - Luxurious Family Retreat

Oceanfront House 5 bed 4.5 bath sleeps 14
Hilton Head Island, SCrated 5.0
135 Mooring Buoy, Hilton Head Island, SC from $754

135 Mooring Buoy

Bayfront House 5 bed 6 bath sleeps 14 pets ok
Hilton Head Island, SCrated 5.0
Massive Luxury Beach Home Private Pool Hilton Head, Hilton Head Island, SC from $777

Massive Luxury Beach Home Private Pool Hilton Head

Beachfront House 6 bed 5 bath sleeps 18
Hilton Head Island, SCrated 5.0
Expansive Backyard Oasis and Upper Sun Terrace - Exquisite Coastal Retreat, Hilton Head Island, SC from $825

Expansive Backyard Oasis and Upper Sun Terrace - Exquisite Coastal Retreat

Beachfront House 6 bed 1 bath sleeps 14
Hilton Head Island, SCrated 5.0
Spacious Home with Pool and Spa - Elegant Coastal Retreat, Hilton Head Island, SC from $973

Spacious Home with Pool and Spa - Elegant Coastal Retreat

Oceanfront House 6 bed 6 bath sleeps 16
Hilton Head Island, SCrated 5.0
Oceanfront 5BR, Private Pool, Sleeps 13, Upper Balcony Views, in Forest Beach, Hilton Head Island, SC from $1,055

Oceanfront 5BR, Private Pool, Sleeps 13, Upper Balcony Views, in Forest Beach

Oceanfront House 5 bed 5 bath sleeps 13
Hilton Head Island, SCrated 5.0
Exclusive Pool and Five Unique Apartments - Stunning Beachside Villa, Tybee Island, GA from $1,214

Exclusive Pool and Five Unique Apartments - Stunning Beachside Villa

Beachfront Villa 9 bed 8 bath sleeps 28
Tybee Island, GArated 5.0
Luxury Pool and Spa Oasis - Stunning Oceanfront Escape, Hilton Head Island, SC from $1,338

Luxury Pool and Spa Oasis - Stunning Oceanfront Escape

Oceanfront House 6 bed 5 bath sleeps 14
Hilton Head Island, SCrated 5.0
Private Pool, Outdoor Hot Tub, Gourmet Kitchen - Stunning Retreat, Hilton Head Island, SC from $1,380

Private Pool, Outdoor Hot Tub, Gourmet Kitchen - Stunning Retreat

Beachfront House 6 bed 6 bath sleeps 12
Hilton Head Island, SCrated 5.0
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 →

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