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 145 to 192 of 337, page 4 of 8. Best rated first, then price.

Reel Paradise-Beautiful escape! Bikes & Chairs, Hilton Head Island, SC from $118

Reel Paradise-Beautiful escape! Bikes & Chairs

Oceanfront Condo 1 bed 1 bath sleeps 5
Hilton Head Island, SCrated 4.8
Admiral's Row 309: Beachfront Luxury Living, Hilton Head Island, SC from $121

Admiral's Row 309: Beachfront Luxury Living

Beachfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.8
Seaside 312, Hilton Head Island, SC from $124

Seaside 312

Oceanfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.8
Heated Pool and Stunning Ocean Views - Exquisite Beachfront Retreat, Hilton Head Island, SC from $129

Heated Pool and Stunning Ocean Views - Exquisite Beachfront Retreat

Beachfront Villa 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.8
Scenic Deck and Access to Community Pool - Tranquil Villa Haven, Hilton Head Island, SC from $132

Scenic Deck and Access to Community Pool - Tranquil Villa Haven

Oceanfront Villa 3 bed 2.5 bath sleeps 8
Hilton Head Island, SCrated 4.8
Oceanfront Access and Scenic Views - Charming Coastal Retreat, Hilton Head Island, SC from $151

Oceanfront Access and Scenic Views - Charming Coastal Retreat

Oceanfront Villa 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.8
Balcony Overlooking Tennis Courts and Resort Amenities - Charming Villa Escape, Hilton Head Island, SC from $155

Balcony Overlooking Tennis Courts and Resort Amenities - Charming Villa Escape

Beachfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.8
Oceanfront Pool and Spa Retreat - Amazing Ocean Views and Spacious Comfort, Hilton Head Island, SC from $200

Oceanfront Pool and Spa Retreat - Amazing Ocean Views and Spacious Comfort

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.8
Panoramic Ocean Views and Private Balcony - Charming Beachfront Haven, Hilton Head Island, SC from $202

Panoramic Ocean Views and Private Balcony - Charming Beachfront Haven

Beachfront Villa 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.8
Luxury Beachfront Villa w/ Pool, on Hilton Head, Hilton Head Island, SC from $207

Luxury Beachfront Villa w/ Pool, on Hilton Head

Beachfront Condo 2 bed 2 bath sleeps 8
Hilton Head Island, SCrated 4.8
Stunning Ocean Views and Community Pool - Exquisite Oceanfront Retreat, Hilton Head Island, SC from $223

Stunning Ocean Views and Community Pool - Exquisite Oceanfront Retreat

Oceanfront Villa 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.8
Ocean-View Balcony: Beachfront Hilton Head Condo, Hilton Head Island, SC from $224

Ocean-View Balcony: Beachfront Hilton Head Condo

Beachfront Entire condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.8
Compare before you book

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

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Pools + Sundeck: Beachfront Hilton Head Condo!, Hilton Head Island, SC from $250

Pools + Sundeck: Beachfront Hilton Head Condo!

Beachfront Entire condo 3 bed 2 bath sleeps 9
Hilton Head Island, SCrated 4.8
Charming Coastal Haven with Game Room and Screened Porch - Unique Escape, Hilton Head Island, SC from $259

Charming Coastal Haven with Game Room and Screened Porch - Unique Escape

Waterfront House 4 bed 3 bath sleeps 8 pets ok
Hilton Head Island, SCrated 4.8
Oceanfront Villa, Resort Amenities on Hilton Head, Hilton Head Island, SC from $270

Oceanfront Villa, Resort Amenities on Hilton Head

Oceanfront Condo 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 4.8
Oceanfront Pool and Beach Cruiser Bicycles - Stunning Coastal Haven, Hilton Head Island, SC from $273

Oceanfront Pool and Beach Cruiser Bicycles - Stunning Coastal Haven

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.8
Oceanfront Access and Community Pool - Beautiful Coastal Haven, Hilton Head Island, SC from $280

Oceanfront Access and Community Pool - Beautiful Coastal Haven

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.8
Oceanfront with Pool & Beach Access Hilton Head, Hilton Head Island, SC from $322

Oceanfront with Pool & Beach Access Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.8
Beachfront Condo w/ Pool Access in Hilton Head!, Hilton Head Island, SC from $327

Beachfront Condo w/ Pool Access in Hilton Head!

Beachfront Entire condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.8
Lagoon Front Oasis with Private Dock and Pool - Beautiful Tranquil Escape, Hilton Head Island, SC from $590

Lagoon Front Oasis with Private Dock and Pool - Beautiful Tranquil Escape

Bayfront House 4 bed 4 bath sleeps 12
Hilton Head Island, SCrated 4.8
Oceanfront Home with Private Pool and Hot Tub - Stunning Coastal Retreat, Hilton Head Island, SC from $1,379

Oceanfront Home with Private Pool and Hot Tub - Stunning Coastal Retreat

Oceanfront House 5 bed 5.5 bath sleeps 16
Hilton Head Island, SCrated 4.8
Seaside 337, Hilton Head Island, SC from $82

Seaside 337

Oceanfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.7
Seaside 315, Hilton Head Island, SC from $95

Seaside 315

Oceanfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.7
Seaside Villa 207 - Ocean Front with Balcony, Hilton Head Island, SC from $104

Seaside Villa 207 - Ocean Front with Balcony

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.7
Seaside 190, Hilton Head Island, SC from $105

Seaside 190

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.7
Rooftop Deck! Luxury Oceanfront Villa, Hilton Head, Hilton Head Island, SC from $240

Rooftop Deck! Luxury Oceanfront Villa, Hilton Head

Oceanfront Condo 3 bed 3 bath sleeps 10
Hilton Head Island, SCrated 4.7
Oceanfront Pools and Fitness Center - Exquisite Coastal Villa, Hilton Head Island, SC from $246

Oceanfront Pools and Fitness Center - Exquisite Coastal Villa

Oceanfront Villa 2 bed 2 bath sleeps 8
Hilton Head Island, SCrated 4.7
Panoramic Ocean Views and Sundeck - Charming Oceanfront Retreat, Hilton Head Island, SC from $255

Panoramic Ocean Views and Sundeck - Charming Oceanfront Retreat

Oceanfront Villa 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 4.7
Oceanfront Pool and Stunning Views - Gorgeous Villa Retreat, Hilton Head Island, SC from $277

Oceanfront Pool and Stunning Views - Gorgeous Villa Retreat

Oceanfront Villa 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 4.7
Oceanfront Penthouse Villa w/ Balcony, Hilton Head, Hilton Head Island, SC from $338

Oceanfront Penthouse Villa w/ Balcony, Hilton Head

Oceanfront Condo 3 bed 3 bath sleeps 10
Hilton Head Island, SCrated 4.7
Oceanfront Escape with Pools and Spa - Stunning Coastal Haven, Hilton Head Island, SC from $396

Oceanfront Escape with Pools and Spa - Stunning Coastal Haven

Oceanfront Villa 3 bed 3 bath sleeps 10
Hilton Head Island, SCrated 4.7
Oceanfront Pool and Stunning Views - Elegant Coastal Sanctuary, Hilton Head Island, SC from $452

Oceanfront Pool and Stunning Views - Elegant Coastal Sanctuary

Oceanfront Villa 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 4.7
Expansive Living Areas and Dual Entrances - Stunning Coastal Haven, Hilton Head Island, SC from $622

Expansive Living Areas and Dual Entrances - Stunning Coastal Haven

Oceanfront Villa 5 bed 5.5 bath sleeps 14
Hilton Head Island, SCrated 4.7
Oceanfront Oasis with Private Pool and Spa - Elegant Getaway, Hilton Head Island, SC from $1,441

Oceanfront Oasis with Private Pool and Spa - Elegant Getaway

Oceanfront House 8 bed 8 bath sleeps 20 pets ok
Hilton Head Island, SCrated 4.7
Shipmaster Villa 801 - Perfect Beach and Golf, Hilton Head Island, SC from $101

Shipmaster Villa 801 - Perfect Beach and Golf

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.6
Luxury Oceanfront Villa, w/ Pool on Hilton Head, Hilton Head Island, SC from $101

Luxury Oceanfront Villa, w/ Pool on Hilton Head

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.6
Gone Coastal! 2 from oceanfront! Central air!, Hilton Head Island, SC from $112

Gone Coastal! 2 from oceanfront! Central air!

Oceanfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.6
Closest 2 BR to the Beach! Hilton Head Condo, Hilton Head Island, SC from $173

Closest 2 BR to the Beach! Hilton Head Condo

Beachfront Entire condo 2 bed 2 bath sleeps 4
Hilton Head Island, SCrated 4.6
67 Night Heron @ Sea Pines - Waterfront Villa, Hilton Head Island, SC from $179

67 Night Heron @ Sea Pines - Waterfront Villa

Waterfront House 3 bed 2 bath sleeps 8
Hilton Head Island, SCrated 4.6
Oceanfront Hilton Head Island Condo w/ Pool!, Hilton Head Island, SC from $189

Oceanfront Hilton Head Island Condo w/ Pool!

Oceanfront Entire condo 1 bed 1 bath sleeps 3
Hilton Head Island, SCrated 4.6
233 Breakers, Hilton Head Island, SC from $191

233 Breakers

Oceanfront Villa 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.6
Oceanfront Pools and Cozy Decor - Charming Villa Escape, Hilton Head Island, SC from $213

Oceanfront Pools and Cozy Decor - Charming Villa Escape

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.6
Oceanfront Pool and Free Bikes - Inviting Coastal Haven, Hilton Head Island, SC from $232

Oceanfront Pool and Free Bikes - Inviting Coastal Haven

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.6
Oceanfront Pools and Breathtaking Views - Luxurious Beachfront Haven, Hilton Head Island, SC from $321

Oceanfront Pools and Breathtaking Views - Luxurious Beachfront Haven

Beachfront Villa 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 4.6
Ocean Views and Community Pool - Stunning Oceanfront Retreat, Hilton Head Island, SC from $330

Ocean Views and Community Pool - Stunning Oceanfront Retreat

Oceanfront Villa 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 4.6
Luxury Beachfront Villa w/ Pool on Hilton Head, Hilton Head Island, SC from $382

Luxury Beachfront Villa w/ Pool on Hilton Head

Beachfront Condo 3 bed 3 bath sleeps 10
Hilton Head Island, SCrated 4.6
Luxury Home w/Pool & Spa Near Beach on Hilton Head, Hilton Head Island, SC from $392

Luxury Home w/Pool & Spa Near Beach on Hilton Head

Oceanfront House 6 bed 5 bath sleeps 14
Hilton Head Island, SCrated 4.6
Charming Villa with Cozy Living and Marina Access - Inviting Retreat, Hilton Head Island, SC from $437

Charming Villa with Cozy Living and Marina Access - Inviting Retreat

Waterfront Condo 3 bed 3 bath sleeps 8 pets ok
Hilton Head Island, SCrated 4.6
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.

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