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 1 to 48 of 357, page 1 of 8. Best rated first, then price.

Renovated condo on the beach with pool, balcony, central AC, W D, & fitness room, Hilton Head Island, SC from $77

Renovated condo on the beach with pool, balcony, central AC, W D, & fitness room

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Modern Ocean Villa A204. Renovated & Bright, Hilton Head Island, SC from $93

Modern Ocean Villa A204. Renovated & Bright

Beachfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 5.0
Waterfront condo with private balcony, W D and near beach and marina, Hilton Head Island, SC from $95

Waterfront condo with private balcony, W D and near beach and marina

Waterfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Nautical touches abound at this renovated waterfront condo with pool & tennis, Hilton Head Island, SC from $98

Nautical touches abound at this renovated waterfront condo with pool & tennis

Waterfront Condo 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 5.0
Beachfront Villa W/ Pool & Tennis Hilton Head, Hilton Head Island, SC from $101

Beachfront Villa W/ Pool & Tennis Hilton Head

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Beachside Bliss, Newly Renovated, Pet Friendly, Hilton Head Island, SC from $102

Beachside Bliss, Newly Renovated, Pet Friendly

Waterfront Condo 2 bed 2 bath sleeps 6 pets ok
Hilton Head Island, SCrated 5.0
736 Queens Grant @ Palmetto Dunes. Updated Condo. Prime Location, Hilton Head Island, SC from $106

736 Queens Grant @ Palmetto Dunes. Updated Condo. Prime Location

Oceanfront Condo 2 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Admiral's Row. 3rd Floor Gem. Beachfront Balcony, Hilton Head Island, SC from $106

Admiral's Row. 3rd Floor Gem. Beachfront Balcony

Beachfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Cozy Retreat with Oceanfront Pool and Tennis Courts - Charming Escape, Hilton Head Island, SC from $111

Cozy Retreat with Oceanfront Pool and Tennis Courts - Charming Escape

Oceanfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Charming Villa with Outdoor Courtyard - Cozy Coastal Escape, Hilton Head Island, SC from $111

Charming Villa with Outdoor Courtyard - Cozy Coastal Escape

Oceanfront Condo 2 bed 1 bath sleeps 6 pets ok
Hilton Head Island, SCrated 5.0
Balcony, Pool Access and Tennis Courts - Charming Coastal Retreat, Hilton Head Island, SC from $116

Balcony, Pool Access and Tennis Courts - Charming Coastal Retreat

Beachfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 5.0
Oceanfront Pool and Hot Tub - Elegant Coastal Escape, Hilton Head Island, SC from $118

Oceanfront Pool and Hot Tub - Elegant Coastal Escape

Oceanfront Villa 1 bed 1.5 bath sleeps 4
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.
Queens Grant 655, Hilton Head Island, SC from $118

Queens Grant 655

Oceanfront Condo 2 bed 1 bath sleeps 5
Hilton Head Island, SCrated 5.0
Spacious Villa with Balcony and Pool Access - Charming Coastal Getaway, Hilton Head Island, SC from $119

Spacious Villa with Balcony and Pool Access - Charming Coastal Getaway

Beachfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 5.0
Renovated Coastal Villa, Pet Friendly! Hilton Head, Hilton Head Island, SC from $120

Renovated Coastal Villa, Pet Friendly! Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 4 pets ok
Hilton Head Island, SCrated 5.0
Steps to Beach! 2BR Oceanfront Pool, Private Balcony & Coastal Charm, Hilton Head Island, SC from $121

Steps to Beach! 2BR Oceanfront Pool, Private Balcony & Coastal Charm

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Balcony, Pool, and Tennis Court Access - Spacious Coastal Haven, Hilton Head Island, SC from $121

Balcony, Pool, and Tennis Court Access - Spacious Coastal Haven

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Ocean Access and Elegant Amenities - Charming Coastal Haven, Hilton Head Island, SC from $121

Ocean Access and Elegant Amenities - Charming Coastal Haven

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Elegant Villa w/ Pool, Golf & Beach, Hilton Head, Hilton Head Island, SC from $122

Elegant Villa w/ Pool, Golf & Beach, Hilton Head

Oceanfront Condo 2 bed 1 bath sleeps 5
Hilton Head Island, SCrated 5.0
Fully Equipped Kitchen and Access to Pool and Beach - Spacious Coastal Haven, Hilton Head Island, SC from $122

Fully Equipped Kitchen and Access to Pool and Beach - Spacious Coastal Haven

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Spacious Villa with Balcony and Resort Amenities - Charming Coastal Haven, Hilton Head Island, SC from $122

Spacious Villa with Balcony and Resort Amenities - Charming Coastal Haven

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Scenic Balcony and Access to Pools - Charming Coastal Getaway, Hilton Head Island, SC from $123

Scenic Balcony and Access to Pools - Charming Coastal Getaway

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Balcony and Access to Stunning Beach Activities - Beautiful Coastal Haven, Hilton Head Island, SC from $124

Balcony and Access to Stunning Beach Activities - Beautiful Coastal Haven

Beachfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 5.0
Balcony, Pool Access and Tennis Courts - Charming Coastal Oasis, Hilton Head Island, SC from $124

Balcony, Pool Access and Tennis Courts - Charming Coastal Oasis

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Scenic Balcony and Fully Equipped Kitchenette - Charming Coastal Retreat, Hilton Head Island, SC from $124

Scenic Balcony and Fully Equipped Kitchenette - Charming Coastal Retreat

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Private Balcony and Resort Amenities - Beautiful Coastal Retreat, Hilton Head Island, SC from $124

Private Balcony and Resort Amenities - Beautiful Coastal Retreat

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Balcony, Pool Access and Tennis Courts - Spacious Coastal Haven, Hilton Head Island, SC from $125

Balcony, Pool Access and Tennis Courts - Spacious Coastal Haven

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Charming Oasis with Outdoor Patio and Resort Amenities - Cozy Retreat, Hilton Head Island, SC from $125

Charming Oasis with Outdoor Patio and Resort Amenities - Cozy Retreat

Oceanfront Condo 3 bed 3 bath sleeps 12 pets ok
Hilton Head Island, SCrated 5.0
Spacious Villa with Balcony and Resort Amenities - Charming Coastal Escape, Hilton Head Island, SC from $125

Spacious Villa with Balcony and Resort Amenities - Charming Coastal Escape

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Balcony and Access to Resort Amenities - Spacious Coastal Retreat, Hilton Head Island, SC from $126

Balcony and Access to Resort Amenities - Spacious Coastal Retreat

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Fairytale Escape w/ Pool, Tennis Golf Hilton Head, Hilton Head Island, SC from $131

Fairytale Escape w/ Pool, Tennis Golf Hilton Head

Oceanfront Condo 1 bed 1 bath sleeps 4 pets ok
Hilton Head Island, SCrated 5.0
Spacious Villa with Balcony and Resort Amenities - Charming Beach Haven, Hilton Head Island, SC from $136

Spacious Villa with Balcony and Resort Amenities - Charming Beach Haven

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Panoramic Views and Luxurious Amenities - Gorgeous Oceanfront Escape, Hilton Head Island, SC from $137

Panoramic Views and Luxurious Amenities - Gorgeous Oceanfront Escape

Oceanfront Condo 1 bed 1 bath sleeps 5
Hilton Head Island, SCrated 5.0
Oceanfront Retreat 318 Breakers, Hilton Head Island, SC from $138

Oceanfront Retreat 318 Breakers

Oceanfront Villa 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Furnished Balcony and Access to Tennis Courts and Pool - Charming Coastal Retreat, Hilton Head Island, SC from $141

Furnished Balcony and Access to Tennis Courts and Pool - Charming Coastal Retreat

Beachfront Condo 1 bed 1 bath sleeps 2
Hilton Head Island, SCrated 5.0
Beachfront condo with large furnished balcony, pool & beautiful views, Hilton Head Island, SC from $145

Beachfront condo with large furnished balcony, pool & beautiful views

Beachfront Condo 2 bed 2 bath sleeps 8
Hilton Head Island, SCrated 5.0
Coastal Luxury! Pool, Golf, Beach Hilton Head, Hilton Head Island, SC from $148

Coastal Luxury! Pool, Golf, Beach Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 7 pets ok
Hilton Head Island, SCrated 5.0
Palmetto Dunes Chic 2BR Villa Pickleball Golf Pool, Hilton Head Island, SC from $150

Palmetto Dunes Chic 2BR Villa Pickleball Golf Pool

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Coastal Chic Villa Near Beach and Shops, Hilton Head Island, SC from $156

Coastal Chic Villa Near Beach and Shops

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Forest Beach Condo. Community Pool. Oceanfront Private Beach Access. Elegant Furnishings, Hilton Head Island, SC from $163

Forest Beach Condo. Community Pool. Oceanfront Private Beach Access. Elegant Furnishings

Oceanfront Condo 2 bed 2 bath sleeps 4
Hilton Head Island, SCrated 5.0
Private Dock and Hot Tub with Lake View - Charming Tranquil Retreat, Talahi Island, GA from $165

Private Dock and Hot Tub with Lake View - Charming Tranquil Retreat

Canal front House 3 bed 3 bath sleeps 8 pets ok
Talahi Island, GArated 5.0
Luxury Villa Golf Beach & Pool Access Hilton Head, Hilton Head Island, SC from $165

Luxury Villa Golf Beach & Pool Access Hilton Head

Oceanfront Condo 3 bed 3 bath sleeps 10
Hilton Head Island, SCrated 5.0
Oceanfront Resort. Newly Renovated 1BR Villa, Hilton Head Island, SC from $165

Oceanfront Resort. Newly Renovated 1BR Villa

Oceanfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Admiral's Row 339, Hilton Head Island, SC from $167

Admiral's Row 339

Beachfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Spacious Patio and Community Pool Access - Charming Family Retreat, Hilton Head Island, SC from $169

Spacious Patio and Community Pool Access - Charming Family Retreat

Oceanfront Condo 3 bed 2 bath sleeps 9
Hilton Head Island, SCrated 5.0
Breathtaking Views and Resort Amenities - Gorgeous Oceanfront Villa, Hilton Head Island, SC from $176

Breathtaking Views and Resort Amenities - Gorgeous Oceanfront Villa

Oceanfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Oceanfront Escape with Stunning Views and Pool - Serene Coastal Retreat, Hilton Head Island, SC from $179

Oceanfront Escape with Stunning Views and Pool - Serene Coastal Retreat

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Oceanfront Breakers 137 Condo w/ Sunrise Views!, Hilton Head Island, SC from $180

Oceanfront Breakers 137 Condo w/ Sunrise Views!

Oceanfront Entire condo 1 bed 1 bath sleeps 4
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 →

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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