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 193 to 240 of 337, page 5 of 8. Best rated first, then price.

Private Pool and Screened Porch - Beautiful Coastal Escape, Hilton Head Island, SC from $458

Private Pool and Screened Porch - Beautiful Coastal Escape

Oceanfront House 3 bed 2 bath sleeps 8
Hilton Head Island, SCrated 4.6
Private Pool and Glorious Ocean Views - Exquisite Beachfront Haven, Hilton Head Island, SC from $1,341

Private Pool and Glorious Ocean Views - Exquisite Beachfront Haven

Beachfront House 8 bed 7 bath sleeps 21
Hilton Head Island, SCrated 4.6
In-Ground Pool and Ocean Views - Elegant Beachfront Retreat, Hilton Head Island, SC from $1,407

In-Ground Pool and Ocean Views - Elegant Beachfront Retreat

Beachfront House 8 bed 9.5 bath sleeps 26
Hilton Head Island, SCrated 4.6
Ocean Access and Private Pool - Stunning Coastal Sanctuary, Hilton Head Island, SC from $1,654

Ocean Access and Private Pool - Stunning Coastal Sanctuary

Oceanfront House 6 bed 7 bath sleeps 18
Hilton Head Island, SCrated 4.6
Coastal 2BR Villa Near Beach & Golf in Palmetto, Hilton Head Island, SC from $95

Coastal 2BR Villa Near Beach & Golf in Palmetto

Oceanfront Condo 2 bed 2 bath sleeps 4
Hilton Head Island, SCrated 4.5
Scenic Balcony and Resort Amenities - Charming Retreat, Hilton Head Island, SC from $112

Scenic Balcony and Resort Amenities - Charming Retreat

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.5
Balcony and Access to Beach and Tennis Courts - Spacious Coastal Oasis, Hilton Head Island, SC from $123

Balcony and Access to Beach and Tennis Courts - Spacious Coastal Oasis

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.5
Oceanfront Villa and Bicycles - Stunning Coastal Escape, Hilton Head Island, SC from $156

Oceanfront Villa and Bicycles - Stunning Coastal Escape

Oceanfront Villa 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.5
1981 St. Andrews Common, Hilton Head Island, SC from $165

1981 St. Andrews Common

Oceanfront Villa 2 bed 2 bath sleeps 5 pets ok
Hilton Head Island, SCrated 4.5
Oceanfront Villa with Beach Chairs and Bicycles - Stunning Coastal Retreat, Hilton Head Island, SC from $200

Oceanfront Villa with Beach Chairs and Bicycles - Stunning Coastal Retreat

Oceanfront Villa 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.5
Lagoon View and Resort Amenities - Elegant Beachfront Retreat, Hilton Head Island, SC from $206

Lagoon View and Resort Amenities - Elegant Beachfront Retreat

Beachfront Condo 2 bed 2 bath sleeps 8
Hilton Head Island, SCrated 4.5
Family-Friendly Condo w/ Pools + Tennis Courts!, Hilton Head Island, SC from $209

Family-Friendly Condo w/ Pools + Tennis Courts!

Oceanfront Entire condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.5
Compare before you book

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

Search Vrbo → Booking.com → Affiliate links.
Oceanfront Villa and Stunning Views - Luxurious Coastal Retreat, Hilton Head Island, SC from $247

Oceanfront Villa and Stunning Views - Luxurious Coastal Retreat

Oceanfront Villa 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.5
1611 Port Villa @ South Beach - Waterfront Villa, Hilton Head Island, SC from $285

1611 Port Villa @ South Beach - Waterfront Villa

Waterfront House 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.5
Oceanfront Retreat with Lush Backyard - Tranquil Coastal Escape, Hilton Head Island, SC from $317

Oceanfront Retreat with Lush Backyard - Tranquil Coastal Escape

Oceanfront House 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 4.5
Private Pool and Spa Oasis - Spacious Family Retreat with Entertainment, Hilton Head Island, SC from $391

Private Pool and Spa Oasis - Spacious Family Retreat with Entertainment

Oceanfront House 5 bed 4 bath sleeps 22 pets ok
Hilton Head Island, SCrated 4.5
Pet Friendly Villa, Pool Beach & Golf! Hilton Head, Hilton Head Island, SC from $125

Pet Friendly Villa, Pool Beach & Golf! Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 8 pets ok
Hilton Head Island, SCrated 4.4
Waterfront Villa w/ Dock Near Beach on Hilton Head, Hilton Head Island, SC from $199

Waterfront Villa w/ Dock Near Beach on Hilton Head

Waterfront Condo 3 bed 3 bath sleeps 6 pets ok
Hilton Head Island, SCrated 4.4
Oceanfront Access and Community Pool - Beautiful Coastal Villa, Hilton Head Island, SC from $205

Oceanfront Access and Community Pool - Beautiful Coastal Villa

Oceanfront Villa 2 bed 2 bath sleeps 5
Hilton Head Island, SCrated 4.4
Long-Term Stays Welcome: HH Island Resort Condo, Hilton Head Island, SC from $206

Long-Term Stays Welcome: HH Island Resort Condo

Oceanfront Entire condo 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 4.4
Oceanfront Pool and Beach Access - Exquisite Family Retreat, Hilton Head Island, SC from $2,195

Oceanfront Pool and Beach Access - Exquisite Family Retreat

Oceanfront House 8 bed 11 bath sleeps 24
Hilton Head Island, SCrated 4.4
Waterfront Villa! Near Pool & Tennis, Hilton Head, Hilton Head Island, SC from $91

Waterfront Villa! Near Pool & Tennis, Hilton Head

Waterfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.3
Fun Oceanfront Villa w/ Pool on Hilton Head, Hilton Head Island, SC from $107

Fun Oceanfront Villa w/ Pool on Hilton Head

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.3
Beach Access: Oceanfront Hilton Head Studio, Hilton Head Island, SC from $136

Beach Access: Oceanfront Hilton Head Studio

Oceanfront Entire loft 1 bath sleeps 4
Hilton Head Island, SCrated 4.3
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 6
Hilton Head Island, SCrated 4.0
Beachside Condo with Shared Pool & Private Balcony Retreat, Hilton Head Island, SC from $116

Beachside Condo with Shared Pool & Private Balcony Retreat

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.0
Dream Getaway w/ wraparound deck on Hilton Head!, Hilton Head Island, SC from $117

Dream Getaway w/ wraparound deck on Hilton Head!

Oceanfront Condo 2 bed 2 bath sleeps 5 pets ok
Hilton Head Island, SCrated 4.0
Balcony, Ocean Access and Spacious Living Area - Charming Coastal Haven, Hilton Head Island, SC from $124

Balcony, Ocean Access and Spacious Living Area - Charming Coastal Haven

Beachfront Condo 1 bed 1 bath sleeps 5
Hilton Head Island, SCrated 4.0
Oceanfront Resort with Tennis Pool Spa, Hilton Head Island, SC from $137

Oceanfront Resort with Tennis Pool Spa

Oceanfront Apartment 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.0
Harbourfront Condo in Harbour Town, Hilton Head Island, SC from $152

Harbourfront Condo in Harbour Town

Harbor front Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 4.0
Beach & Pool Access: Tranquil Hilton Head Getaway, Hilton Head Island, SC from $203

Beach & Pool Access: Tranquil Hilton Head Getaway

Beachfront Entire condo 2 bed 2 bath sleeps 5
Hilton Head Island, SCrated 4.0
Ocean Villas C346, Hilton Head Island, SC from $243

Ocean Villas C346

Beachfront Condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 4.0
Luxury Coastal Home, Pool & Hot Tub on Hilton Head, Hilton Head Island, SC from $304

Luxury Coastal Home, Pool & Hot Tub on Hilton Head

Oceanfront House 3 bed 2 bath sleeps 8
Hilton Head Island, SCrated 4.0
Exquisite Home w/ Private Pool & Dock Hilton Head, Hilton Head Island, SC from $597

Exquisite Home w/ Private Pool & Dock Hilton Head

Canal front House 4 bed 3 bath sleeps 8
Hilton Head Island, SCrated 4.0
Pool, Spa & Dining: Beach Condo in Hilton Head!, Hilton Head Island, SC from $107

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

Beachfront Entire condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 3.7
Community Swimming Pool and Free Bikes - Charming Island Haven, Hilton Head Island, SC from $208

Community Swimming Pool and Free Bikes - Charming Island Haven

Oceanfront Villa 2 bed 3 bath sleeps 8 pets ok
Hilton Head Island, SCrated 3.7
Pool Access: Beachfront Hilton Head Resort Condo, Hilton Head Island, SC from $255

Pool Access: Beachfront Hilton Head Resort Condo

Beachfront Entire condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 3.5
10 Cassina Lane, Hilton Head Island, SC from $1,606

10 Cassina Lane

Oceanfront House 5 bed 4.5 bath sleeps 12
Hilton Head Island, SCrated 3.4
Top Floor Condo at Beach & Tennis Resort Beachfront Pool & Golf access, Hilton Head Island, SC from $87

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

Beachfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 3.0
Panoramic Views and Luxurious Features - Stunning Oceanfront Villa, Hilton Head Island, SC from $136

Panoramic Views and Luxurious Features - Stunning Oceanfront Villa

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SCrated 3.0
Pool Access! Oceanfront Hilton Head Island Condo, Hilton Head Island, SC from $160

Pool Access! Oceanfront Hilton Head Island Condo

Oceanfront Entire condo 1 bed 1 bath sleeps 6
Hilton Head Island, SCrated 3.0
Pet Friendly Waterfront Villa w/ Dock, Hilton Head, Hilton Head Island, SC 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
Beachfront villa near golf with pool, hot tub, & balcony - snowbird-friendly, Hilton Head Island, SC from $66

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

Beachfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SC
Oceanfront resort condo with WiFi, balcony, pool, grills, & beach access, Hilton Head Island, SC from $78

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

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SC
3rd Floor Condo with pools, tennis/pickleball courts, access to beach, Hilton Head Island, SC from $79

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

Beachfront Condo 2 bed 2 bath sleeps 4
Hilton Head Island, SC
Secluded & Peaceful - Vacation Getaway with WiFi, Pool, Hot Tub, & Private Beach, Hilton Head Island, SC from $97

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

Beachfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SC
Perfectly Located Family Condo with Shared Pool, Central AC, Private Washer and dryer, Free WiFi, Hilton Head Island, SC from $98

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

Bayfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SC
Spacious condo with pool, tennis courts, & golf on-site, Hilton Head Island, SC from $98

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

Oceanfront Condo 1 bed 1 bath sleeps 4
Hilton Head Island, SC
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.

Get new posts in your inbox. No spam, unsubscribe anytime.