Oceanfront stays in Hilton Head Island

from $100

Seaside 247

Oceanfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SC

from $111

Pet-Friendly Inverness Villa on Golf Course

Oceanfront Condo 2 bed 2 bath sleeps 6 pets ok

Hilton Head Island, SC

from $116

2BR Queen's Grant Villa in Palmetto Dunes, Modern Furnishings, Prime Location, Community Pool!

Oceanfront Villa 2 bed 1 bath sleeps 7 pets ok

Hilton Head Island, SC

from $117

Hilton Head Beach & Tennis Resort, Oceanfront, Tennis, Restaurants, Pickleball!

Oceanfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SC

from $119

Seaside 278

Oceanfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SC

from $121

Open and Airy 3 Bed 2 Bath St Andrews Villa

Oceanfront Condo 2 bed 2 bath sleeps 6 pets ok

Hilton Head Island, SC

from $122

Oceanfront condo with WiFi, pool, hot tub & beach access

Oceanfront Condo 2 bed 2 bath sleeps 5

Hilton Head Island, SC

from $123

Spacious Patio and Community Pool - Elegant Coastal Hideaway

Oceanfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $132

Beach-view condo in oceanfront complex with outdoor pool, beach access, balcony

Oceanfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SC

from $139

Seaside 358

Oceanfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SC

from $140

Beach-view condo in oceanfront complex with outdoor pool, beach access & balcony

Oceanfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SC

from $143

Oceanfront, 3rd floor villa with corner balcony, pool and beach access

Oceanfront Villa 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $143

Panoramic Views and Luxurious Amenities - Stunning Oceanfront Retreat

Oceanfront Condo 1 bed 1 bath sleeps 6

Hilton Head Island, SC

from $143

Dont Worry, Beach Happy 1BR Oceanview King Bed Villa in HHBT Resort

Oceanfront Villa 1 bed 1 bath sleeps 4

Hilton Head Island, SC

from $144

Calming Condo Getaway with Shared Pool, Hot Tub, and Tennis Courts

Oceanfront Condo 2 bed 2 bath sleeps 7

Hilton Head Island, SC

from $148

Stunning Views and Resort Amenities - Charming Oceanfront Haven

Oceanfront Condo 1 bed 1 bath sleeps 6

Hilton Head Island, SC

from $161

Beach-view condo in oceanfront complex with outdoor pool, beach access & balcony

Oceanfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SC

from $162

Gorgeous Oceanfront Villa, w/ Pool on Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $166

Oceanfront villa with WiFi, full kitchen, pool, & hot tub - beach nearby

Oceanfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $179

Oceanfront Villa with Shared Pool, Hot Tub, Ocean Views, and More - Beach Nearby

Oceanfront Condo 3 bed 3 bath sleeps 8

Hilton Head Island, SC

from $183

309 Breakers

Oceanfront Villa 1 bed 1 bath sleeps 6

Hilton Head Island, SC

from $186

Oceanfront Condo with Shared Pool, Hot Tub, Beach Access & Playground

Oceanfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $190

Amazing oceanfront 2BR 2BA 1st floor condo with pool, hot tub, tennis, fitness area, & WD

Oceanfront Condo 2 bed 2 bath sleeps 7

Hilton Head Island, SC

from $192

Peaceful Oceanfront Villa with Pools, Hot Tub, Tennis, & Ocean View

Oceanfront Condo 2 bed 2 bath sleeps 7

Hilton Head Island, SC

from $193

2BR Beach Villa with Balcony Pool Tennis Access

Oceanfront Apartment 2 bed 2 bath sleeps 5

Hilton Head Island, SC

from $194

Oceanfront condo with a washer, dryer, central AC, pool, hot tub & beach access

Oceanfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $202

231 Breakers

Oceanfront Villa 1 bed 1 bath sleeps 5

Hilton Head Island, SC

from $216

A Quiet Beach Getaway with Pools, Hot Tub, Tennis Courts, and Private Patio

Oceanfront Condo 2 bed 2 bath sleeps 5

Hilton Head Island, SC

from $221

First Floor, Oceanfront Condo with Free WiFi, Balcony, Shared Hot Tub, Pool, Sauna

Oceanfront House 2 bed 2 bath sleeps 8

Hilton Head Island, SC

from $223

Oceanfront Condo with Ocean View, Shared Pool Hot Tub, and Nearby Beach Access

Oceanfront Condo 3 bed 3 bath sleeps 8

Hilton Head Island, SC

from $236

Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access

Oceanfront Apartment 1 bed 1 bath sleeps 4

Hilton Head Island, SC

from $242

A Relaxing Getaway with Shared Pools and Hot Tub in an Oceanfront Villa

Oceanfront Condo 2 bed 2 bath sleeps 4

Hilton Head Island, SC

from $243

Splendid condo, pool, full kitchen, & patio

Oceanfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $245

Spacious updated oceanfront condo with shared pools, hot tub & beach access

Oceanfront Condo 2 bed 2 bath sleeps 8

Hilton Head Island, SC

from $247

Oceanfront condo with pools, hot tubs, WiFi, washer, dryer, & central AC

Oceanfront Condo 3 bed 3 bath sleeps 10

Hilton Head Island, SC

from $253

Luxury Villa Rooftop Pool near Beach Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $271

Oceanfront Villa with Ocean Views, Shared Pool Hot Tub, and Nearby Beach Access

Oceanfront Condo 3 bed 3 bath sleeps 8

Hilton Head Island, SC

from $288

Oceanfront Villa with Shared Pools, Hot tub, and Beach Access

Oceanfront Condo 2 bed 2 bath sleeps 8

Hilton Head Island, SC

from $291

Cozy oceanfront villa, tennis courts, hot tub, shared pool and ocean view

Oceanfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $291

Newly-renovated ocean front condo on the 5th floor with a private balcony

Oceanfront Condo 2 bed 2 bath sleeps 8

Hilton Head Island, SC

from $308

Oceanfront condo with pools, hot tubs, fitness room, & central AC

Oceanfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $314

Stunning oceanfront villa with WiFi, pool & hot tub, private balcony

Oceanfront Condo 3 bed 3 bath sleeps 7

Hilton Head Island, SC

from $325

Oceanfront with Views! Pool & Beach on Hilton Head

Oceanfront Condo 3 bed 3 bath sleeps 10

Hilton Head Island, SC

from $348

Sunlit Oceanfront Condo with Two Balconies, Wet Bar, Beach Views & WiFi

Oceanfront Condo 3 bed 3 bath sleeps 6

Hilton Head Island, SC

from $370

Oceanfront Villa with kitchen, balcony, patio shared pool and trails

Oceanfront Villa 4 bed 4 bath sleeps 10

Hilton Head Island, SC

from $378

Stunning Oceanfront Villa - 3rd Floor Views and Renovated 2026

Oceanfront Apartment 2 bed 2 bath sleeps 5

Hilton Head Island, SC

from $388

Exquisite oceanfront top-floor condo has the feel of paradise on earth

Oceanfront Condo 2 bed 2 bath sleeps 7

Hilton Head Island, SC

from $407

Serene Oceanfront Villa with WiFi, Pool, Hot Tub, & Fitness Center

Oceanfront Condo 3 bed 3 bath sleeps 7

Hilton Head Island, SC