Sleeps 8+ stays in Hilton Head Island

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

from $240

Rooftop Deck! Luxury Oceanfront Villa, Hilton Head

Oceanfront Condo 3 bed 3 bath sleeps 10

Hilton Head Island, SCrated 4.7

from $246

Oceanfront Pools and Fitness Center - Exquisite Coastal Villa

Oceanfront Villa 2 bed 2 bath sleeps 8

Hilton Head Island, SCrated 4.7

from $255

Panoramic Ocean Views and Sundeck - Charming Oceanfront Retreat

Oceanfront Villa 3 bed 3 bath sleeps 8

Hilton Head Island, SCrated 4.7

from $277

Oceanfront Pool and Stunning Views - Gorgeous Villa Retreat

Oceanfront Villa 3 bed 3 bath sleeps 8

Hilton Head Island, SCrated 4.7

from $338

Oceanfront Penthouse Villa w/ Balcony, Hilton Head

Oceanfront Condo 3 bed 3 bath sleeps 10

Hilton Head Island, SCrated 4.7

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

from $452

Oceanfront Pool and Stunning Views - Elegant Coastal Sanctuary

Oceanfront Villa 3 bed 3 bath sleeps 8

Hilton Head Island, SCrated 4.7

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

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

from $179

67 Night Heron @ Sea Pines - Waterfront Villa

Waterfront House 3 bed 2 bath sleeps 8

Hilton Head Island, SCrated 4.6

from $321

Oceanfront Pools and Breathtaking Views - Luxurious Beachfront Haven

Beachfront Villa 3 bed 3 bath sleeps 8

Hilton Head Island, SCrated 4.6

from $382

Luxury Beachfront Villa w/ Pool on Hilton Head

Beachfront Condo 3 bed 3 bath sleeps 10

Hilton Head Island, SCrated 4.6

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

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

from $458

Private Pool and Screened Porch - Beautiful Coastal Escape

Oceanfront House 3 bed 2 bath sleeps 8

Hilton Head Island, SCrated 4.6

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

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

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

from $206

Lagoon View and Resort Amenities - Elegant Beachfront Retreat

Beachfront Condo 2 bed 2 bath sleeps 8

Hilton Head Island, SCrated 4.5

from $317

Oceanfront Retreat with Lush Backyard - Tranquil Coastal Escape

Oceanfront House 3 bed 3 bath sleeps 8

Hilton Head Island, SCrated 4.5

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

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

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

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

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

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

from $1,606

10 Cassina Lane

Oceanfront House 5 bed 4.5 bath sleeps 12

Hilton Head Island, SCrated 3.4

from $124

Lagoon front, 3 story condo w balcony & washer dryer, snowbird-friendly

Bayfront Condo 3 bed 2 bath sleeps 10

Hilton Head Island, SC

from $125

Waterfront Condo with Shared Pools, Hot Tubs, Private Balconies, and Ocean Views

Waterfront Condo 2 bed 2 bath sleeps 8

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 $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 $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 $254

Beachfront escape with pools, hot tub, WiFi, washer dryer, & central AC

Beachfront Villa 2 bed 2 bath sleeps 8

Hilton Head Island, SC

from $254

Beachfront getaway with WiFi, pools, hot tub, gym, washer dryer, & central AC

Beachfront Villa 3 bed 3 bath sleeps 9

Hilton Head Island, SC

from $264

Upgraded condo on waterfront with pool, hot tub, & tennis access - near beach

Waterfront Condo 2 bed 2 bath sleeps 8

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

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 $298

Waterfront Getaway with Pools, Hot Tub, and Views of the Atlantic Ocean

Waterfront Condo 2 bed 2 bath sleeps 8

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 $329

Oceanfront Villa! Private Beach, Pool, Hilton Head

Beachfront Condo 3 bed 3 bath sleeps 9

Hilton Head Island, SC

from $339

Beachfront escape with pools, hot tub, athletic courts, WD, and central AC

Beachfront Condo 3 bed 3 bath sleeps 10

Hilton Head Island, SC

from $347

Renovated Sea Pines Home Near Beach

Waterfront House 3 bed 2 bath sleeps 8

Hilton Head Island, SC

from $359

Endless Tides - Marshfront Lands End Retreat. Pool Across Street. 500 Feet to Beach Access

Soundfront Townhouse 4 bed 3 bath sleeps 8

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