Under $250 stays in Hilton Head Island

from $185

Pool Time & Island Vibes! Hilton Head Getaway

Waterfront Entire condo 1 bed 1 bath sleeps 4

Hilton Head Island, SCrated 5.0

from $200

2 Mi to Beach: Condo w/ Pool Access in Hilton Head

Oceanfront Entire condo 2 bed 2 bath sleeps 5

Hilton Head Island, SCrated 5.0

from $202

Breakers 328 Oceanfront Hilton Head Condo. Stunning Beach View & Pool

Oceanfront Apartment 1 bed 1 bath sleeps 4

Hilton Head Island, SCrated 5.0

from $205

5 Hickory Cove

Bayfront Villa 3 bed 4 bath sleeps 10 pets ok

Hilton Head Island, SCrated 5.0

from $208

Heron's Rest at Port Villas by AvantStay. Waterfront Cove + Dock + Deck. Walk to Beach + Sea Pines

Waterfront House 3 bed 3 bath sleeps 8 pets ok

Hilton Head Island, SCrated 5.0

from $214

Beachside Luxury Villa w/ Pool on Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 5.0

from $217

Stunning Ocean Views and Cozy Retreat - Exquisite Oceanfront Escape

Oceanfront Villa 1 bed 1 bath sleeps 4

Hilton Head Island, SCrated 5.0

from $218

4501 Island Club

Oceanfront Villa 2 bed 2 bath sleeps 7

Hilton Head Island, SCrated 5.0

from $220

Oceanfront Pools and Stunning Views - Exquisite Coastal Retreat

Oceanfront Villa 2 bed 2 bath sleeps 7

Hilton Head Island, SCrated 5.0

from $228

4202 Windsor Court North

Oceanfront Villa 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 5.0

from $230

Coastal Soul-Gorgeous Direct OceanFront!

Oceanfront Condo 1 bed 1 bath sleeps 6

Hilton Head Island, SCrated 5.0

from $232

Inviting Outdoor Oasis with Pool and Billiard Room - Charming Retreat

Waterfront House 3 bed 3 bath sleeps 8 pets ok

Hilton Head Island, SCrated 5.0

from $236

Expansive Balcony and Community Pool - Stunning Oceanfront Villa

Oceanfront Villa 2 bed 2 bath sleeps 7

Hilton Head Island, SCrated 5.0

from $243

Sea Pines 3BR. Beach & Harbour Town & Pool Access

Oceanfront House 3 bed 2 bath sleeps 8

Hilton Head Island, SCrated 5.0

from $243

2 Mi to Beach! Hilton Head Golf Escape w/ Balcony

Waterfront Entire condo 2 bed 2 bath sleeps 4 pets ok

Hilton Head Island, SCrated 5.0

from $77

Tennis Villa F14 - Beach and Pool

Oceanfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.9

from $98

Seaside 279

Oceanfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SCrated 4.9

from $100

Beachfront Villa W/ Pool & Tennis Hilton Head

Beachfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SCrated 4.9

from $101

Oceanfront Villa w/Pool & Beach Access Hilton Head

Oceanfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SCrated 4.9

from $106

Oceanfront Pool and Sunny Sun Deck - Unique Coastal Villa

Oceanfront Villa 1 bed 1 bath sleeps 4

Hilton Head Island, SCrated 4.9

from $106

Seaside 102

Oceanfront Condo 1 bed 1 bath sleeps 6

Hilton Head Island, SCrated 4.9

from $113

Coastal Retreat: 4th Floor Balcony & Sunrises

Beachfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.9

from $113

Renovated Luxury Villa w/ Patio & Pool Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 7

Hilton Head Island, SCrated 4.9

from $116

Community Pool and Scenic Balcony - Delightful Coastal Escape

Beachfront Villa 2 bed 2 bath sleeps 6 pets ok

Hilton Head Island, SCrated 4.9

from $118

Seaside 386

Oceanfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SCrated 4.9

from $123

SerenityByTheSea-Couples Retreat-King,Bikes,Chairs

Oceanfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SCrated 4.9

from $132

Beautiful Couples Retreat Oceanview w/new bikes&Ch

Oceanfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SCrated 4.9

from $138

7813 Centre Court

Beachfront Villa 2 bed 2 bath sleeps 8

Hilton Head Island, SCrated 4.9

from $145

Charming Oceanfront Escape with Heated Pools and Spa - Inviting Haven

Oceanfront Condo 2 bed 2 bath sleeps 7

Hilton Head Island, SCrated 4.9

from $147

Community Pool and Coastal Decor - Tranquil Island Escape

Oceanfront Villa 2 bed 2 bath sleeps 6 pets ok

Hilton Head Island, SCrated 4.9

from $148

Scenic Patio and Resort Amenities - Exquisite Coastal Retreat

Oceanfront Condo 3 bed 2 bath sleeps 6 pets ok

Hilton Head Island, SCrated 4.9

from $152

Breakers 220 Hilton Head. Oceanfront. Heated Pool. Elevator. Renovated

Oceanfront Apartment 1 bed 1 bath sleeps 4

Hilton Head Island, SCrated 4.9

from $153

Beachfront Access and Free Bicycles - Charming Coastal Haven

Beachfront Villa 1 bed 1 bath sleeps 4

Hilton Head Island, SCrated 4.9

from $156

Private Balcony and Resort Amenities - Charming Villa Retreat

Beachfront Condo 2 bed 2 bath sleeps 8

Hilton Head Island, SCrated 4.9

from $156

Spacious Pool Area and Ocean Access - Charming Coastal Haven

Oceanfront Villa 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.9

from $160

Waterfront Villa w/dock near Dining Hilton Head

Waterfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.9

from $161

Seaside 357

Oceanfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SCrated 4.9

from $165

Oceanfront Luxury Villa w/ Pool on Hilton Head

Oceanfront Condo 1 bed 2 bath sleeps 4

Hilton Head Island, SCrated 4.9

from $172

Luxury Waterfront Villa w/ Dock on Hilton Head

Waterfront Condo 2 bed 2 bath sleeps 4 pets ok

Hilton Head Island, SCrated 4.9

from $180

Beachfront Villa With Ocean Views Hilton Head

Beachfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.9

from $184

Serene Escape with Community Pool and Bicycles - Tranquil Oasis

Oceanfront Villa 2 bed 2 bath sleeps 6 pets ok

Hilton Head Island, SCrated 4.9

from $185

Oceanfront Villa, Pool Prime Location! Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 7

Hilton Head Island, SCrated 4.9

from $194

1608 Port Villa

Canal front House 3 bed 3 bath sleeps 8

Hilton Head Island, SCrated 4.9

from $206

Oceanfront Pool and Beach Cruisers - Exquisite Coastal Escape

Oceanfront Villa 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.9

from $208

Spacious Living and Two Oceanfront Pools - Gorgeous Ocean View Villa

Oceanfront Villa 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.9

from $215

Oceanfront Villa w/ Rooftop Pool on Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.9

from $219

Oceanfront Condo! Breakers 210 w/ Sunrise Views

Oceanfront Entire condo 1 bed 1 bath sleeps 4

Hilton Head Island, SCrated 4.9

from $78

Hilton Head Hideaway: Renovated 1BR Ocean Villa

Beachfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SCrated 4.8