Under $250 stays in Hilton Head Island

from $124

Spacious Villa with Scenic Balcony and Resort Access - Stylish Coastal Haven

Beachfront Condo 1 bed 1 bath sleeps 6

Hilton Head Island, SC

from $124

Coastal Escape w/ Pool & Ocean Peek!

Beachfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

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 $129

Fully Equipped Kitchen and Resort Amenities Await - Spacious Villa Retreat

Beachfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $131

Beachfront condo w pool, tennis and pickleball, gym & balcony

Beachfront 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 $134

Waterfront condo with seasonal pools, hot tub, balcony, AC, & WD

Waterfront Condo 1 bed 1 bath sleeps 4

Hilton Head Island, SC

from $136

Scenic Balcony and Resort Amenities - Charming Villa Retreat

Beachfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $138

Waterfront Condo with Ocean Views, Shared Pool, Hot Tub, and Covered Balcony

Waterfront Condo 1 bed 2 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

Waterfront condo with amazing views, on-site pool, hot tub, & gym

Waterfront Condo 2 bed 2 bath sleeps 6

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 $151

Updated, waterfront condo with amazing lagoon & golf views from the sunroom

Waterfront Condo 2 bed 2 bath sleeps 6 pets ok

Hilton Head Island, SC

from $151

Newly renovated beachfront condo with pool, tennis, restaurants, gym, & balcony

Beachfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $152

Tennis Villas B04

Beachfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $154

Tennis Villas F09

Beachfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $156

Waterfront, dog-friendly Villa at Shelter Cove with pool, deck & harbor view

Waterfront Villa 2 bed 2 bath sleeps 4 pets ok

Hilton Head Island, SC

from $158

Coastal Views and Direct Beach Access - Stunning Beachfront Retreat

Beachfront Condo 2 bed 2 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 $165

Dreamy condo on the beach with balcony view, shared pool, & charming decor

Beachfront 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 $176

Beachfront Getaway! Hilton Head Resort Condo

Beachfront Entire condo 2 bed 2 bath sleeps 4

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 $186

1609 Port Villa

Waterfront House 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 $208

Quiet Waterfront Condo with WiFi - Pools & Hot Tub On-Site

Waterfront Condo 2 bed 2 bath sleeps 7

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 $242

Admiral's Row 130

Beachfront Condo 2 bed 2 bath sleeps 6

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