2 bedrooms stays in Hilton Head Island

from $131

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

Beachfront Condo 2 bed 2 bath sleeps 6

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 $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 $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 $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 $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 $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 $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 $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 $253

Luxury Villa Rooftop Pool near Beach Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 6

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 $255

Ocean view condo at beachfront resort with pool, hot tub, pickleball & tennis

Beachfront Condo 2 bed 2 bath sleeps 6

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 $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

Charming waterfront resort condo with pool, tennis, golf, & balcony

Waterfront Condo 2 bed 2 bath sleeps 4

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 $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 $308

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

Oceanfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $328

51 Ocean Club

Beachfront Villa 2 bed 2 bath sleeps 6

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