2 bedrooms stays in Hilton Head Island

from $339

Oceanfront Escape with Pools and Hot Tub - Stunning Coastal Haven

Oceanfront Vacation Rental 2 bed 1 bath sleeps 6

Hilton Head Island, SCrated 4.9

from $397

Breathtaking Ocean Views and Resort Style Pools - Amazing Beachfront Oasis

Beachfront Condo 2 bed 2 bath sleeps 5

Hilton Head Island, SCrated 4.9

from $98

Modern Beachfront Bliss: 2BR/2BA Luxury Villa

Beachfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.8

from $100

Beachfront Cabana and Two Pools - Spacious Coastal Escape

Beachfront Villa 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.8

from $121

Admiral's Row 309: Beachfront Luxury Living

Beachfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.8

from $155

Balcony Overlooking Tennis Courts and Resort Amenities - Charming Villa Escape

Beachfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.8

from $200

Oceanfront Pool and Spa Retreat - Amazing Ocean Views and Spacious Comfort

Oceanfront Villa 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.8

from $207

Luxury Beachfront Villa w/ Pool, on Hilton Head

Beachfront Condo 2 bed 2 bath sleeps 8

Hilton Head Island, SCrated 4.8

from $273

Oceanfront Pool and Beach Cruiser Bicycles - Stunning Coastal Haven

Oceanfront Villa 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.8

from $280

Oceanfront Access and Community Pool - Beautiful Coastal Haven

Oceanfront Villa 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.8

from $322

Oceanfront with Pool & Beach Access Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.8

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 $101

Shipmaster Villa 801 - Perfect Beach and Golf

Oceanfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.6

from $173

Closest 2 BR to the Beach! Hilton Head Condo

Beachfront Entire condo 2 bed 2 bath sleeps 4

Hilton Head Island, SCrated 4.6

from $213

Oceanfront Pools and Cozy Decor - Charming Villa Escape

Oceanfront Villa 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.6

from $232

Oceanfront Pool and Free Bikes - Inviting Coastal Haven

Oceanfront Villa 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.6

from $330

Ocean Views and Community Pool - Stunning Oceanfront Retreat

Oceanfront Villa 2 bed 2 bath sleeps 7

Hilton Head Island, SCrated 4.6

from $95

Coastal 2BR Villa Near Beach & Golf in Palmetto

Oceanfront Condo 2 bed 2 bath sleeps 4

Hilton Head Island, SCrated 4.5

from $165

1981 St. Andrews Common

Oceanfront Villa 2 bed 2 bath sleeps 5 pets ok

Hilton Head Island, SCrated 4.5

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 $209

Family-Friendly Condo w/ Pools + Tennis Courts!

Oceanfront Entire condo 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.5

from $285

1611 Port Villa @ South Beach - Waterfront Villa

Waterfront House 2 bed 2 bath sleeps 6

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 $205

Oceanfront Access and Community Pool - Beautiful Coastal Villa

Oceanfront Villa 2 bed 2 bath sleeps 5

Hilton Head Island, SCrated 4.4

from $206

Long-Term Stays Welcome: HH Island Resort Condo

Oceanfront Entire condo 2 bed 2 bath sleeps 7

Hilton Head Island, SCrated 4.4

from $91

Waterfront Villa! Near Pool & Tennis, Hilton Head

Waterfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.3

from $117

Dream Getaway w/ wraparound deck on Hilton Head!

Oceanfront Condo 2 bed 2 bath sleeps 5 pets ok

Hilton Head Island, SCrated 4.0

from $137

Oceanfront Resort with Tennis Pool Spa

Oceanfront Apartment 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 4.0

from $203

Beach & Pool Access: Tranquil Hilton Head Getaway

Beachfront Entire condo 2 bed 2 bath sleeps 5

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 $255

Pool Access: Beachfront Hilton Head Resort Condo

Beachfront Entire condo 2 bed 2 bath sleeps 6

Hilton Head Island, SCrated 3.5

from $66

Beachfront villa near golf with pool, hot tub, & balcony - snowbird-friendly

Beachfront Villa 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $79

3rd Floor Condo with pools, tennis/pickleball courts, access to beach

Beachfront Condo 2 bed 2 bath sleeps 4

Hilton Head Island, SC

from $98

Perfectly Located Family Condo with Shared Pool, Central AC, Private Washer and dryer, Free WiFi

Bayfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $98

Oceanview 4th Floor. 2BR Beach & Tennis Villa

Beachfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $104

Waterfront villa with resort amenities, beach access, open layout, AC, & WD

Waterfront Villa 2 bed 2 bath sleeps 6

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 $116

Condo near beach with 2 pools, restaurants, gym, 6 tennis, 12 pickleball, W D

Beachfront Condo 2 bed 2 bath sleeps 6

Hilton Head Island, SC

from $117

Waterfront condo with walkable locale, central AC, washer dryer, & shared pool

Waterfront Condo 2 bed 2 bath sleeps 7

Hilton Head Island, SC

from $118

Pet Friendly Villa with Patio, Pool, + Nearby Golf

Beachfront Condo 2 bed 1 bath sleeps 5 pets ok

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 $124

Beachfront Getaway. Pool, Tennis + Ocean Air

Beachfront Condo 2 bed 2 bath sleeps 5

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 $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