2 bedrooms stays in Hilton Head Island

137 two bedroom rentals in Hilton Head Island, SC, from $66 a night.

Rates are each listing's own "from" price on 4 August 2026; the booking page shows live prices and dates. Looking for the houses we would book ourselves? The curated Hilton Head Island list.

Showing 1 to 48 of 137, page 1 of 3. Best rated first, then price.

Waterfront condo with private balcony, W D and near beach and marina, Hilton Head Island, SC from $95

Waterfront condo with private balcony, W D and near beach and marina

Waterfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Beachside Bliss, Newly Renovated, Pet Friendly, Hilton Head Island, SC from $102

Beachside Bliss, Newly Renovated, Pet Friendly

Waterfront Condo 2 bed 2 bath sleeps 6 pets ok
Hilton Head Island, SCrated 5.0
736 Queens Grant @ Palmetto Dunes. Updated Condo. Prime Location, Hilton Head Island, SC from $106

736 Queens Grant @ Palmetto Dunes. Updated Condo. Prime Location

Oceanfront Condo 2 bed 1 bath sleeps 6
Hilton Head Island, SCrated 5.0
Admiral's Row. 3rd Floor Gem. Beachfront Balcony, Hilton Head Island, SC from $106

Admiral's Row. 3rd Floor Gem. Beachfront Balcony

Beachfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Charming Villa with Outdoor Courtyard - Cozy Coastal Escape, Hilton Head Island, SC from $111

Charming Villa with Outdoor Courtyard - Cozy Coastal Escape

Oceanfront Condo 2 bed 1 bath sleeps 6 pets ok
Hilton Head Island, SCrated 5.0
Queens Grant 655, Hilton Head Island, SC from $118

Queens Grant 655

Oceanfront Condo 2 bed 1 bath sleeps 5
Hilton Head Island, SCrated 5.0
Renovated Coastal Villa, Pet Friendly! Hilton Head, Hilton Head Island, SC from $120

Renovated Coastal Villa, Pet Friendly! Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 4 pets ok
Hilton Head Island, SCrated 5.0
Steps to Beach! 2BR Oceanfront Pool, Private Balcony & Coastal Charm, Hilton Head Island, SC from $121

Steps to Beach! 2BR Oceanfront Pool, Private Balcony & Coastal Charm

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Elegant Villa w/ Pool, Golf & Beach, Hilton Head, Hilton Head Island, SC from $122

Elegant Villa w/ Pool, Golf & Beach, Hilton Head

Oceanfront Condo 2 bed 1 bath sleeps 5
Hilton Head Island, SCrated 5.0
Beachfront condo with large furnished balcony, pool & beautiful views, Hilton Head Island, SC from $145

Beachfront condo with large furnished balcony, pool & beautiful views

Beachfront Condo 2 bed 2 bath sleeps 8
Hilton Head Island, SCrated 5.0
Coastal Luxury! Pool, Golf, Beach Hilton Head, Hilton Head Island, SC from $148

Coastal Luxury! Pool, Golf, Beach Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 7 pets ok
Hilton Head Island, SCrated 5.0
Palmetto Dunes Chic 2BR Villa Pickleball Golf Pool, Hilton Head Island, SC from $150

Palmetto Dunes Chic 2BR Villa Pickleball Golf Pool

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
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Coastal Chic Villa Near Beach and Shops, Hilton Head Island, SC from $156

Coastal Chic Villa Near Beach and Shops

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Forest Beach Condo. Community Pool. Oceanfront Private Beach Access. Elegant Furnishings, Hilton Head Island, SC from $163

Forest Beach Condo. Community Pool. Oceanfront Private Beach Access. Elegant Furnishings

Oceanfront Condo 2 bed 2 bath sleeps 4
Hilton Head Island, SCrated 5.0
Admiral's Row 339, Hilton Head Island, SC from $167

Admiral's Row 339

Beachfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Oceanfront Escape with Stunning Views and Pool - Serene Coastal Retreat, Hilton Head Island, SC from $179

Oceanfront Escape with Stunning Views and Pool - Serene Coastal Retreat

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
7447 Anchorage, Hilton Head Island, SC from $180

7447 Anchorage

Oceanfront Villa 2 bed 2 bath sleeps 6 pets ok
Hilton Head Island, SCrated 5.0
2 Mi to Beach: Condo w/ Pool Access in Hilton Head, Hilton Head Island, SC 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
Beachside Luxury Villa w/ Pool on Hilton Head, Hilton Head Island, SC from $214

Beachside Luxury Villa w/ Pool on Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
4501 Island Club, Hilton Head Island, SC from $218

4501 Island Club

Oceanfront Villa 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 5.0
Oceanfront Pools and Stunning Views - Exquisite Coastal Retreat, Hilton Head Island, SC from $220

Oceanfront Pools and Stunning Views - Exquisite Coastal Retreat

Oceanfront Villa 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 5.0
4202 Windsor Court North, Hilton Head Island, SC from $228

4202 Windsor Court North

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Expansive Balcony and Community Pool - Stunning Oceanfront Villa, Hilton Head Island, SC from $236

Expansive Balcony and Community Pool - Stunning Oceanfront Villa

Oceanfront Villa 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 5.0
2 Mi to Beach! Hilton Head Golf Escape w/ Balcony, Hilton Head Island, SC 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
Beachfront Access and Community Pool - Stunning Coastal Retreat, Hilton Head Island, SC from $258

Beachfront Access and Community Pool - Stunning Coastal Retreat

Beachfront Villa 2 bed 2 bath sleeps 8
Hilton Head Island, SCrated 5.0
Oceanfront Villa w/ Pool Beach Access Hilton Head, Hilton Head Island, SC from $298

Oceanfront Villa w/ Pool Beach Access Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Oceanfront Villa w/Wrap Around Balcony Hilton Head, Hilton Head Island, SC from $306

Oceanfront Villa w/Wrap Around Balcony Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 5.0
137 Shorewood, Hilton Head Island, SC from $353

137 Shorewood

Beachfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Stunning Villa with Direct Beach Access - Elegant Oceanfront Retreat, Hilton Head Island, SC from $370

Stunning Villa with Direct Beach Access - Elegant Oceanfront Retreat

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 5.0
Tennis Villa F14 - Beach and Pool, Hilton Head Island, SC from $77

Tennis Villa F14 - Beach and Pool

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Coastal Retreat: 4th Floor Balcony & Sunrises, Hilton Head Island, SC from $113

Coastal Retreat: 4th Floor Balcony & Sunrises

Beachfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Renovated Luxury Villa w/ Patio & Pool Hilton Head, Hilton Head Island, SC from $113

Renovated Luxury Villa w/ Patio & Pool Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 4.9
Community Pool and Scenic Balcony - Delightful Coastal Escape, Hilton Head Island, SC 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
7813 Centre Court, Hilton Head Island, SC from $138

7813 Centre Court

Beachfront Villa 2 bed 2 bath sleeps 8
Hilton Head Island, SCrated 4.9
Charming Oceanfront Escape with Heated Pools and Spa - Inviting Haven, Hilton Head Island, SC 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
Community Pool and Coastal Decor - Tranquil Island Escape, Hilton Head Island, SC 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
Private Balcony and Resort Amenities - Charming Villa Retreat, Hilton Head Island, SC from $156

Private Balcony and Resort Amenities - Charming Villa Retreat

Beachfront Condo 2 bed 2 bath sleeps 8
Hilton Head Island, SCrated 4.9
Spacious Pool Area and Ocean Access - Charming Coastal Haven, Hilton Head Island, SC 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
Waterfront Villa w/dock near Dining Hilton Head, Hilton Head Island, SC from $160

Waterfront Villa w/dock near Dining Hilton Head

Waterfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Luxury Waterfront Villa w/ Dock on Hilton Head, Hilton Head Island, SC 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
Beachfront Villa With Ocean Views Hilton Head, Hilton Head Island, SC from $180

Beachfront Villa With Ocean Views Hilton Head

Beachfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Serene Escape with Community Pool and Bicycles - Tranquil Oasis, Hilton Head Island, SC 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
Oceanfront Villa, Pool Prime Location! Hilton Head, Hilton Head Island, SC from $185

Oceanfront Villa, Pool Prime Location! Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 7
Hilton Head Island, SCrated 4.9
Oceanfront Pool and Beach Cruisers - Exquisite Coastal Escape, Hilton Head Island, SC from $206

Oceanfront Pool and Beach Cruisers - Exquisite Coastal Escape

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Spacious Living and Two Oceanfront Pools - Gorgeous Ocean View Villa, Hilton Head Island, SC 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
Oceanfront Villa w/ Rooftop Pool on Hilton Head, Hilton Head Island, SC from $215

Oceanfront Villa w/ Rooftop Pool on Hilton Head

Oceanfront Condo 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Oceanfront Pool and Luxurious Amenities - Serene Coastal Haven, Hilton Head Island, SC from $258

Oceanfront Pool and Luxurious Amenities - Serene Coastal Haven

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
Oceanfront Pool and Scenic Views - Stunning Coastal Haven, Hilton Head Island, SC from $318

Oceanfront Pool and Scenic Views - Stunning Coastal Haven

Oceanfront Villa 2 bed 2 bath sleeps 6
Hilton Head Island, SCrated 4.9
The curated list

Hilton Head Island the way we would book it: a short list of houses we checked for real water access.

Open the Hilton Head Island guide →
Every shore

Ten shores, each with its own stays list and curated picks.

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