Sleeps 8+ stays in Hilton Head Island

103 sleeps eight or more rentals in Hilton Head Island, SC, from $98 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 103, page 1 of 3. Best rated first, then price.

Nautical touches abound at this renovated waterfront condo with pool & tennis, Hilton Head Island, SC from $98

Nautical touches abound at this renovated waterfront condo with pool & tennis

Waterfront Condo 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 5.0
Charming Oasis with Outdoor Patio and Resort Amenities - Cozy Retreat, Hilton Head Island, SC from $125

Charming Oasis with Outdoor Patio and Resort Amenities - Cozy Retreat

Oceanfront Condo 3 bed 3 bath sleeps 12 pets ok
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
Luxury Villa Golf Beach & Pool Access Hilton Head, Hilton Head Island, SC from $165

Luxury Villa Golf Beach & Pool Access Hilton Head

Oceanfront Condo 3 bed 3 bath sleeps 10
Hilton Head Island, SCrated 5.0
Spacious Patio and Community Pool Access - Charming Family Retreat, Hilton Head Island, SC from $169

Spacious Patio and Community Pool Access - Charming Family Retreat

Oceanfront Condo 3 bed 2 bath sleeps 9
Hilton Head Island, SCrated 5.0
5 Hickory Cove, Hilton Head Island, SC from $205

5 Hickory Cove

Bayfront Villa 3 bed 4 bath sleeps 10 pets ok
Hilton Head Island, SCrated 5.0
Heron's Rest at Port Villas by AvantStay. Waterfront Cove + Dock + Deck. Walk to Beach + Sea Pines, Hilton Head Island, SC 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
Inviting Outdoor Oasis with Pool and Billiard Room - Charming Retreat, Hilton Head Island, SC 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
Sea Pines 3BR. Beach & Harbour Town & Pool Access, Hilton Head Island, SC from $243

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

Oceanfront House 3 bed 2 bath sleeps 8
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
Stylish Dog-Friendly Oasis Near Beach & Lagoon, Hilton Head Island, SC from $313

Stylish Dog-Friendly Oasis Near Beach & Lagoon

Oceanfront House 4 bed 2 bath sleeps 10 pets ok
Hilton Head Island, SCrated 5.0
Steps to Beach! Oceanfront Hilton Head Villa, Pool, Hilton Head Island, SC from $313

Steps to Beach! Oceanfront Hilton Head Villa, Pool

Oceanfront Condo 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 5.0
Compare before you book

See Hilton Head Island on Vrbo, with dates and live prices.

Search Vrbo → Booking.com → Affiliate links.
Ocean Views and Zero-Entry Pool - Charming Oceanfront Retreat, Hilton Head Island, SC from $314

Ocean Views and Zero-Entry Pool - Charming Oceanfront Retreat

Oceanfront Condo 3 bed 3 bath sleeps 10
Hilton Head Island, SCrated 5.0
Private Pool Retreat on One Level. 2 Living Areas. Pet Friendly. Near Palmetto Dunes Beaches, Hilton Head Island, SC from $327

Private Pool Retreat on One Level. 2 Living Areas. Pet Friendly. Near Palmetto Dunes Beaches

Oceanfront House 4 bed 3 bath sleeps 9 pets ok
Hilton Head Island, SCrated 5.0
Oceanfront Access and Spacious Deck - Elegant Coastal Retreat, Hilton Head Island, SC from $331

Oceanfront Access and Spacious Deck - Elegant Coastal Retreat

Oceanfront Villa 4 bed 4 bath sleeps 8
Hilton Head Island, SCrated 5.0
Rooftop Sun Deck! Luxury Hilton Head Villa w/ Pool, Hilton Head Island, SC from $342

Rooftop Sun Deck! Luxury Hilton Head Villa w/ Pool

Oceanfront Condo 3 bed 3 bath sleeps 9
Hilton Head Island, SCrated 5.0
Luxurious Pool and Spa with Lagoon Access - Gorgeous Family Getaway, Hilton Head Island, SC from $349

Luxurious Pool and Spa with Lagoon Access - Gorgeous Family Getaway

Canal front House 4 bed 4 bath sleeps 12
Hilton Head Island, SCrated 5.0
Charming Lakefront Retreat in Palmetto Dunes!, Hilton Head Island, SC from $361

Charming Lakefront Retreat in Palmetto Dunes!

Lakefront Entire home 3 bed 2 bath sleeps 8
Hilton Head Island, SCrated 5.0
Beachside Luxury Villa, Pool & Spa, on Hilton Head, Hilton Head Island, SC from $409

Beachside Luxury Villa, Pool & Spa, on Hilton Head

Oceanfront Condo 3 bed 3 bath sleeps 10
Hilton Head Island, SCrated 5.0
Oceanfront Villa w/Pool Beach Access Hilton Head, Hilton Head Island, SC from $426

Oceanfront Villa w/Pool Beach Access Hilton Head

Oceanfront Condo 3 bed 3 bath sleeps 10
Hilton Head Island, SCrated 5.0
Extravagant Hilton Head Luxury Home Private Pool, Hilton Head Island, SC from $530

Extravagant Hilton Head Luxury Home Private Pool

Oceanfront House 3 bed 4 bath sleeps 10
Hilton Head Island, SCrated 5.0
Private Marshfront Oasis w/ Pool & Sunset Views, Hilton Head Island, SC from $557

Private Marshfront Oasis w/ Pool & Sunset Views

Soundfront House 4 bed 4 bath sleeps 8
Hilton Head Island, SCrated 5.0
Luxury Oceanfront Villa w/ Pool & Spa Hilton Head, Hilton Head Island, SC from $569

Luxury Oceanfront Villa w/ Pool & Spa Hilton Head

Oceanfront Condo 4 bed 4 bath sleeps 12
Hilton Head Island, SCrated 5.0
Private Patio and Community Pool - Exquisite Oceanfront Retreat, Hilton Head Island, SC from $575

Private Patio and Community Pool - Exquisite Oceanfront Retreat

Oceanfront Condo 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 5.0
Private Pool and Spa with Outdoor Kitchen - Luxurious Family Retreat, Hilton Head Island, SC from $718

Private Pool and Spa with Outdoor Kitchen - Luxurious Family Retreat

Oceanfront House 5 bed 4.5 bath sleeps 14
Hilton Head Island, SCrated 5.0
135 Mooring Buoy, Hilton Head Island, SC from $754

135 Mooring Buoy

Bayfront House 5 bed 6 bath sleeps 14 pets ok
Hilton Head Island, SCrated 5.0
Massive Luxury Beach Home Private Pool Hilton Head, Hilton Head Island, SC from $777

Massive Luxury Beach Home Private Pool Hilton Head

Beachfront House 6 bed 5 bath sleeps 18
Hilton Head Island, SCrated 5.0
Expansive Backyard Oasis and Upper Sun Terrace - Exquisite Coastal Retreat, Hilton Head Island, SC from $825

Expansive Backyard Oasis and Upper Sun Terrace - Exquisite Coastal Retreat

Beachfront House 6 bed 1 bath sleeps 14
Hilton Head Island, SCrated 5.0
Spacious Home with Pool and Spa - Elegant Coastal Retreat, Hilton Head Island, SC from $973

Spacious Home with Pool and Spa - Elegant Coastal Retreat

Oceanfront House 6 bed 6 bath sleeps 16
Hilton Head Island, SCrated 5.0
Oceanfront 5BR, Private Pool, Sleeps 13, Upper Balcony Views, in Forest Beach, Hilton Head Island, SC from $1,055

Oceanfront 5BR, Private Pool, Sleeps 13, Upper Balcony Views, in Forest Beach

Oceanfront House 5 bed 5 bath sleeps 13
Hilton Head Island, SCrated 5.0
Luxury Pool and Spa Oasis - Stunning Oceanfront Escape, Hilton Head Island, SC from $1,338

Luxury Pool and Spa Oasis - Stunning Oceanfront Escape

Oceanfront House 6 bed 5 bath sleeps 14
Hilton Head Island, SCrated 5.0
Private Pool, Outdoor Hot Tub, Gourmet Kitchen - Stunning Retreat, Hilton Head Island, SC from $1,380

Private Pool, Outdoor Hot Tub, Gourmet Kitchen - Stunning Retreat

Beachfront House 6 bed 6 bath sleeps 12
Hilton Head Island, SCrated 5.0
Heated Pool and Spa with Private Beach Access - Stunning Oceanfront Escape, Hilton Head Island, SC from $1,415

Heated Pool and Spa with Private Beach Access - Stunning Oceanfront Escape

Oceanfront House 8 bed 7 bath sleeps 19
Hilton Head Island, SCrated 5.0
Luxurious Oceanfront Haven with Huge Pool and Entertainment Area - Exquisite Retreat, Hilton Head Island, SC from $2,901

Luxurious Oceanfront Haven with Huge Pool and Entertainment Area - Exquisite Retreat

Oceanfront House 6 bed 7 bath sleeps 24
Hilton Head Island, SCrated 5.0
Oceanfront Paradise with Pool and Spa - Stunning Coastal Retreat, Hilton Head Island, SC from $2,922

Oceanfront Paradise with Pool and Spa - Stunning Coastal Retreat

Beachfront House 7 bed 8 bath sleeps 26
Hilton Head Island, SCrated 5.0
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
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
1608 Port Villa, Hilton Head Island, SC from $194

1608 Port Villa

Canal front House 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 4.9
Oceanfront Balcony and Spacious Living Areas - Stunning Coastal Haven, Hilton Head Island, SC from $448

Oceanfront Balcony and Spacious Living Areas - Stunning Coastal Haven

Oceanfront Villa 3 bed 3.5 bath sleeps 8
Hilton Head Island, SCrated 4.9
Stylish Sea Pines Home Hot Tub, Hilton Head, Hilton Head Island, SC from $477

Stylish Sea Pines Home Hot Tub, Hilton Head

Waterfront House 4 bed 3 bath sleeps 8
Hilton Head Island, SCrated 4.9
Private Pool and Games Room Retreat - Gorgeous Marshside Haven, Hilton Head Island, SC from $505

Private Pool and Games Room Retreat - Gorgeous Marshside Haven

Soundfront House 4 bed 3 bath sleeps 13
Hilton Head Island, SCrated 4.9
Oceanfront Access and Stunning Views - Amazing Coastal Escape, Hilton Head Island, SC from $1,583

Oceanfront Access and Stunning Views - Amazing Coastal Escape

Oceanfront House 7 bed 7.5 bath sleeps 20 pets ok
Hilton Head Island, SCrated 4.9
Scenic Deck and Access to Community Pool - Tranquil Villa Haven, Hilton Head Island, SC from $132

Scenic Deck and Access to Community Pool - Tranquil Villa Haven

Oceanfront Villa 3 bed 2.5 bath sleeps 8
Hilton Head Island, SCrated 4.8
Luxury Beachfront Villa w/ Pool, on Hilton Head, Hilton Head Island, SC from $207

Luxury Beachfront Villa w/ Pool, on Hilton Head

Beachfront Condo 2 bed 2 bath sleeps 8
Hilton Head Island, SCrated 4.8
Pools + Sundeck: Beachfront Hilton Head Condo!, Hilton Head Island, SC from $250

Pools + Sundeck: Beachfront Hilton Head Condo!

Beachfront Entire condo 3 bed 2 bath sleeps 9
Hilton Head Island, SCrated 4.8
Charming Coastal Haven with Game Room and Screened Porch - Unique Escape, Hilton Head Island, SC from $259

Charming Coastal Haven with Game Room and Screened Porch - Unique Escape

Waterfront House 4 bed 3 bath sleeps 8 pets ok
Hilton Head Island, SCrated 4.8
Oceanfront Villa, Resort Amenities on Hilton Head, Hilton Head Island, SC from $270

Oceanfront Villa, Resort Amenities on Hilton Head

Oceanfront Condo 3 bed 3 bath sleeps 8
Hilton Head Island, SCrated 4.8
Lagoon Front Oasis with Private Dock and Pool - Beautiful Tranquil Escape, Hilton Head Island, SC from $590

Lagoon Front Oasis with Private Dock and Pool - Beautiful Tranquil Escape

Bayfront House 4 bed 4 bath sleeps 12
Hilton Head Island, SCrated 4.8
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.

All beach stays →

Affiliate disclosure: Sleep By The Beach earns a commission when you book through Whimstay, Vrbo or Booking.com links on this page, at no extra cost to you. Listing details and photos come from the Whimstay feed and belong to the hosts. How we work.

Get new posts in your inbox. No spam, unsubscribe anytime.