Sleeps 8+ stays in Hilton Head Island

114 sleeps eight or more rentals around 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 114, 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
Private Dock and Hot Tub with Lake View - Charming Tranquil Retreat, Talahi Island, GA from $165

Private Dock and Hot Tub with Lake View - Charming Tranquil Retreat

Canal front House 3 bed 3 bath sleeps 8 pets ok
Talahi Island, GArated 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
Compare before you book

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

Search Vrbo → Booking.com → Affiliate links.
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
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
Exclusive Pool and Five Unique Apartments - Stunning Beachside Villa, Tybee Island, GA from $1,214

Exclusive Pool and Five Unique Apartments - Stunning Beachside Villa

Beachfront Villa 9 bed 8 bath sleeps 28
Tybee Island, GArated 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
Unique Dock House and Scenic Water Views - Stunning Waterfront Estate, Okatie, SC from $1,932

Unique Dock House and Scenic Water Views - Stunning Waterfront Estate

Waterfront Apartment 5 bed 5.5 bath sleeps 28
Okatie, 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
High Speed Wi-Fi and Two-Person Jacuzzi Tub - Charming Lake Home, Wilmington Island, GA from $153

High Speed Wi-Fi and Two-Person Jacuzzi Tub - Charming Lake Home

Waterfront Vacation Rental 4 bed 2 bath sleeps 10 pets ok
Wilmington Island, GArated 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
Private Dock and Bubbling Hot Tub - Charming Idyllic Retreat, Talahi Island, GA from $213

Private Dock and Bubbling Hot Tub - Charming Idyllic Retreat

Canal front House 4 bed 4 bath sleeps 10 pets ok
Talahi Island, GArated 4.9
Exclusive Heated Pool and Spacious Living - Luxurious Coastal Haven, Tybee Island, GA from $423

Exclusive Heated Pool and Spacious Living - Luxurious Coastal Haven

Oceanfront House 4 bed 2 bath sleeps 12
Tybee Island, GArated 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
Unique Retreat with Outdoor Adventures - Exquisite Private Island, Port Royal, SC from $1,449

Unique Retreat with Outdoor Adventures - Exquisite Private Island

Canal front House 4 bed 4.5 bath sleeps 15
Port Royal, 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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