Location

Dates

Guests

Vacation rentals in Hilton Head Island, South Carolina, United States

Small density complex with 2 assigned parking spots right across from beach!

Fully equipped kitchen with table for 2

Granite countertops

Light and bright living area with neutral furniture

Spacious King Master with Roku TV

Steel City Escape - Ocean Gate next to Sea Pines

2 bedrooms·2½ baths

Hilton Head Island • South Carolina

5(50 reviews)

$1,054.50 USD total for 3 nights

Oct 3 – 6, 2026

⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐

⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐

⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐

⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐

⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐

⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.91(223 reviews)

$708.75 USD total for 3 nights

Sep 29 – Oct 2, 2026

Ocean views, morning to sunset

Relax, recharge, repeat

Heated pool, year-round vibes

Front-row seat to the Atlantic

Heated pool, year-round vibes

408 Ocean Dunes

1 bedroom·1 bath

Hilton Head Island • South Carolina

$834.36 USD total for 3 nights

Oct 23 – 26, 2026

Living Room/Dining

Living Room/Dining

Living Room/Dining/Kitchen

309 Ocean Dunes Villas

2 bedrooms·2 baths

Hilton Head Island • South Carolina

4.81(190 reviews)

$2,651.50 USD total for 7 nights

Oct 23 – 30, 2026

Hilton Head Sea Pines Getaway

Hilton Head Sea Pines Getaway

Foyer/entry way

Hilton Head Sea Pines Getaway

Hilton Head Sea Pines Getaway

5 bedrooms·3½ baths

Hilton Head Island • South Carolina

4.85(82 reviews)

$1,813.26 USD total for 3 nights

Sep 29 – Oct 2, 2026

Beach path to ocean

Great Room To Kithchen

Dining to Outside

Pet Friendly Luxury Near Ocean Home

3 bedrooms·2 baths

Hilton Head Island • South Carolina

4.84(56 reviews)

$4,075.00 USD total for 7 nights

Sep 29 – Oct 6, 2026

Sea Pines · Walk to Beach · Lagoon Deck · 3BR image 1

Sea Pines · Walk to Beach · Lagoon Deck · 3BR image 3

Sea Pines · Walk to Beach · Lagoon Deck · 3BR image 4

Sea Pines · Walk to Beach · Lagoon Deck · 3BR

Sea Pines · Walk to Beach · Lagoon Deck · 3BR

Sea Pines · Walk to Beach · Lagoon Deck · 3BR

3 bedrooms·2 baths

Hilton Head Island • South Carolina

5(7 reviews)

$1,090.00 USD total for 3 nights

Oct 5 – 8, 2026

Welcome to our bright and open home.

Coastal Chic at Inland Harbour

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(95 reviews)

$2,930.28 USD $2,796.63 USD total for 7 nights

Oct 6 – 13, 2026

Spacious first floor living and dining with sliding door to the deck

54" wall mounted TV, ceiling fan and layered lighting for evening wind down time.

Open floor plan for a great flow and great vacation. Island Song Villa will feel like your own personal villa.

The dining table easily seats 6 for meals.

View from the bottom of the stairs to the dining, kitchen, front door and 1st floor bedroom.

Island Song Villa

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(121 reviews)

$220 – $390/ night(excl. fees & taxes)

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

2 bedrooms·2½ baths

Hilton Head Island • South Carolina

4.98(103 reviews)

$3,445.00 USD total for 3 nights

Oct 11 – 14, 2026

Newly Updated, Near Harbour Town 1st Floor 2 Bedroom 2Bath Villa

2 bedrooms·2 baths

Hilton Head Island • South Carolina

4.7(66 reviews)

$1,221.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access

Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access

Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access

Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access

Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access

Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access

3 bedrooms·3 baths

Hilton Head Island • South Carolina

4.95(81 reviews)

$3,465.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

Amazing view of Harbour Town Links Course

Front of house. Driveway fits 6 cars

Hilton Head Island - Sea Pines House off Harbour Town Golf Links

Hilton Head Island - Sea Pines House off Harbour Town Golf Links

4 bikes included

Hilton Head Island - Sea Pines House off Harbour Town Golf Links

3 bedrooms·3 baths

Hilton Head Island • South Carolina

5(36 reviews)

Bright and cozy living room designed for comfort and relaxation.

Modern and fully equipped kitchen for all your cooking needs

Scenic gazebo offering stunning river views and a tranquil escape.

Bedroom 1 - Bright and relaxing room designed for comfort

The Nest

3 bedrooms·3 baths

Bluffton • South Carolina

$1,273.87 USD total for 3 nights

Oct 4 – 7, 2026

A look at one of our multiple 5 star reviews

Driftwood Inn

4 bedrooms·4½ baths

Bluffton • South Carolina

$1,091.35 USD total for 3 nights

Oct 4 – 7, 2026

SEA PINES 4 Bed + Loft

SEA PINES 4 Bed + Loft

SEA PINES 4 Bed + Loft

SEA PINES 4 Bed + Loft

SEA PINES 4 Bed + Loft

SEA PINES 4 Bed + Loft

4 bedrooms·4 baths

Hilton Head Island • South Carolina

4.9(188 reviews)

$2,331.00 USD total for 4 nights

Oct 7 – 11, 2026

Yay, you're here! Welcome to The Coral Door!

Plenty of room to relax on the front porch - one of 3 large outdoor and covered spaces at The Coral Door!

Living room has seating for 5 plus 2 poufs for extra seating

The Coral Door

3 bedrooms·2½ baths

Bluffton • South Carolina

Kitchen view into living area

Hilton Head Lagoon Paradise in Deer Run

5 bedrooms·5 baths

Hilton Head Island • South Carolina

5(4 reviews)

$2,142.86 USD total for 3 nights

Jun 2 – 5, 2027

Tranquility By The Beach: 12th Row From the Water image 1

Tranquility By The Beach: 12th Row From the Water image 2

Take a dip in the evening

Tranquility By The Beach: 12th Row From the Water image 4

The dining table can accommodate the entire family

Tranquility By The Beach: 12th Row From the Water

5 bedrooms·3½ baths

Hilton Head Island • South Carolina

4.93(59 reviews)

$6,721.50 USD total for 7 nights

Oct 27 – Nov 3, 2026

Sunset view at our beach

Looking into the living room from the dining room.

Living room looking to kitchen/dining and outdoor patio

Master bedroom with king size bed. Master bath to the right of the bed

Sea Pines at South Beach

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(1 review)

$943.50 USD total for 3 nights

Dec 1 – 4, 2026

The Salty Villa

3 bedrooms·2 baths

Hilton Head Island • South Carolina

4.93(148 reviews)

$1,087.50 USD total for 3 nights

Sep 29 – Oct 2, 2026

Private kitchen

Private kitchen

Legacy Island - 110 Acres in Private Island in South Carolina

4 bedrooms·4½ baths

Port Royal • South Carolina

$7,118.41 USD total for 3 nights

Sep 29 – Oct 2, 2026

Sleeps 12! 5 BDRM-2 Kings,3 Queens-Deck & Patio-Mins to PI & Beaufort

Sleeps 12! 5 BDRM-2 Kings,3 Queens-Deck & Patio-Mins to PI & Beaufort

Horseshoe pit in the back yard.

Sleeps 12! 5 BDRM-2 Kings,3 Queens-Deck & Patio-Mins to PI & Beaufort

Sleeps 12! 5 BDRM-2 Kings,3 Queens-Deck & Patio-Mins to PI & Beaufort

Sleeps 12! 5 BDRM-2 Kings,3 Queens-Deck & Patio-Mins to PI & Beaufort

5 bedrooms·2 baths

Port Royal • South Carolina

5(49 reviews)

$807.23 USD total for 3 nights

Oct 3 – 6, 2026

Welcome to 426 Meritta Ave

Welcoming front porch

Sit a spell and swing

Side entrance to screened porch

Bungalow by the Bay in Beautiful Beaufort SC

3 bedrooms·2 baths

Beaufort • South Carolina

5(46 reviews)

$812.50 USD total for 3 nights

Nov 18 – 21, 2026