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)

$750.93 USD total for 3 nights

Sep 27 – 30, 2026

Living Room
Living Room
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

Front of home
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 23 – 26, 2026

Bayberry Breeze - Steps to the Shore - Pool/Hottub
Bayberry Breeze - Steps to the Shore - Pool/Hottub
Main living area
Bayberry Breeze - Steps to the Shore - Pool/Hottub
Bayberry Breeze - Steps to the Shore - Pool/Hottub

Bayberry Breeze - Steps to the Shore - Pool/Hottub

5 bedrooms·4 baths
Hilton Head Island • South Carolina
$382 – $2,193/ night(excl. fees & taxes)
Beach path to ocean
Great Room To Kithchen
Walk to beach
Outside area
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 23 – 30, 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)
$325 – $450/ night(excl. fees & taxes)
Living room
Welcome!
Welcome to our bright and open home.
Foyer
Living room

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

Sep 23 – 30, 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

Dining
Dining
Dining
Dining
Living area

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 23 – 26, 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)
Fall Golf and Cozy Villa equals Perfect Escape! image 1
Cover
Fall Golf and Cozy Villa equals Perfect Escape! image 3
Fall Golf and Cozy Villa equals Perfect Escape! image 4
Fall Golf and Cozy Villa equals Perfect Escape! image 5

Spring and summer dates available!

1 bedroom·1 bath
Beaufort County • South Carolina
4.87(23 reviews)

$753.50 USD total for 3 nights

Sep 26 – 29, 2026

Bright and cozy living room designed for comfort and relaxation.
Modern and fully equipped kitchen for all your cooking needs
The Nest
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

$1,027.95 USD total for 3 nights

Sep 27 – 30, 2026

Bluffton Carriage House
On the River in Bluffton. Your less than two blocks from Oyster Factory Park
The Carriage House
Outside view of the Carriage House
Kitchen/Living Room

The Carriage House

1 bedroom·1 bath
Bluffton • South Carolina

$847.27 USD total for 3 nights

Sep 25 – 28, 2026

The BOHO
Your BackYard Oasis
Chef Worthy Kitchen fully Equipped
Back of the BOHO With Patio and Grill
Walk to Everything Promenade

Bluffton BOHO

4 bedrooms·3 baths
Bluffton • South Carolina

$984.48 USD total for 3 nights

Oct 4 – 7, 2026

Entire Property is Yours
Close to the May River
The BOHO HA
The BOHO
The Carriage House

The BOHO HA

5 bedrooms·4 baths
Bluffton • South Carolina

$1,124.88 USD total for 3 nights

Oct 5 – 8, 2026

Driftwood Inn
Driftwood Inn
A look at one of our multiple 5 star reviews
Driftwood Inn
Driftwood Inn

Driftwood Inn

4 bedrooms·4½ baths
Bluffton • South Carolina

$1,016.83 USD total for 3 nights

Sep 27 – 30, 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)

$3,330.00 USD total for 4 nights

Sep 27 – Oct 1, 2026

The Coral Door
Yay, you're here! Welcome to The Coral Door!
Enjoy the INCLUDED brand new electric golf cart for rides to the Corner Perk for coffee, old town Bluffton, or to the pier in the evenings. Golf carts are a big part of life in Bluffton!
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
Aerial view
Front of home
Entryway
Entryway
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
Large kitchen
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

Kitchen
Kitchen
Kitchen
Kitchen
Dining Room

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 26 – 29, 2026