Big Ocean & Pool Views from private 3rd floor balcony!
KING BED & 65" HD SmartTV with free Netflix & Amazon Prime! Rare enlarged bedroom!
100% New renovation by HGTV featured designer!
All new fully-stocked designer kitchen with full-size stainless appliances & marble backsplash!
Oceanview Designer! KING BED Bar! 65"TV Tennis GYM

Oceanview Designer! KING BED Bar! 65"TV Tennis GYM

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(31 reviews)

$3,221.46 USD total for 7 nights

Oct 17 – 24, 2026

Panoramic Oceanfront Views the moment you open the door! All New Luxury condo designed by an HGTV featured decorator! Stunning unobstructed views of the Ocean, Pool, Coastal Marsh & Dunes!
An HGTV featured decorator just completed a 100% NEW renovation on April 2023 - featuring luxurious Coastal Décor, utilizing a soothing Sand & Sea Color Palette!
Oceanfront Balcony offers views of the Ocean and Beautiful Coastal Marsh with its Windswept Dune Trees!
Sunrise from your Beachfront Balcony!
KING BED in Expanded Bedroom! Highly Rated 12” Memory Foam Mattress. 65" SmartTV w/ FREE Netflix, Prime & Cable TV!

Oceanfront Luxury! KING BED 75"TV Pickleball & BAR

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.93(59 reviews)

$4,076.46 USD total for 7 nights

Sep 29 – Oct 6, 2026

View from private deck
103 Carolina Club Shipyard Planation
View of front of house
View of back of house
Aerial view of amenities

103 Carolina Club Shipyard Planation

3 bedrooms·3 baths
Hilton Head Island • South Carolina

$1,279.00 USD total for 7 nights

Nov 8 – 15, 2026

Carolina Club @ Shipyard
Carolina Club @ Shipyard
Carolina Club @ Shipyard
Bedroom 1
Bath 1

Carolina Club @ Shipyard

3 bedrooms·3 baths
Hilton Head Island • South Carolina

$1,715.00 USD total for 7 nights

Oct 25 – Nov 1, 2026

Beach Skybox HHI - panoramic view
Beach Skybox HHI - panoramic view
Beach Skybox HHI - panoramic view
Beach Skybox HHI - panoramic view
Beach Skybox HHI - panoramic view

Beach Skybox HHI - panoramic view

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(201 reviews)

$924.00 USD total for 3 nights

Oct 4 – 7, 2026

Sea Horse Dream
Sea Horse Dream
Sea Horse Dream
Sea Horse Dream
Sea Horse Dream

Sea Horse Dream

4 bedrooms·3 baths
Hilton Head Island • South Carolina
4.91(32 reviews)

$2,205.00 USD total for 4 nights

Sep 29 – Oct 3, 2026

Welcome to 55 Moorings!
Coastal Comfort - 55 MOORINGS
Coastal Comfort - 55 MOORINGS
Coastal Comfort - 55 MOORINGS
Coastal Comfort - 55 MOORINGS

Coastal Comfort - 55 MOORINGS

2 bedrooms·3 baths
Hilton Head Island • South Carolina

$3,185.00 USD total for 7 nights

Oct 13 – 20, 2026

New backyard pool and putting green
Heels in the Sand
Heels in the Sand
Heels in the Sand
Heels in the Sand

Heels in the Sand

3 bedrooms·2½ baths
Hilton Head Island • South Carolina
4.92(51 reviews)

$1,652.00 USD total for 3 nights

Oct 11 – 14, 2026

View from balcony - pool right out back
Ocean Palms Villas includes DAILY GOLF
Pool and looking up to Villa
Hilton Head Villa with daily golf, tennis & surf
Aerial of villas

Hilton Head Villa with daily golf, tennis & surf

3 bedrooms·3 baths
Hilton Head Island • South Carolina

$1,975.00 USD total for 5 nights

Oct 10 – 15, 2026

Living Room with a view
Living area
Living area
Quiet gated community
Welcome to our home!

Our Happy Place

2 bedrooms·3 baths
Hilton Head Island • South Carolina

$1,887.00 USD total for 4 nights

May 1 – 5, 2027

Living area with work desk
Open concept living area
Ocean-View Palmetto Dunes Condo
Fully stocked kitchen with all major appliances.
Ocean-View Palmetto Dunes Condo

Ocean-View Palmetto Dunes Condo

3 bedrooms·3 baths
Hilton Head Island • South Carolina
4.77(62 reviews)

$1,492.95 USD total for 3 nights

Sep 29 – Oct 2, 2026

Directly on the Beach!
Directly on the Beach!
Directly on the Beach!
Directly on the Beach!
Directly on the Beach!

Directly on the Beach!

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$2,520.00 USD total for 7 nights

Sep 29 – Oct 6, 2026

2519 Villamare
Community Pool 1 of 3 with Children's Area
Primary King Suite with Private Balcony & Coastal Views
Family-Friendly Suite with Ocean Views & Private Balcony
Ocean Views from Your Living & Dining Room

2519 Villamare

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$4,112.09 USD total for 3 nights

Mar 11 – 14, 2027

1405 Villamare in Palmetto Dunes, Hilton Head
1405 Villamare in Palmetto Dunes, Hilton Head
1405 Villamare in Palmetto Dunes, Hilton Head
1405 Villamare in Palmetto Dunes, Hilton Head
1405 Villamare in Palmetto Dunes, Hilton Head

1405 Villamare in Palmetto Dunes, Hilton Head

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(136 reviews)

$1,864.50 USD $1,699.50 USD total for 7 nights

Dec 13 – 20, 2026

Look out over the ocean while relaxing in living room!
1404 Villamare in Palmetto Dunes, Hilton Head
1404 Villamare in Palmetto Dunes, Hilton Head
1404 Villamare in Palmetto Dunes, Hilton Head
1404 Villamare in Palmetto Dunes, Hilton Head

1404 Villamare in Palmetto Dunes, Hilton Head

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.94(204 reviews)

$1,314.50 USD total for 5 nights

Nov 14 – 19, 2026

New Family Pool - Open April 2024
Fully stocked kitchen
New Serenity Pool / Hot Tub - Open 2024
New Family Pool / Hot Tub
Balcony View from 3rd floor.

3327 Villamare 🏝 Hilton Head Island

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$3,820.00 USD total for 7 nights

Sep 29 – Oct 6, 2026

Living room with 2 full size couches (one is a queen sleeper) and oversized plush chair leading to private deck overlooking serene lagoon
Island Club Pool
Island Club community
Large king master with en suite, walk in closet and balcony
Fully stocked and just updated kitchen leading to open first floor

Direct Oceanfront Community - Guest Favorite

2 bedrooms·2½ baths
Hilton Head Island • South Carolina
5(79 reviews)

$1,146.87 USD total for 3 nights

Sep 29 – Oct 2, 2026

Start your day with a beautiful sunrise
Island Club full amenity ocean front resort
Open concept living space. Updated comfortable furniture and dining for 6
Beautiful beach steps away
King bed with new memory foam mattress, very comfortable! Door to patio. Smart TV with remote, USB nightstands. Ocean facing

Direct Ocean Front Nestled in the Dunes

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(40 reviews)

$1,760.00 USD total for 4 nights

Oct 17 – 21, 2026

View off back deck of quiet lagoon
Oceanfront pool complex across the street from the villa
Open living room and sun room
Living room and dining room view with staircase leading to upstairs bedroom
Sun room leading to outdoor deck

Fully Renovated Beach Townhome!

4 bedrooms·3 baths
Hilton Head Island • South Carolina
5(101 reviews)

$6,685.25 USD $6,044.23 USD total for 7 nights

Oct 18 – 25, 2026

Living Room Area
View from Main Balcony of Adults-Only Pool
Primary King Bedroom with Entrance to Balcony and Desk
Birdseye View of Villamare!
Communal Fire Pit

1208 Villamare

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$1,737.88 USD total for 3 nights

Oct 17 – 20, 2026

Welcome to Sweet Beach Villa, 167 Colonnade Club! This first/ground floor unit has been updated and is ready for your vacation to begin!
Our 1,200 SF unit has a great open floorplan which makes socializing a breeze from the kitchen and into the living area!
Our fully equipped kitchen has everything you need to make a meal, or enjoy a coffee while viewing the lagoon and wildlife from our deck!
Our kitchen is equipped with LG stainless steel appliances
Fully equipped Kitchen looking into the dining and living spaces

Sweet Beach Villa, Shipyard Plantation, Ground Flr

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(3 reviews)

$1,551.00 USD total for 7 nights

Sep 29 – Oct 6, 2026

View from the living room swivel chair.
Living Room with new La-Z-Boy sofa & Love Seat
Dining table with 6 chairs
Living Room with new furnishings.
Main Suite with King Bed.

Villamare 3328, 5 stars, Ocean views

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(4 reviews)

$2,280.53 USD $1,878.04 USD total for 7 nights

Oct 3 – 10, 2026

Swimming poor 6-3 feet May heat w/additional charge
“Dune” It Right
In private neighborhood w/ lots of greenery
“Dune” It Right
“Dune” It Right

“Dune” It Right

5 bedrooms·5½ baths
Hilton Head Island • South Carolina
5(100 reviews)

$3,393.00 USD total for 7 nights

Oct 10 – 17, 2026

Family Room
Family Pool and Hot Tub
Serenity Pool and Hot Tub
Master Bedroom
Guest Bedroom

Oceanfront Listing! 3125 Villamare

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(61 reviews)
$460 – $675/ night(excl. fees & taxes)