2 bedroom 2 bath 4 min drive to beach
2 bedroom 2 bath 4 min drive to beach
2 bedroom 2 bath 4 min drive to beach
2 bedroom 2 bath 4 min drive to beach
2 bedroom 2 bath 4 min drive to beach

2 bedroom 2 bath 4 min drive to beach

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$2,950.00 USD total for 30 nights

Oct 20 – Nov 19, 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 20 – 27, 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 20 – 23, 2026

BEST Location on the island just steps to the sand
Entryway
BEST Location on the island just steps to the sand
BEST Location on the island just steps to the sand
BEST Location on the island just steps to the sand

BEST Location on the island just steps to the sand

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

$1,330.00 USD total for 3 nights

Oct 20 – 23, 2026

Pool and looking up to Villa
Private cabanas for rent @ Westin
Port Royal Golf & Racquet Club Pro Shop
Great Room
Fire pits @ Westin

Ocean Palms w/ Westin access

3 bedrooms·3 baths
Hilton Head Island • South Carolina

$2,271.00 USD total for 6 nights

Oct 20 – 26, 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

$1,770.00 USD total for 5 nights

Oct 24 – 29, 2026

Entrance
Office Space in Entry Way
3rd full bathroom with washer and dryer
3rd Full bath with washer/dryer
Living room and dining area

The Moorings - Dunes House View

2 bedrooms·3 baths
Hilton Head Island • South Carolina
5(1 review)

$1,165.00 USD $1,066.00 USD total for 3 nights

Oct 20 – 23, 2026

One of kind 3 bedroom Villa with Ocean/Lagoon View
One of kind 3 bedroom Villa with Ocean/Lagoon View
One of kind 3 bedroom Villa with Ocean/Lagoon View
One of kind 3 bedroom Villa with Ocean/Lagoon View
One of kind 3 bedroom Villa with Ocean/Lagoon View

One of kind 3 bedroom Villa with Ocean/Lagoon View

3 bedrooms·2 baths
Hilton Head Island • South Carolina
4.98(40 reviews)

$1,451.25 USD total for 5 nights

Oct 20 – 25, 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

Beautiful view from the balcony off the living room and master bedroom
3 oceanfront balconies directly on the beach
Beautiful sunrise photo taken from the balcony off the living room and master.
Large balcony over the ocean with dining for 6
Unobstructed views

3233 Villamare

3 bedrooms·3 baths
Hilton Head Island • South Carolina
4.96(83 reviews)

$3,330.00 USD total for 7 nights

Oct 24 – 31, 2026

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)

$1,359.75 USD total for 3 nights

Oct 20 – 23, 2026

Peaceful first floor Villa with wildlife view
Peaceful first floor Villa with wildlife view
Peaceful first floor Villa with wildlife view
Peaceful first floor Villa with wildlife view
Peaceful first floor Villa with wildlife view

Peaceful first floor Villa with wildlife view

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.88(52 reviews)

$843.60 USD total for 3 nights

Nov 7 – 10, 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

Oct 20 – 27, 2026

Front of our home
Quiet Hilton Head house on Shipyard golf, by beach image 23
Quiet Hilton Head house on Shipyard golf, by beach image 28
All season patio, everyone's favorite spot!
Quiet Hilton Head house on Shipyard golf, by beach image 3

Quiet Hilton Head house on Shipyard golf,by beach

3 bedrooms·2 baths
Hilton Head Island • South Carolina
4.86(58 reviews)

$987.90 USD total for 3 nights

Oct 25 – 28, 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
4.95(137 reviews)

$1,974.50 USD $1,826.00 USD total for 7 nights

Nov 6 – 13, 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)

$1,523.50 USD total for 5 nights

Feb 8 – 13, 2027

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

$3,225.00 USD total for 7 nights

Nov 8 – 15, 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

2BR/2.5BA|Direct Oceanfront Resort|Guest Favorite

2 bedrooms·2½ baths
Hilton Head Island • South Carolina
4.99(80 reviews)

$912.49 USD total for 3 nights

Dec 1 – 4, 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 25 – 29, 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 26 – Nov 2, 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

$1,594.99 USD total for 3 nights

Oct 23 – 26, 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)

$1,435.50 USD total for 7 nights

Oct 20 – 27, 2026

3424 Direct Ocean/Pool Views 2BR/2BA/Fitness/Pools image 1
3424 Direct Ocean/Pool Views 2BR/2BA/Fitness/Pools image 2
3424 Direct Ocean/Pool Views 2BR/2BA/Fitness/Pools image 3
3424 Direct Ocean/Pool Views 2BR/2BA/Fitness/Pools image 4
View from the master bedroom balcony.

3424 Direct Ocean/Pool Views 2BR/2BA/Fitness/Pools

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(50 reviews)

$1,578.50 USD total for 3 nights

Oct 24 – 27, 2026