A completely reimagined coastal retreat made for effortless luxury
Sunrise coffees, ocean breezes, and endless blue views
Your private outdoor lounge above the shoreline
Shorewood Beachfront Community
Resort-Style Zero-Entry Pool, Kiddie Splash Zone & Soothing Hot Tub

334 Shorewood

3 bedrooms·3 baths
Hilton Head Island • South Carolina

$ 1.970,73 USD totaal voor 3 nachten

22–25 okt 2026

Welcome to MyStay at 531 Shorewood
Sun-Filled Living Room with Ocean Views
Your Ocean View Retreat
Shorewood Beachfront Community
Resort-Style Zero-Entry Pool, Kiddie Splash Zone & Soothing Hot Tub

531 Shorewood

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$ 1.317,83 USD totaal voor 3 nachten

29 sep – 2 okt 2026

Balcony Views of the Pool and Ocean!
Balcony Views of the Pool and Ocean!
Primary King Suite with Pool and Ocean Views and Access to Balcony
136 Shorewood
Living Area and Balcony

136 Shorewood

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$ 1.191,22 USD totaal voor 3 nachten

29 sep – 2 okt 2026

100% remodeled
Queen bed pull out.
Bunk beds for the kids!
Updated bathroom
Queen bed in the master

3rd Floor 100% Remodeled Condo- Ocean Views

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.89(109 reviews)

$ 503,00 USD totaal voor 3 nachten

12–15 okt 2026

Beachy Keen Seaside Villa Near Coligny W/Bikes!
Beachy Keen Seaside Villa Near Coligny W/Bikes!
Beachy Keen Seaside Villa Near Coligny W/Bikes!
Beachy Keen Seaside Villa Near Coligny W/Bikes!
Beachy Keen Seaside Villa Near Coligny W/Bikes!

Beachy Keen Seaside Villa Near Coligny W/Bikes!

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.89(111 reviews)

$ 927,50 USD totaal voor 4 nachten

29 sep – 3 okt 2026

The Cockleshell
The Cockleshell
The Cockleshell
The Cockleshell
The Cockleshell

The Cockleshell

3 bedrooms·2½ baths
Hilton Head Island • South Carolina
5(1 review)

$ 736,00 USD totaal voor 3 nachten

7–10 okt 2026

Private Balcony with Uninterrupted Ocean & Pool Views
Sweeping Sunset Views from Your Private Balcony
Bright + Breezy Living Room with Pool Views & Direct Oceanfront Balcony
Private Balcony with Uninterrupted Ocean & Pool Views
Spacious Primary Suite with Plush Bedding & Peaceful Vibes

301 Shorewood

3 bedrooms·3 baths
Hilton Head Island • South Carolina

$ 1.614,74 USD totaal voor 3 nachten

27–30 okt 2026

Seas the Day! Beach & Sun, with Bikes & Chairs
Seas the Day! Beach & Sun, with Bikes & Chairs
Seas the Day! Beach & Sun, with Bikes & Chairs
Seas the Day! Beach & Sun, with Bikes & Chairs
Seas the Day! Beach & Sun, with Bikes & Chairs

Seas the Day! Beach & Sun, with Bikes & Chairs

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.84(68 reviews)

$ 945,10 USD totaal voor 4 nachten

10–14 okt 2026

Wake Up to Sweeping Pool Views from Your Private Balcony
Rare 3rd-Floor Balcony with Sweeping Pool Views
Wake Up to Sweeping Pool Views from Your Private Balcony
Open Living Space with Relaxed Coastal Vibes
Just Steps to the Pool, Minutes to the Beach

3070 Seascape

3 bedrooms·2 baths
Hilton Head Island • South Carolina

$ 867,64 USD totaal voor 3 nachten

29 sep – 2 okt 2026

Brand new gorgeous shower
SunnyDaze-Brand new reno- King bed, Free bikes! image 2
Lots of cabinet space
New cabinets and appliances
Queen sleeper sofa

SunnyDaze-Steps to the Ocean king bed, Free bikes!

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.69(179 reviews)

$ 901,10 USD totaal voor 4 nachten

5–9 okt 2026

Overview
Entrance
Entrance
Living/Dining Area
Livingroom with pullout sofa

Make Seascape your Escape!

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.89(36 reviews)

$ 769,80 USD totaal voor 3 nachten

1–4 apr 2027

Beautiful view of the ocean from the balcony!
OceanEscape – Steps to the Beach image 2
Queen bed
Queen sleeper sofa
Tub/shower combo

OceanEscape – Steps to the Beach

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.86(90 reviews)

$ 662,20 USD totaal voor 3 nachten

19–22 okt 2026

Salty Shores! -Incredible ocean views
Salty Shores! -Incredible ocean views
Salty Shores! -Incredible ocean views
Salty Shores! -Incredible ocean views
Salty Shores! -Incredible ocean views

Salty Shores! -Incredible ocean views

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.67(231 reviews)

$ 1.015,50 USD totaal voor 4 nachten

8–12 okt 2026

Castaways King Villa on Beach, Free Bikes!
Castaways King Villa on Beach, Free Bikes!
Castaways King Villa on Beach, Free Bikes!
Castaways King Villa on Beach, Free Bikes!
Castaways King Villa on Beach, Free Bikes!

Castaways King Villa on Beach, Free Bikes!

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(148 reviews)

$ 677,20 USD totaal voor 3 nachten

3–6 okt 2026

Elegance at the beach -Ocean View Villa, Gorgeous!
Elegance at the beach -Ocean View Villa, Gorgeous!
Elegance at the beach -Ocean View Villa, Gorgeous!
Elegance at the beach -Ocean View Villa, Gorgeous!
Elegance at the beach -Ocean View Villa, Gorgeous!

Elegance at the beach -Ocean View Villa, Gorgeous!

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.87(275 reviews)

$ 901,10 USD totaal voor 4 nachten

23–27 okt 2026

Good Times and Tan Lines!-Central air, free bikes!
Good Times and Tan Lines!-Central air, free bikes!
Good Times and Tan Lines!-Central air, free bikes!
Good Times and Tan Lines!-Central air, free bikes!
Good Times and Tan Lines!-Central air, free bikes!

Good Times and Tan Lines!-Central air, free bikes!

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.84(153 reviews)

$ 901,10 USD totaal voor 4 nachten

29 sep – 3 okt 2026

Feelin Tip'Sea-Oceanview Retreat Steps to Beach
Feelin Tip'Sea-Oceanview Retreat Steps to Beach
Feelin Tip'Sea-Oceanview Retreat Steps to Beach
Feelin Tip'Sea-Oceanview Retreat Steps to Beach
Feelin Tip'Sea-Oceanview Retreat Steps to Beach

Feelin Tip'Sea-Oceanview Retreat Steps to Beach

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.8(85 reviews)

$ 927,50 USD totaal voor 4 nachten

4–8 okt 2026

BEach Happy HHI, Steps to the Beach
BEach Happy HHI, Steps to the Beach
BEach Happy HHI, Steps to the Beach
BEach Happy HHI, Steps to the Beach
BEach Happy HHI, Steps to the Beach

BEach Happy HHI, Steps to the Beach

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.91(95 reviews)

$ 621,60 USD totaal voor 3 nachten

1–4 okt 2026

The fan/light in the bedroom has 3 speeds and the LED light can change to any color!
The unit is located just steps from the beach!
3 barstools at the dining/workspace. The TVs are both 50 inch Samsung. Cable is provided and you can stream Netflix and YouTube from the cable box.
Community Pool
View from balcony

Best location on HHI! Oceanfront + Walkable

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(47 reviews)

$ 837,80 USD totaal voor 3 nachten

8–11 okt 2026

Stay Seaside
Stay Seaside
Stay Seaside
Queen Sleeper Sofa
Stay Seaside

Stay Seaside

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(108 reviews)

$ 957,50 USD totaal voor 3 nachten

29 sep – 2 okt 2026

View of the ocean from the balcony
King bed
Queen sleeper sofa
Pool in the evening
Wide beach

Pelican Roost at Seaside Steps to the Beach

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.88(24 reviews)

$ 715,00 USD totaal voor 3 nachten

18–21 okt 2026

SHOREthing! Beachside retreat w/ Bikes, Chairs
SHOREthing! Beachside retreat w/ Bikes, Chairs
SHOREthing! Beachside retreat w/ Bikes, Chairs
SHOREthing! Beachside retreat w/ Bikes, Chairs
SHOREthing! Beachside retreat w/ Bikes, Chairs

SHOREthing! Beachside retreat w/ Bikes, Chairs

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.78(275 reviews)

$ 927,50 USD totaal voor 4 nachten

3–7 okt 2026

Seaside 2 pool
everything need to cook meals
Queen bed
Gorgeous stand up shower
Coastal Blue – Oceanview Condo in the Heart of Hil image 5

Coastal Blue – Oceanview Condo in the Heart of Hil

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.88(24 reviews)

$ 728,20 USD totaal voor 3 nachten

30 sep – 3 okt 2026

Unmatched views of the ocean and beach. This location on the island can not be beat.
Perfect cozy spot to relax at night and take in the ocean breeze.
Wavefront Bliss: Your Hilton Head Coastal Escape
Perfect sunset views!
Wavefront Bliss: Your Hilton Head Coastal Escape

Wavefront Bliss: Your Hilton Head Coastal Escape

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.83(30 reviews)

$ 733,00 USD totaal voor 3 nachten

20–23 okt 2026