Always updated coastal decor
Oceanfront heated pool just steps from the beach
Private beach access through the dunes
True oceanfront location at The Breakers 307
Relaxing space to unwind

Oceanfront & Across from Coligny-Walk Everywhere!

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.87(133 reviews)

$688.60 USD total for 3 nights

Oct 27 – 30, 2026

Living area with pullout sofa
Balcony
Balcony
Entrance
Arial view

Beach location in the center of it all!!!

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.77(156 reviews)

$986.25 USD total for 3 nights

Oct 30 – Nov 2, 2026

Your Breakers Retreat - Steps to Sand, Shops & Sunsets
Ocean Views & Elegant Comfort in North Forest Beach
Beach Ready: Towels, Chairs & Cooler Included
Salt + Serenity – Oceanfront Couple’s Villa
Experience the Difference with MyStay Extras

222 Breakers

1 bedroom·1 bath
Hilton Head Island • South Carolina

$764.14 USD total for 3 nights

Oct 31 – Nov 3, 2026

Living Area
Entry
Patio
Main Area
King Bedroom

208 Breakers

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.75(12 reviews)

$649.50 USD total for 3 nights

Nov 22 – 25, 2026

Welcome to MyStay at 311 Breakers!
Front Row Views, No Matter Where You Sit
Where the Ocean Meets Your Morning Coffee
Salt + Serenity – Oceanfront Villa
Your Stay, Upgraded with MyStay

311 Breakers

1 bedroom·1 bath
Hilton Head Island • South Carolina

$824.32 USD total for 3 nights

Oct 27 – 30, 2026

Living Room with Balcony
Private Balcony Overlooking Pool
Community Pool
Community Walkway
Community Walkway

65 Courtside Villa

2 bedrooms·3 baths
Hilton Head Island • South Carolina

$815.89 USD total for 3 nights

Nov 3 – 6, 2026

Bright and Airy Living Room with Balcony Access
Balcony with Partial Pool View
Bright and Airy Living Room with Balcony Access
Aerial View Above Treetops Pool
Treetops Community Tennis

5804 Treetops

2 bedrooms·1 bath
Hilton Head Island • South Carolina

$1,077.15 USD total for 5 nights

Nov 21 – 26, 2026

Welcome to "Our Happy Place"!
Relax in our sectional or dine al fresco at the dinette table and chairs
Our amazing screened in porch has new patio furniture as of Feb 2021!
The porch is our absolute favorite spot to hang out and relax
Enjoy the Queen sized sleeper sofa and love seat while relaxing

Our Happy Place

3 bedrooms·3 baths
Hilton Head Island • South Carolina
4.98(62 reviews)

$1,438.02 USD total for 3 nights

Oct 27 – 30, 2026

beautiful pool
king bed
Gorgeous kitchen
queen sleeper sofa
gorgeous stand up shower

Chic Beachside Escape at Xanadu Villas

2 bedrooms·1 bath
Hilton Head Island • South Carolina
5(32 reviews)

$695.20 USD total for 3 nights

Oct 27 – 30, 2026

Gorgeous Views of Ocean
We aim to have beach gear ready for you, but please note it's shared and may change between stays.
Queen size bed in primary bedroom
Queen size bed in primary bedroom
Beds in the hall are perfect for young travelers

Oceanfront Oasis: Beachfront Bliss

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.65(86 reviews)

$947.00 USD total for 3 nights

Oct 27 – 30, 2026

Family Room
Family Room
Gourmet Kitchen
Master Bedroom - 2nd Floor King Bed
1st Floor Bedroom Queen

Ocean Breeze 45

3 bedrooms·3 baths
Hilton Head Island • South Carolina

$825.00 USD total for 3 nights

Nov 21 – 24, 2026

Steps to Beach, Sleeps 9, Near Coligny, 2 Kings & Bunk Room, 3 beds. 2.5 baths
Private kitchen
Room
Room
Room

Steps to Beach, Sleeps 9, Near Coligny, 2 Kings & Bunk Room, 3 beds. 2.5 baths

3 bedrooms·2 baths
Hilton Head Island • South Carolina
5(8 reviews)

$930.00 USD $837.75 USD total for 3 nights

Oct 27 – 30, 2026

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

$1,525.74 USD total for 3 nights

Oct 27 – 30, 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 total for 3 nights

Oct 27 – 30, 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

$1,110.99 USD total for 3 nights

Nov 1 – 4, 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 total for 3 nights

Nov 1 – 4, 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 total for 4 nights

Oct 27 – 31, 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 total for 3 nights

Oct 27 – 30, 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

$1,525.74 USD total for 3 nights

Oct 27 – 30, 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)

$707.50 USD total for 4 nights

Nov 1 – 5, 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 total for 3 nights

Oct 27 – 30, 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)

$707.50 USD total for 4 nights

Nov 6 – 10, 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 total for 3 nights

Apr 1 – 4, 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 total for 3 nights

Oct 27 – 30, 2026