Location

Dates

Guests

Vacation rentals in Hilton Head Island, South Carolina, United States

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 22 – 25, 2026

Living area with pullout sofa

Beach location in the center of it all!!!

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.77(156 reviews)

$930.75 USD total for 3 nights

Sep 29 – Oct 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

$833.09 USD total for 3 nights

Sep 29 – Oct 2, 2026

208 Breakers

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.75(12 reviews)

$150/ night(excl. fees & taxes)

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 25 – 28, 2026

Living Room with Balcony

Private Balcony Overlooking Pool

Community Walkway

Community Walkway

65 Courtside Villa

2 bedrooms·3 baths

Hilton Head Island • South Carolina

$815.89 USD total for 3 nights

Sep 29 – Oct 2, 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

Sep 29 – Oct 2, 2026

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 5 – 8, 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

Sep 29 – Oct 2, 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

$1,970.73 USD total for 3 nights

Oct 22 – 25, 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

Sep 29 – Oct 2, 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

Living Area and Balcony

136 Shorewood

2 bedrooms·2 baths

Hilton Head Island • South Carolina

$1,191.22 USD total for 3 nights

Sep 29 – Oct 2, 2026

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

Oct 12 – 15, 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

Sep 29 – Oct 3, 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 7 – 10, 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 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)

$945.10 USD total for 4 nights

Oct 10 – 14, 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

Sep 29 – Oct 2, 2026

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 total for 4 nights

Oct 5 – 9, 2026

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 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 19 – 22, 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 total for 4 nights

Oct 8 – 12, 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 total for 3 nights

Oct 3 – 6, 2026