Location

Dates

Guests

Vacation rentals in Hilton Head Island

Private Balcony Seating Area

Open Kitchen and Island

95 Forest Gardens

2 bedrooms·2 baths

Hilton Head Island • South Carolina

$753.74 USD total for 3 nights

Sep 27 – 30, 2026

5 minute walk to the beach!

Bright & fresh Coligny gem!

Bright & fresh Coligny gem!

Bright & fresh Coligny gem!

Bright & fresh Coligny gem!

2 bedrooms·2½ baths

Hilton Head Island • South Carolina

5(5 reviews)

$1,251.20 USD $1,200.14 USD total for 4 nights

Sep 22 – 26, 2026

Cozy Living Space with Natural Light & Balcony Views

Relax & Recline: Balcony with Footrest Loungers

Relax & Recline: Balcony with Footrest Loungers

Effortless Nights In: Enjoy a Fully Stocked Home and Smart Entertainment

Primary Suite with Private Balcony

4 Beach Arbor

2 bedrooms·3 baths

Hilton Head Island • South Carolina

$933.74 USD total for 3 nights

Oct 3 – 6, 2026

Breakers 220 ocean View Coligny Beach Hilton Head

Private kitchen

Breakers 220 Oceanfront Condo – Direct Beach Access & Elevator

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.9(59 reviews)

$920.03 USD total for 3 nights

Sep 27 – 30, 2026

Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access

Breakers 324 Hilton Head Ocean view from Balcony

Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access

Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access

Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access

Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access

1 bedroom·1 bath

Hilton Head Island • South Carolina

$708.82 USD total for 3 nights

Oct 27 – 30, 2026

Breakers 328 Collage

Building Breakers 328 Hilton Head SC

living room with Ocean View

Bedroom with Built ins and reading lights at head of Bed w USB chargers, roku smart tv

Breakers 328 Oceanfront Hilton Head Condo Direct Beach Access

1 bedroom·1 bath

Hilton Head Island • South Carolina

5(2 reviews)

$920.03 USD total for 3 nights

Sep 27 – 30, 2026

Living Room with Courtyard View

Main Balcony with View of Ocean and Water Gardens

Pool Bar Jim's Outdoor Beach Bar and Restaurant by Pools

1 of 2 Oceanfront Pools with Kiddie Pool

1102 SeaCrest

2 bedrooms·2 baths

Hilton Head Island • South Carolina

$1,362.95 USD total for 3 nights

Oct 2 – 5, 2026

Living Area with Balcony

Balcony with Tennis Court View

Dining Area and Kitchen

Aerial View of Forest Beach Villas

Aerial View of Forest Beach Villas

307 Forest Beach Villa

1 bedroom·1 bath

Hilton Head Island • South Carolina

$805.51 USD total for 3 nights

Sep 27 – 30, 2026

Lagoon Lookout: Morning Coffee, Sunset Magic

Coastal Living Area: Relax, Recharge, Repeat

Coastal Living Room: Kick Back with Cable & Streaming

SeaCrest's Private Beach Path

Pool Bar Jim's Outdoor Beach Bar and Restaurant by Pools

1105 SeaCrest

2 bedrooms·2 baths

Hilton Head Island • South Carolina

$1,582.31 USD total for 4 nights

Sep 26 – 30, 2026

Freshly Renovated Retreat Steps from the Beach

The South Forest Beach Stay You’ve Been Looking For

Your Primary Balcony - Wake Up in the Heart of South Forest Beach

Aerial View of Forest Beach Villas

Aerial View of Forest Beach Villas

308 Forest Beach Villa

1 bedroom·1 bath

Hilton Head Island • South Carolina

$801.76 USD total for 3 nights

Sep 27 – 30, 2026

Welcome to the SeaCrest Oceanfront Resort

Oceanview Pool + Kiddie Pool Fun

Bright and Coastal Living Space with Ocean Views

Your Home Base for Meals & Memories

Pool Bar Jim's Bar & Restaurant - Your Poolside Cocktail Stop

2313 SeaCrest

2 bedrooms·2 baths

Hilton Head Island • South Carolina

$1,207.51 USD total for 3 nights

Sep 28 – Oct 1, 2026

Aerial View Above Treetops Pool

Treetops Community Tennis

Community Sun Deck by Pool

Patio & Outdoor Dining

6401 Treetops

2 bedrooms·3 baths

Hilton Head Island • South Carolina

4.33(3 reviews)

$785.82 USD total for 3 nights

Oct 30 – Nov 2, 2026

Bedroom with King bed.

Bedroom with king bed

Large shower-no bench

Couples Retreat

1 bedroom·1 bath

Hilton Head Island • South Carolina

5(29 reviews)

$769.50 USD $589.66 USD total for 3 nights

Sep 26 – 29, 2026

Forest Beach Villas – Prime Location Near Iconic Coligny Beach

Laid-Back Living – Relax in a Bright, Beachy Gathering Space

Breathe in the Beach Breeze – Private Balcony with Peaceful Views

Game, Set, Splash – Aerial Perspective on Tennis and Poolside Fun

Sparkling Pool – Dive Into Relaxation Steps From Your Door

223 Forest Beach Villa

3 bedrooms·2 baths

Hilton Head Island • South Carolina

$1,059.60 USD total for 3 nights

Sep 22 – 25, 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

$838.11 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)

$649.50 USD total for 3 nights

Oct 21 – 24, 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

$825.57 USD total for 3 nights

Oct 4 – 7, 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

$812.14 USD total for 3 nights

Sep 28 – Oct 1, 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

$1,070.88 USD total for 5 nights

Nov 21 – 26, 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

$1,955.69 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 28 – Oct 1, 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

$1,144.85 USD total for 3 nights

Sep 27 – 30, 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)

$392.00 USD total for 3 nights

Sep 22 – 25, 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)

$685.00 USD total for 3 nights

Sep 27 – 30, 2026