Dining Area
Living Room
Private Balcony Seating Area
Open Kitchen and Island
Community Pool

95 Forest Gardens

2 bedrooms·2 baths
Hilton Head Island • South Carolina
$110 – $251/ nacht(excl. kosten & belastingen)
Relaxcation!
Relaxcation!
Relaxcation!
Relaxcation!
Relaxcation!

Relaxcation!

2 bedrooms·2½ baths
Hilton Head Island • South Carolina

$ 841,00 USD totaal voor 3 nachten

31 okt – 3 nov 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 totaal voor 3 nachten

21–24 okt 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
$140 – $372/ nacht(excl. kosten & belastingen)
Living room
Bedroom with King bed.
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 totaal voor 3 nachten

26–29 sep 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
$156 – $552/ nacht(excl. kosten & belastingen)
South Forest Beach Villa- 2b/2b- Pet Friendly
South Forest Beach Villa- 2b/2b- Pet Friendly
South Forest Beach Villa- 2b/2b- Pet Friendly
South Forest Beach Villa- 2b/2b- Pet Friendly
South Forest Beach Villa- 2b/2b- Pet Friendly

South Forest Beach Villa- 2b/2b- Pet Friendly

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

$ 800,00 USD totaal voor 3 nachten

25–28 sep 2026

Condo w/ pool - Walk to the beach image 1
Condo w/ pool - Walk to the beach image 2
Condo w/ pool - Walk to the beach image 3
Condo w/ pool - Walk to the beach image 4
Condo w/ pool - Walk to the beach image 5

Condo w/ pool - Walk to the beach

2 bedrooms·1 bath
Hilton Head Island • South Carolina
$160 – $225/ nacht(excl. kosten & belastingen)
Living Room
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)
$117 – $240/ nacht(excl. kosten & belastingen)
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
$124 – $362/ nacht(excl. kosten & belastingen)
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
$299 – $1.369/ nacht(excl. kosten & belastingen)
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 totaal voor 3 nachten

25–28 sep 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
$259 – $852/ nacht(excl. kosten & belastingen)
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
$208 – $613/ nacht(excl. kosten & belastingen)
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
$299 – $1.395/ nacht(excl. kosten & belastingen)
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

25–29 sep 2026

Great room
Great room and dining room
Great room
Dining room
Dining room

Sea Pines Villa with Lagoon Views

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

$ 2.225,85 USD totaal voor 5 nachten

25–30 sep 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 totaal voor 3 nachten

27–30 sep 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 totaal voor 3 nachten

27–30 sep 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

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
$117 – $276/ nacht(excl. kosten & belastingen)
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

27 sep – 1 okt 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)
$150 – $425/ nacht(excl. kosten & belastingen)
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

25–28 sep 2026