Location

Dates

Guests

Vacation rentals in Hilton Head Island

Patio with Golf Course Views

Double Full Suite Balcony

Golfmaster Community Pool

Shipyard Beach Club Beach Path

1302 Golfmaster

3 bedrooms·3 baths

Hilton Head Island • South Carolina

$1,016.74 USD total for 3 nights

Sep 22 – 25, 2026

Lagoon Luxe at Barrington Park – Private Beach, Pool & Balcony Bliss

Binge, Relax, Repeat – Living Room with Streaming & Lagoon Views

Relax, Recharge & Unwind – Elegant Lagoon Retreat Near the Beach

Relax, Recharge & Unwind – Elegant Lagoon Retreat Near the Beach

Palmetto Dunes Perfection – Pool, Hot Tub & Private Beach Access

702 Barrington Park

3 bedrooms·3 baths

Hilton Head Island • South Carolina

$1,558.47 USD total for 3 nights

Sep 25 – 28, 2026

Private Resort-Style Pool & Sun Deck

Inviting Living Space for Entertainment & Relaxation

Bright Dining Room with Seating for Everyone

The Ultimate Kids’ Quarters – Bunks, Loft & Movie Zone

Bright Kitchen with Ample Counter Space

7 Salem Road

4 bedrooms·4 baths

Hilton Head Island • South Carolina

$7,579.78 USD total for 7 nights

Jun 19 – 26, 2027

Primary Suite Balcony Views

Community Pool and MyStay Welcome Gifts

Living Area with Golf Course Views

Kitchen Amenities and Guest Recipe Book

Shipyard Beach Club

10 Townhouse Manor

3 bedrooms·3 baths

Hilton Head Island • South Carolina

$1,137.30 USD total for 3 nights

Sep 22 – 25, 2026

1 Mallard Road: Your 7BR Coastal Getaway with Pool, Hot Tub & Prime Location

1 Mallard Road: Your 7BR Coastal Getaway with Pool, Hot Tub & Prime Location

Game-Ready Living Area with Pool Table & Lounge Seating

Game-Ready Living Area with Pool Table & Lounge Seating

Bonus Sunlit Carolina Room with Foosball and TV Lounge

1 Mallard Road

7 bedrooms·6 baths

Hilton Head Island • South Carolina

$4,785.90 USD total for 4 nights

Sep 22 – 26, 2026

Hilton Head Coligny Beach

Hilton Head Coligny Beach

Hilton Head Coligny Beach

Hilton Head Coligny Beach

Hilton Head Coligny Beach

Hilton Head Coligny Beach

2 bedrooms·2 baths

Hilton Head Island • South Carolina

$360/ night(excl. fees & taxes)

18 Heron Street

18 Heron Street

18 Heron Street

18 Heron Street

18 Heron Street

18 Heron Street

6 bedrooms·6 baths

Hilton Head Island • South Carolina

$3,834.64 USD total for 4 nights

Nov 1 – 5, 2026

13Beach Stop Hilton Head

13Beach Stop Hilton Head

13Beach Stop Hilton Head

13Beach Stop Hilton Head

13Beach Stop Hilton Head

13Beach Stop Hilton Head

3 bedrooms·3 baths

Hilton Head Island • South Carolina

$939.85 USD total for 3 nights

Sep 25 – 28, 2026

301 North Shore Place

301 North Shore Place

301 North Shore Place

Well stocked kitchen

301 North Shore Place

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(155 reviews)

$1,701.90 USD total for 7 nights

Oct 30 – Nov 6, 2026

North Shore Place Rooftop Pool and Hot Tub

Near Beach & Coligny Plaza, Pool, Hot Tub, Patio

Eat Like A Local - Enjoy a Shrimp Boil - Large Pot Provided as well as Receipt

Onsite Rooftop Pool - Swim in the sky or use the hot tub to relax.

Living Room - Stocked with board games, blankets and a pull-out sofa.

Near Beach & Coligny Plaza, Pool, Hot Tub, Patio

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(15 reviews)

$1,009.19 USD $928.27 USD total for 3 nights

Oct 23 – 26, 2026

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

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

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

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

$708.75 USD total for 3 nights

Sep 22 – 25, 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

Seacrest 2512, Walk to Coligny shops/restaurants

Seacrest 2512, Walk to Coligny shops/restaurants

Seacrest 2512, Walk to Coligny shops/restaurants

Seacrest 2512, Walk to Coligny shops/restaurants

Seacrest 2512, Walk to Coligny shops/restaurants

Seacrest 2512, Walk to Coligny shops/restaurants

4 bedrooms·3 baths

Hilton Head Island • South Carolina

5(26 reviews)

$1,232.00 USD total for 3 nights

Dec 16 – 19, 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

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