Location

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Vacation rentals in Hilton Head Island

Spacious 3BR, Minutes to the Beach, Sleeps 8 &Pets image 1

Spacious 3BR, Minutes to the Beach, Sleeps 8 &Pets image 2

Spacious 3BR, Minutes to the Beach, Sleeps 8 &Pets image 4

Spacious 3BR, Minutes to the Beach, Sleeps 8 &Pets image 5

Spacious 3BR, Minutes to the Beach, Sleeps 8 &Pets image 6

Lazy Dog Villa - Shipyard Hilton Head SC

3 bedrooms·3½ baths

Hilton Head Island • South Carolina

4.89(122 reviews)

$1,038.22 USD total for 3 nights

Oct 11 – 14, 2026

Spacious living room with view of 6th hole Galleon golf course.

Spacious open first floor.

Large screen HDTV, 300 Mbps, 125+Spectrum channels.

Shipyard Beach at sunset

121 The Greens

2 bedrooms·2 baths

Hilton Head Island • South Carolina

4.92(63 reviews)

$1,025.64 USD total for 3 nights

Nov 6 – 9, 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

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

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

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

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)

$819.75 USD total for 3 nights

Sep 25 – 28, 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

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 22 – 25, 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 22 – 25, 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

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 22 – 26, 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

$1,894.27 USD total for 3 nights

Sep 26 – 29, 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

Sep 27 – Oct 1, 2026