Location

Dates

Guests

Vacation rentals in Hilton Head Island

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

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

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

$863.89 USD total for 3 nights

Sep 27 – 30, 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

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

Good Times and Tan Lines!-Central air, free bikes!

Good Times and Tan Lines!-Central air, free bikes!

Good Times and Tan Lines!-Central air, free bikes!

Good Times and Tan Lines!-Central air, free bikes!

Good Times and Tan Lines!-Central air, free bikes!

Good Times and Tan Lines!-Central air, free bikes!

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.84(153 reviews)

$901.10 USD total for 4 nights

Sep 27 – Oct 1, 2026

Feelin Tip'Sea-Oceanview Retreat Steps to Beach

Feelin Tip'Sea-Oceanview Retreat Steps to Beach

Feelin Tip'Sea-Oceanview Retreat Steps to Beach

Feelin Tip'Sea-Oceanview Retreat Steps to Beach

Feelin Tip'Sea-Oceanview Retreat Steps to Beach

Feelin Tip'Sea-Oceanview Retreat Steps to Beach

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.8(85 reviews)

$927.50 USD total for 4 nights

Oct 4 – 8, 2026

SHOREthing! Beachside retreat w/ Bikes, Chairs

SHOREthing! Beachside retreat w/ Bikes, Chairs

SHOREthing! Beachside retreat w/ Bikes, Chairs

SHOREthing! Beachside retreat w/ Bikes, Chairs

SHOREthing! Beachside retreat w/ Bikes, Chairs

SHOREthing! Beachside retreat w/ Bikes, Chairs

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.78(275 reviews)

$927.50 USD total for 4 nights

Oct 3 – 7, 2026

Coastal Getaway: Oceanview Condo in Hilton Head

Coastal Getaway: Oceanview Condo in Hilton Head

Coastal Getaway: Oceanview Condo in Hilton Head

Coastal Getaway: Oceanview Condo in Hilton Head

Coastal Getaway: Oceanview Condo in Hilton Head

Coastal Getaway: Oceanview Condo in Hilton Head

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.74(35 reviews)

$695.20 USD total for 3 nights

Oct 5 – 8, 2026

Resort-Style Zero-Entry Pool, Kiddie Splash Zone & Soothing Hot Tub

Lounge with a View

Welcome to Your Slice of Hilton Head Paradise

Elegant Primary Suite with Balcony Views

Welcome to MyStay at 235 Shorewood!

235 Shorewood

3 bedrooms·3 baths

Hilton Head Island • South Carolina

Beach Bliss 2 Bedroom Oceanview Free bikes/chairs!

Beach Bliss 2 Bedroom Oceanview Free bikes/chairs!

Beach Bliss 2 Bedroom Oceanview Free bikes/chairs!

Beach Bliss 2 Bedroom Oceanview Free bikes/chairs!

Beach Bliss 2 Bedroom Oceanview Free bikes/chairs!

Beach Bliss 2 Bedroom Oceanview Free bikes/chairs!

2 bedrooms·2 baths

Hilton Head Island • South Carolina

4.88(261 reviews)

$1,604.00 USD total for 4 nights

Sep 27 – Oct 1, 2026

Oceanfront paradise just steps away to the beach.

Oceanfront paradise just steps away to the beach.

Oceanfront paradise just steps away to the beach.

Oceanfront paradise just steps away to the beach.

Oceanfront paradise just steps away to the beach.

Oceanfront paradise just steps away to the beach.

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(18 reviews)

$1,372.15 USD total for 5 nights

Oct 30 – Nov 4, 2026

Beach Happy!-Nice ocean view Hilton Head Villa

Beach Happy!-Nice ocean view Hilton Head Villa

Beach Happy!-Nice ocean view Hilton Head Villa

Beach Happy!-Nice ocean view Hilton Head Villa

Beach Happy!-Nice ocean view Hilton Head Villa

Beach Happy!-Nice ocean view Hilton Head Villa

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.7(138 reviews)

$901.10 USD total for 4 nights

Sep 30 – Oct 4, 2026

Beach Daze-Gorgeous new shower! Bikes Included

Beach Daze-Gorgeous new shower! Bikes Included

Beach Daze-Gorgeous new shower! Bikes Included

Beach Daze-Gorgeous new shower! Bikes Included

Beach Daze-Gorgeous new shower! Bikes Included

Beach Daze-Gorgeous new shower! Bikes Included

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.87(63 reviews)

$743.20 USD total for 3 nights

Sep 27 – 30, 2026

SeaClusion-Oceanview, Mini split AC, Beach Chairs

SeaClusion-Oceanview, Mini split AC, Beach Chairs

SeaClusion-Oceanview, Mini split AC, Beach Chairs

SeaClusion-Oceanview, Mini split AC, Beach Chairs

SeaClusion-Oceanview, Mini split AC, Beach Chairs

SeaClusion-Oceanview, Mini split AC, Beach Chairs

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.75(188 reviews)

$677.20 USD total for 3 nights

Oct 12 – 15, 2026

Salty Sand-Close to the pool, steps to the beach!

Salty Sand-Close to the pool, steps to the beach!

Salty Sand-Close to the pool, steps to the beach!

Salty Sand-Close to the pool, steps to the beach!

Salty Sand-Close to the pool, steps to the beach!

Salty Sand-Close to the pool, steps to the beach!

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.74(199 reviews)

$1,015.50 USD total for 4 nights

Oct 3 – 7, 2026

Gorgeous view of the ocean from the balcony

Fully equipped kitchen

Updated pool deck

Shore Beats Work!-Stunning view 3 from ocean front

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.74(101 reviews)

$125 – $259/ night(excl. fees & taxes)