Location

Dates

Guests

Vacation rentals in Hilton Head Island

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

Beautiful view of the ocean from the balcony!

OceanEscape – Steps to the Beach image 2

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 total for 3 nights

Sep 24 – 27, 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

Elegance at the beach -Ocean View Villa, Gorgeous!

Elegance at the beach -Ocean View Villa, Gorgeous!

Elegance at the beach -Ocean View Villa, Gorgeous!

Elegance at the beach -Ocean View Villa, Gorgeous!

Elegance at the beach -Ocean View Villa, Gorgeous!

Elegance at the beach -Ocean View Villa, Gorgeous!

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.87(275 reviews)

$901.10 USD total for 4 nights

Sep 25 – 29, 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

The fan/light in the bedroom has 3 speeds and the LED light can change to any color!

The unit is located just steps from the beach!

3 barstools at the dining/workspace. The TVs are both 50 inch Samsung. Cable is provided and you can stream Netflix and YouTube from the cable box.

View from balcony

Best location on HHI! Oceanfront + Walkable

1 bedroom·1 bath

Hilton Head Island • South Carolina

5(47 reviews)

$907.10 USD total for 3 nights

Oct 8 – 11, 2026

View of the ocean from the balcony

Queen sleeper sofa

Pool in the evening

Pelican Roost at Seaside Steps to the Beach

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.88(24 reviews)

$715.00 USD total for 3 nights

Oct 18 – 21, 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

SeaGem-Oceanview! Last min disc! Many Upgrades New Reno

SeaGem-Oceanview! Last min disc! Many Upgrades New Reno

SeaGem-Oceanview! Last min disc! Many Upgrades New Reno

SeaGem-Oceanview! Last min disc! Many Upgrades New Reno

SeaGem-Oceanview! Last min disc! Many Upgrades New Reno

SeaGem-Oceanview! Last min disc! Many Upgrades New Reno

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.71(178 reviews)

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

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

Tranquility on the Water - 2 Bedroom!

Tranquility on the Water - 2 Bedroom!

Tranquility on the Water - 2 Bedroom!

Tranquility on the Water - 2 Bedroom!

Tranquility on the Water - 2 Bedroom!

Tranquility on the Water - 2 Bedroom!

2 bedrooms·1½ baths

Hilton Head Island • South Carolina

4.9(90 reviews)

$849.25 USD total for 3 nights

Oct 5 – 8, 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

Coastal Nest - Oceanviews! Near Coligny

Coastal Nest - Oceanviews! Near Coligny

Coastal Nest - Oceanviews! Near Coligny

Coastal Nest - Oceanviews! Near Coligny

Coastal Nest - Oceanviews! Near Coligny

Coastal Nest - Oceanviews! Near Coligny

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.82(56 reviews)

$901.10 USD total for 4 nights

Oct 11 – 15, 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

Flip Flop Paradise-Steps to the Sand! Free Bikes

Flip Flop Paradise-Steps to the Sand! Free Bikes

Flip Flop Paradise-Steps to the Sand! Free Bikes

Flip Flop Paradise-Steps to the Sand! Free Bikes

Flip Flop Paradise-Steps to the Sand! Free Bikes

Flip Flop Paradise-Steps to the Sand! Free Bikes

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.82(215 reviews)

$989.10 USD total for 4 nights

Sep 30 – Oct 4, 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

SeaRenity! Beautiful Reno! King bed! w/Bikes

SeaRenity! Beautiful Reno! King bed! w/Bikes

SeaRenity! Beautiful Reno! King bed! w/Bikes

SeaRenity! Beautiful Reno! King bed! w/Bikes

SeaRenity! Beautiful Reno! King bed! w/Bikes

SeaRenity! Beautiful Reno! King bed! w/Bikes

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.81(202 reviews)

$743.20 USD total for 3 nights

Sep 29 – Oct 2, 2026

Reel Paradise-Beautiful escape! Bikes & Chairs

Reel Paradise-Beautiful escape! Bikes & Chairs

Reel Paradise-Beautiful escape! Bikes & Chairs

Reel Paradise-Beautiful escape! Bikes & Chairs

Reel Paradise-Beautiful escape! Bikes & Chairs

Reel Paradise-Beautiful escape! Bikes & Chairs

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.84(209 reviews)

$945.10 USD total for 4 nights

Sep 28 – Oct 2, 2026

Shore To Please! Oceanview couples retreat w/bikes

Shore To Please! Oceanview couples retreat w/bikes

Shore To Please! Oceanview couples retreat w/bikes

Shore To Please! Oceanview couples retreat w/bikes

Shore To Please! Oceanview couples retreat w/bikes

Shore To Please! Oceanview couples retreat w/bikes

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.87(329 reviews)

$945.10 USD total for 4 nights

Sep 26 – 30, 2026