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

Brand new gorgeous shower
SunnyDaze-Brand new reno- King bed, Free bikes! image 2
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

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

BEach Happy HHI, Steps to the Beach
BEach Happy HHI, Steps to the Beach
BEach Happy HHI, Steps to the Beach
BEach Happy HHI, Steps to the Beach
BEach Happy HHI, Steps to the Beach

BEach Happy HHI, Steps to the Beach

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.91(95 reviews)

$621.60 USD total for 3 nights

Sep 22 – 25, 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

Unmatched views of the ocean and beach. This location on the island can not be beat.
Perfect cozy spot to relax at night and take in the ocean breeze.
Wavefront Bliss: Your Hilton Head Coastal Escape
Perfect sunset views!
Wavefront Bliss: Your Hilton Head Coastal Escape

Wavefront Bliss: Your Hilton Head Coastal Escape

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.83(30 reviews)

$655.00 USD total for 3 nights

Oct 20 – 23, 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

Beachin It!-Oceanview Updated 2024, King Bed Bikes
Beachin It!-Oceanview Updated 2024, King Bed Bikes
Beachin It!-Oceanview Updated 2024, King Bed Bikes
Beachin It!-Oceanview Updated 2024, King Bed Bikes
Beachin It!-Oceanview Updated 2024, King Bed Bikes

Beachin It!-Oceanview Updated 2024, King Bed Bikes

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.78(237 reviews)

$927.50 USD total for 4 nights

Sep 27 – Oct 1, 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