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

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 23 – 26, 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.
Community Pool
View from balcony

Best location on HHI! Oceanfront + Walkable

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(47 reviews)

$912.60 USD total for 3 nights

Oct 8 – 11, 2026

Stay Seaside
Stay Seaside
Stay Seaside
Queen Sleeper Sofa
Stay Seaside

Stay Seaside

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(108 reviews)

$957.50 USD total for 3 nights

Sep 23 – 26, 2026

View of the ocean from the balcony
King bed
Queen sleeper sofa
Pool in the evening
Wide beach

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

Sep 28 – Oct 1, 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

Seaside 2 pool
everything need to cook meals
Queen bed
Gorgeous stand up shower
Coastal Blue – Oceanview Condo in the Heart of Hil image 5

Coastal Blue – Oceanview Condo in the Heart of Hil

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.88(24 reviews)

$728.20 USD total for 3 nights

Sep 23 – 26, 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)

$901.10 USD total for 4 nights

Oct 15 – 19, 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

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

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

Pool view
Third floor balcony overlooking your tropical oasis
Master bathroom
Hilton Head Vacation Getaway
Hilton Head Vacation Getaway

Hilton Head Vacation Getaway

3 bedrooms·2 baths
Hilton Head Island • South Carolina
4.47(15 reviews)

$1,032.50 USD $866.00 USD total for 3 nights

Sep 23 – 26, 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