Subtropical Stunner-King bed & bikes! Central Air!
Subtropical Stunner-King bed & bikes! Central Air!
Subtropical Stunner-King bed & bikes! Central Air!
Subtropical Stunner-King bed & bikes! Central Air!
Subtropical Stunner-King bed & bikes! Central Air!

Subtropical Stunner-King bed & bikes! Central Air!

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(210 reviews)

$989.10 USD total for 4 nights

Oct 12 – 16, 2026

Just Beachy Hilton Head Island
Just Beachy Hilton Head Island
Steps to the Beach
Just Beachy Hilton Head Island
Just Beachy Hilton Head Island

Just Beachy Hilton Head Island

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.83(53 reviews)

$621.60 USD total for 3 nights

Sep 29 – Oct 2, 2026

Sandy Feet Retreat-New Shower-Bikes Incl-Oceanview
Sandy Feet Retreat-New Shower-Bikes Incl-Oceanview
Sandy Feet Retreat-New Shower-Bikes Incl-Oceanview
Sandy Feet Retreat-New Shower-Bikes Incl-Oceanview
Sandy Feet Retreat-New Shower-Bikes Incl-Oceanview

Sandy Feet Retreat-New Shower-Bikes Incl-Oceanview

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(289 reviews)

$945.10 USD total for 4 nights

Oct 23 – 27, 2026

Sunset Dunes Direct Beach Access
Sunset Dunes Direct Beach Access
Sunset Dunes Direct Beach Access
Sunset Dunes Direct Beach Access
Sunset Dunes Direct Beach Access

Sunset Dunes Direct Beach Access

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(167 reviews)

$710.20 USD total for 3 nights

Oct 14 – 17, 2026

View of the ocean from the balcony
Queen bed
Newly purchased queen sleeper sofa 1/26
55" smart tv
SS2 Pool

Just Beachy! Absolute top notch design, Oceanviews

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.89(157 reviews)

$901.10 USD total for 4 nights

Oct 5 – 9, 2026

Seabatical-Beautiful ocean view! w/Bikes & Chairs
Seabatical-Beautiful ocean view! w/Bikes & Chairs
Seabatical-Beautiful ocean view! w/Bikes & Chairs
Seabatical-Beautiful ocean view! w/Bikes & Chairs
Seabatical-Beautiful ocean view! w/Bikes & Chairs

Seabatical-Beautiful ocean view! w/Bikes & Chairs

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.88(304 reviews)

$901.10 USD total for 4 nights

Oct 24 – 28, 2026

Crashin' Waves-Oceanview w/Bikes, Chairs& King Bed
Crashin' Waves-Oceanview w/Bikes, Chairs& King Bed
Crashin' Waves-Oceanview w/Bikes, Chairs& King Bed
Crashin' Waves-Oceanview w/Bikes, Chairs& King Bed
Crashin' Waves-Oceanview w/Bikes, Chairs& King Bed

Crashin' Waves-Oceanview w/Bikes, Chairs& King Bed

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.84(333 reviews)

$1,065.00 USD total for 4 nights

Oct 17 – 21, 2026

Seascape Villas
Seascape Villas
Seascape Villas
Seascape Villas
Seascape Villas

Seascape Villas

1 bedroom·1 bath
Hilton Head Island • South Carolina

$2,500.00 USD total for 30 nights

Dec 1 – 31, 2026

Beautiful Couples Retreat Oceanview w/Bikes&Chairs
Beautiful Couples Retreat Oceanview w/Bikes&Chairs
Beautiful Couples Retreat Oceanview w/Bikes&Chairs
Beautiful Couples Retreat Oceanview w/Bikes&Chairs
Beautiful Couples Retreat Oceanview w/Bikes&Chairs

Beautiful Couples Retreat Oceanview w/Bikes&Chairs

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.9(411 reviews)

$776.20 USD total for 3 nights

Sep 30 – Oct 3, 2026

SerenityByTheSea-Couples Retreat-King,Bikes,Chairs
SerenityByTheSea-Couples Retreat-King,Bikes,Chairs
SerenityByTheSea-Couples Retreat-King,Bikes,Chairs
SerenityByTheSea-Couples Retreat-King,Bikes,Chairs
SerenityByTheSea-Couples Retreat-King,Bikes,Chairs

SerenityByTheSea-Couples Retreat-King,Bikes,Chairs

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.88(309 reviews)

$989.10 USD total for 4 nights

Sep 29 – Oct 3, 2026

Gone Coastal! 2 from oceanfront! Central air!
Gone Coastal! 2 from oceanfront! Central air!
Gone Coastal! 2 from oceanfront! Central air!
Gone Coastal! 2 from oceanfront! Central air!
Gone Coastal! 2 from oceanfront! Central air!

Gone Coastal! 2 from oceanfront! Central air!

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.67(120 reviews)

$927.50 USD total for 4 nights

Apr 1 – 5, 2027

Coastal Soul-Gorgeous Direct OceanFront!
Coastal Soul-Gorgeous Direct OceanFront!
Coastal Soul-Gorgeous Direct OceanFront!
Coastal Soul-Gorgeous Direct OceanFront!
Coastal Soul-Gorgeous Direct OceanFront!

Coastal Soul-Gorgeous Direct OceanFront!

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(73 reviews)

$1,807.50 USD total for 4 nights

Jun 2 – 6, 2027

A serene getaway at the beach
Roku smart TV in the Living Room
All appliances, utensils and cookware you will need to prepare meals.
Comfortable Queen bed in the primary bedroom
Smart TV for your private viewing

HHI Hidden Dunes

2 bedrooms·1 bath
Hilton Head Island • South Carolina
5(146 reviews)

$483.00 USD total for 3 nights

Oct 1 – 4, 2026

Sea Pines Serenity
Sea Pines Serenity
Sea Pines Serenity
Sea Pines Serenity
Sea Pines Serenity

Sea Pines Serenity

3 bedrooms·2 baths
Hilton Head Island • South Carolina
5(4 reviews)

$2,073.00 USD total for 4 nights

Oct 18 – 22, 2026

Small density complex with 2 assigned parking spots right across from beach!
Fully equipped kitchen with table for 2
Granite countertops
Light and bright living area with neutral furniture
Spacious King Master with Roku TV

Steel City Escape - Ocean Gate next to Sea Pines

2 bedrooms·2½ baths
Hilton Head Island • South Carolina
5(50 reviews)

$1,054.50 USD total for 3 nights

Oct 3 – 6, 2026

Living Room
Living Room
Living Room/Dining
Living Room/Dining
Living Room/Dining/Kitchen

309 Ocean Dunes Villas

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.81(190 reviews)

$2,651.50 USD total for 7 nights

Oct 23 – 30, 2026

Front of home
Hilton Head Sea Pines Getaway
Hilton Head Sea Pines Getaway
Foyer/entry way
Hilton Head Sea Pines Getaway

Hilton Head Sea Pines Getaway

5 bedrooms·3½ baths
Hilton Head Island • South Carolina
4.85(82 reviews)

$1,813.26 USD total for 3 nights

Sep 29 – Oct 2, 2026

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access
Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access
Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access
Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access
Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access

2 bedrooms·2½ baths
Hilton Head Island • South Carolina
4.98(103 reviews)

$3,445.00 USD total for 3 nights

Oct 11 – 14, 2026

Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access
Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access
Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access
Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access
Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access

Best of Harbour Town - Beach | Pool | Golf | 3BR/3BA - Book for Summer - Pool Access

3 bedrooms·3 baths
Hilton Head Island • South Carolina
4.95(81 reviews)

$3,465.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

SEA PINES 4 Bed + Loft
SEA PINES 4 Bed + Loft
SEA PINES 4 Bed + Loft
SEA PINES 4 Bed + Loft
SEA PINES 4 Bed + Loft

SEA PINES 4 Bed + Loft

4 bedrooms·4 baths
Hilton Head Island • South Carolina
4.9(188 reviews)

$2,331.00 USD total for 4 nights

Oct 7 – 11, 2026

Aerial view
Front of home
Entryway
Entryway
Kitchen view into living area

Hilton Head Lagoon Paradise in Deer Run

5 bedrooms·5 baths
Hilton Head Island • South Carolina
5(4 reviews)

$2,142.86 USD total for 3 nights

Jun 2 – 5, 2027

Tranquility By The Beach: 12th Row From the Water image 1
Tranquility By The Beach: 12th Row From the Water image 2
Take a dip in the evening
Tranquility By The Beach: 12th Row From the Water image 4
The dining table can accommodate the entire family

Tranquility By The Beach: 12th Row From the Water

5 bedrooms·3½ baths
Hilton Head Island • South Carolina
4.93(59 reviews)

$6,721.50 USD total for 7 nights

Oct 27 – Nov 3, 2026

Sleeps 12! 5 BDRM-2 Kings,3 Queens-Deck & Patio-Mins to PI & Beaufort
Sleeps 12! 5 BDRM-2 Kings,3 Queens-Deck & Patio-Mins to PI & Beaufort
Horseshoe pit in the back yard.
Sleeps 12! 5 BDRM-2 Kings,3 Queens-Deck & Patio-Mins to PI & Beaufort
Sleeps 12! 5 BDRM-2 Kings,3 Queens-Deck & Patio-Mins to PI & Beaufort

Sleeps 12! 5 BDRM-2 Kings,3 Queens-Deck & Patio-Mins to PI & Beaufort

5 bedrooms·2 baths
Port Royal • South Carolina
5(49 reviews)

$807.23 USD total for 3 nights

Oct 3 – 6, 2026

Living area looking into dining and kitchen area.
Walk to DT Beaufort|15 min ride to PI & Port Royal
Quartz countertops, tile backsplash and locally sourced heart pine floating shelves.
Walk to DT Beaufort|15 min ride to PI & Port Royal
Furnished back deck.

Walk to DT Beaufort|15 min ride to PI & Port Royal

4 bedrooms·2 baths
Beaufort • South Carolina
5(142 reviews)

$679.52 USD total for 3 nights

Oct 3 – 6, 2026