Your Beach House Getaway With 6-Seater Golf Cart included with your stay!
6 Seater Electric Golf Cart- INCLUDED w/ stay!
Private pool, patio, plenty of seating, smart TV
Kitchen with eat in island
Living room

91 Sandcastle Court

5 bedrooms·5 baths
Hilton Head Island • South Carolina
5(44 reviews)

$3,087.07 USD total for 3 nights

Sep 29 – Oct 2, 2026

Front of house
Over head view of pool and hot tub from front porch
Arial view from front of home
Burkes Beach access just a few minutes walk from the house
New Kitchen and appliances

Luxury beach house w/pool, elevator, game room. Steps to Beach

8 bedrooms·7 baths
Hilton Head Island • South Carolina
5(34 reviews)

$5,618.46 USD total for 3 nights

Oct 2 – 5, 2026

5 Sandy Beach Trail-4th row from the beach
Steps From The Beach! A few minute walk to beach access!
Main Level King Bedroom, fresh duvet cover, smart TV, private bathroom
Cozy Queen Bedroom on Main level w/ fresh duvet cover, smart TV and private bath
5 Sandy Beach Trail

5 Sandy Beach Trail

6 bedrooms·6½ baths
Hilton Head Island • South Carolina
5(8 reviews)

$4,367.87 USD total for 3 nights

Oct 4 – 7, 2026

HHBT c258
HHBT c258
HHBT c258
Wireless charging on every end table! Smart TV and new furniture added march 2021.
HHBT c258

HHBT c258

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.83(188 reviews)

$610.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

Luxury Balcony..steps to beach
Elegant bath vanity with brass fixtures and charming botanical wallpaper
Serene king bedroom with luxe linens, soft lighting, and elegant decor
Private oceanfront balcony with stunning beach views and morning coffee vibes
Sunny dining nook with stylish seating and a bright, airy feel

Direct Oceanfront|KING BED-Luxe Balcony w/Sunrises

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(39 reviews)

$1,673.99 USD total for 3 nights

Oct 12 – 15, 2026

New Designer Direct BeachFront Condo w/Panoramic Ocean View!
RARE Expanded Bedroom w/KING BED & 65” SmartTV! Enjoy your downtime watching FREE NETFLIX & CABLE! (Prime, Hulu, etc. bring your passwords.)
Sunrise over the Ocean from your Balcony!
Largest Oceanfront Pool on Hilton Head Island w/Tiki Bar & Grill!
All new kitchen features full-sized stainless appliances, stone counters & custom backsplash! (Stocked with all common cooking utensils & supplies!)

Oceanfront Designer KING BED💙Beach Bar+2Pools GYM

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.97(200 reviews)

$3,654.12 USD total for 7 nights

Oct 20 – 27, 2026

Newly Remodeled Designer unit has gorgeous Lowcountry Marsh & Ocean views from patio!! Quiet and private--No Parking Lot or Pool Noise!! Top floor, end unit! No footsteps above!
KING BED, SmartTV & 2 closets! Roomy with super soft sheets and cozy new mattress!
Our unit is Steps to Beach & largest Ocean Front pool on Hilton Head Island!!
Panoramic Marsh & Ocean views from our covered patio! Straight ahead and to the left, enjoy serene Lowcountry Marsh views! Ocean view is to the right—you can see the waves depending upon tides! Marsh NOT noisy parking lot below!
Fully equipped kitchen has all new cabinets, full-size stainless appliances, granite & marble!

Ocean View w/KING BED💙Beach Bar 2Pools GYM+Tennis

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(190 reviews)

$3,257.85 USD total for 7 nights

Oct 18 – 25, 2026

Sunset over HHI.... gorgeous sight
NEW Kitchen with farm sink, 42" cabinets. stainless appliances
Awesome TV pic when on HD channels. Bring your ROKU and Netflicks passwords too
ADMIRALS ROW 2/2 - HH Beach & Tennis Resort condo
Voted one of the 10 Best Beaches in the US

ADMIRALS ROW 2/2 - HH Beach & Tennis Resort condo

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$2,469.75 USD total for 7 nights

Sep 29 – Oct 6, 2026

Big Ocean & Pool Views from private 3rd floor balcony!
KING BED & 65" HD SmartTV with free Netflix & Amazon Prime! Rare enlarged bedroom!
100% New renovation by HGTV featured designer!
All new fully-stocked designer kitchen with full-size stainless appliances & marble backsplash!
Oceanview Designer! KING BED Bar! 65"TV Tennis GYM

Oceanview Designer! KING BED Bar! 65"TV Tennis GYM

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(31 reviews)

$3,221.46 USD total for 7 nights

Oct 17 – 24, 2026

Panoramic Oceanfront Views the moment you open the door! All New Luxury condo designed by an HGTV featured decorator! Stunning unobstructed views of the Ocean, Pool, Coastal Marsh & Dunes!
An HGTV featured decorator just completed a 100% NEW renovation on April 2023 - featuring luxurious Coastal Décor, utilizing a soothing Sand & Sea Color Palette!
Oceanfront Balcony offers views of the Ocean and Beautiful Coastal Marsh with its Windswept Dune Trees!
Sunrise from your Beachfront Balcony!
KING BED in Expanded Bedroom! Highly Rated 12” Memory Foam Mattress. 65" SmartTV w/ FREE Netflix, Prime & Cable TV!

Oceanfront Luxury! KING BED 75"TV Pickleball & BAR

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.93(59 reviews)

$4,076.46 USD total for 7 nights

Sep 29 – Oct 6, 2026

Beach Skybox HHI - panoramic view
Beach Skybox HHI - panoramic view
Beach Skybox HHI - panoramic view
Beach Skybox HHI - panoramic view
Beach Skybox HHI - panoramic view

Beach Skybox HHI - panoramic view

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(201 reviews)

$924.00 USD total for 3 nights

Oct 4 – 7, 2026

Directly on the Beach!
Directly on the Beach!
Directly on the Beach!
Directly on the Beach!
Directly on the Beach!

Directly on the Beach!

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$2,520.00 USD total for 7 nights

Sep 29 – Oct 6, 2026

2519 Villamare
Community Pool 1 of 3 with Children's Area
Primary King Suite with Private Balcony & Coastal Views
Family-Friendly Suite with Ocean Views & Private Balcony
Ocean Views from Your Living & Dining Room

2519 Villamare

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$4,112.09 USD total for 3 nights

Mar 11 – 14, 2027

1405 Villamare in Palmetto Dunes, Hilton Head
1405 Villamare in Palmetto Dunes, Hilton Head
1405 Villamare in Palmetto Dunes, Hilton Head
1405 Villamare in Palmetto Dunes, Hilton Head
1405 Villamare in Palmetto Dunes, Hilton Head

1405 Villamare in Palmetto Dunes, Hilton Head

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(136 reviews)

$1,864.50 USD $1,699.50 USD total for 7 nights

Dec 13 – 20, 2026

Look out over the ocean while relaxing in living room!
1404 Villamare in Palmetto Dunes, Hilton Head
1404 Villamare in Palmetto Dunes, Hilton Head
1404 Villamare in Palmetto Dunes, Hilton Head
1404 Villamare in Palmetto Dunes, Hilton Head

1404 Villamare in Palmetto Dunes, Hilton Head

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.94(204 reviews)

$1,314.50 USD total for 5 nights

Nov 14 – 19, 2026

Living Room Area
View from Main Balcony of Adults-Only Pool
Primary King Bedroom with Entrance to Balcony and Desk
Birdseye View of Villamare!
Communal Fire Pit

1208 Villamare

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$1,737.88 USD total for 3 nights

Oct 17 – 20, 2026

View from the living room swivel chair.
Living Room with new La-Z-Boy sofa & Love Seat
Dining table with 6 chairs
Living Room with new furnishings.
Main Suite with King Bed.

Villamare 3328, 5 stars, Ocean views

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

$2,280.53 USD $1,878.04 USD total for 7 nights

Oct 3 – 10, 2026

Family Room
Family Pool and Hot Tub
Serenity Pool and Hot Tub
Master Bedroom
Guest Bedroom

Oceanfront Listing! 3125 Villamare

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(58 reviews)

$2,226.30 USD $1,820.04 USD total for 3 nights

Sep 29 – Oct 2, 2026

Oceanfront Villamare 3524!
Oceanfront Villamare 3524!
Oceanfront Villamare 3524!
Oceanfront Villamare 3524!
Oceanfront Villamare 3524!

Oceanfront Villamare 3524!

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(36 reviews)

$5,610.00 USD total for 7 nights

Mar 13 – 20, 2027

Premium Ocean Views
Bright Modern Living Room with Oceanview Balcony
Stunning View from Your Private Balcony
Bright Modern Living Room with Oceanview Balcony
Spacious Primary Suite with Plush Bedding

4405 Windsor Court North

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$1,321.72 USD total for 3 nights

Oct 10 – 13, 2026

18 Heron Street
18 Heron Street
18 Heron Street
18 Heron Street
18 Heron Street

18 Heron Street

6 bedrooms·6 baths
Hilton Head Island • South Carolina

$3,834.64 USD total for 4 nights

Nov 1 – 5, 2026

Breakers 220 ocean View Coligny Beach Hilton Head
Private kitchen
Beach
Living area
Exterior

Breakers 220 Oceanfront Condo – Direct Beach Access & Elevator

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.9(59 reviews)

$657.51 USD total for 3 nights

Sep 29 – Oct 2, 2026

Breakers 328 Collage
Building Breakers 328 Hilton Head SC
Interior
living room with Ocean View
Bedroom with Built ins and reading lights at head of Bed w USB chargers, roku smart tv

Breakers 328 Oceanfront Hilton Head Condo Direct Beach Access

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

$743.43 USD total for 3 nights

Sep 29 – Oct 2, 2026

Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access
Breakers 324 Hilton Head Ocean view from Balcony
Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access
Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access
Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access

Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access

1 bedroom·1 bath
Hilton Head Island • South Carolina

$678.99 USD total for 3 nights

Nov 1 – 4, 2026