Starboard Building at Captain's Quarters- gated
The Pearl looks out over the Intracoastal waterway
Looking from the boardwalk across Broad Creek- at Disney
Off the Starboard elevator-stairway at end of this hallway-turn left to enter The Pearl
Wheelchair accesible

The Pearl at Shelter Cove in Palmetto Dunes Resort

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(38 reviews)

$1,327.56 USD total for 4 nights

Sep 29 – Oct 3, 2026

Private Heated Pool, Hot Tub, Clean, King Bed
Private Heated Pool, Hot Tub, Clean, King Bed
Private Heated Pool, Hot Tub, Clean, King Bed
Private Heated Pool, Hot Tub, Clean, King Bed
Private Heated Pool, Hot Tub, Clean, King Bed

Private Heated Pool, Hot Tub, Clean, King Bed

4 bedrooms·3 baths
Hilton Head Island • South Carolina
5(75 reviews)

$4,490.38 USD total for 5 nights

Oct 10 – 15, 2026

View to the backyard and golf course.
Welcome to your home away from home!
Talk, play games, and chill in the living room.
OffShoreDreaming
The powder room is located off the living room. Superhero included.

OffShoreDreaming

3 bedrooms·3 baths
Hilton Head Island • South Carolina
4.94(18 reviews)

$1,805.43 USD total for 3 nights

Sep 29 – Oct 2, 2026

Private pool
Gorgeous, Contemporary 3 Bedroom House
Gorgeous, Contemporary 3 Bedroom House
Front of the house
Gorgeous, Contemporary 3 Bedroom House

Gorgeous, Contemporary 3 Bedroom House

3 bedrooms·2 baths
Hilton Head Island • South Carolina
4.87(23 reviews)

$2,668.75 USD $2,432.88 USD total for 5 nights

Sep 29 – Oct 4, 2026

Bishop’s Beachside Retreat
Bishop’s Beachside Retreat
Bishop’s Beachside Retreat
Bishop’s Beachside Retreat
Bishop’s Beachside Retreat

Bishop’s Beachside Retreat

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$1,083.50 USD total for 3 nights

Sep 29 – Oct 2, 2026

Hilton Head_Coastal Breeze Beach Getaway
Large outdoor pool at bldg 1 with seasonal poolside restaurant The Beach Bear. Heated outdoor pool starting March 1st.
Eat in dining for 6.
Outdoor Pool at bldg 4 our building.
Coastal Breeze -Top Floor - Hilton Head Island image 4

Hilton Head_Coastal Breeze Beach Getaway

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(134 reviews)

$763.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

View of Living Area from Dining Area and Kitchen
2nd Bedroom sleeps 3
Living Area - new sofa (May 2026) not pictured here
Living Area
Living Area- new sofa (May 2026) not pictured here

Seashells by the Sea at Hilton Head Resort

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.88(67 reviews)

$572.22 USD total for 3 nights

Sep 29 – Oct 2, 2026

Resort Daze-2 Bedroom, Short Walk to the Beach
Resort Daze-2 Bedroom, Short Walk to the Beach
Resort Daze-2 Bedroom, Short Walk to the Beach
Resort Daze-2 Bedroom, Short Walk to the Beach
Resort Daze-2 Bedroom, Short Walk to the Beach

Resort Daze-2 Bedroom, Short Walk to the Beach

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.87(77 reviews)

$954.60 USD total for 4 nights

Sep 29 – Oct 3, 2026

Resort Breeze-2 BR, Pools, Hot Tub, Tennis, Beach
Resort Breeze-2 BR, Pools, Hot Tub, Tennis, Beach
Resort Breeze-2 BR, Pools, Hot Tub, Tennis, Beach
Resort Breeze-2 BR, Pools, Hot Tub, Tennis, Beach
Resort Breeze-2 BR, Pools, Hot Tub, Tennis, Beach

Resort Breeze-2 BR, Pools, Hot Tub, Tennis, Beach

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.85(73 reviews)

$954.60 USD total for 4 nights

Sep 29 – Oct 3, 2026

12 Crabline Court
12 Crabline Court
12 Crabline Court
12 Crabline Court
12 Crabline Court

12 Crabline Court

6 bedrooms·6½ baths
Hilton Head Island • South Carolina

$3,219.00 USD total for 3 nights

Oct 4 – 7, 2026

15 Crabline
15 Crabline
15 Crabline
15 Crabline
15 Crabline

15 Crabline

8 bedrooms·6½ baths
Hilton Head Island • South Carolina
4.88(34 reviews)

$3,219.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

19 Crabline Court
19 Crabline Court
19 Crabline Court
19 Crabline Court
19 Crabline Court

19 Crabline Court

6 bedrooms·6 baths
Hilton Head Island • South Carolina

$2,734.50 USD total for 3 nights

Sep 29 – Oct 2, 2026

Bright and Inviting Living Room with direct access to Private Screened Balcony Open floor plan for kitchen, dining and living areas
The condo is bright & inviting, clean and a coastal decor setting a relaxing mood for your stay
NEWLY REMODELED KITCHEN: Big SS sink, white quartz countertops, eating bar w/ stools, cooking basics, stainless steel appliances, dishwasher, toaster, drip coffee maker, 2 blenders, ceramic nonstick cookware, pantry closet w/ basic cooking essentials
Master Bedroom with Comfortable King Size Bed , Black Out Curtains, Hardwood Floors New Smart TV, Himalayan Salt Lamp and Alarm Clock
Dining table for 4 and an eating bar w/ stools for 2

Island Paradise! Entire Villa

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$794.38 USD total for 3 nights

Sep 29 – Oct 2, 2026

Hilton Head Vacation Rental
Hilton Head Vacation Rental
Hilton Head Vacation Rental
Hilton Head Vacation Rental
Hilton Head Vacation Rental

Hilton Head Vacation Rental

2 bedrooms·2 baths
Hilton Head Island • South Carolina
$299/ night(excl. fees & taxes)
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

Exterior Front View - Driveway can hold 4 Cars, Garage Can Hold 2 Cars
Entryway 2nd Floor
Front Porch Landing
2nd Floor Great Room
Kitchen View with Large Island and Seating for 4

Fully Screened Heated Pool/Elevator/Fenced-79

6 bedrooms·4 baths
Hilton Head Island • South Carolina
4.94(126 reviews)

$2,817.10 USD total for 3 nights

Sep 29 – Oct 2, 2026

Family Room
Exterior Front
Kitchen
Kitchen
Beverage Area

The Hilton Head Haven

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.93(28 reviews)

$1,595.00 USD total for 4 nights

Sep 29 – Oct 3, 2026

Bright open dining space with full kitchen, bar seating, and in-unit laundry
Pet-Friendly 3BR Villa Walk to Beach, Golf, Tennis
Pet-Friendly 3BR Villa Walk to Beach, Golf, Tennis
Pet-Friendly 3BR Villa Walk to Beach, Golf, Tennis
Pet-Friendly 3BR Villa Walk to Beach, Golf, Tennis

Pet-Friendly 3BR Villa Walk to Beach, Golf, Tennis

3 bedrooms·2½ baths
Hilton Head Island • South Carolina

$979.59 USD $938.49 USD total for 3 nights

Sep 29 – Oct 2, 2026

Front Exterior View, Driveway holds 4 Cars, Garage Holds Two Cars.
Exterior Stairs To Front Door
Front Porch Landing
Entry from Front Door
Entry From Front Door

Fully Screened Heated Pool/Elevator/Fenced-51

6 bedrooms·4 baths
Hilton Head Island • South Carolina
4.92(167 reviews)

$2,954.82 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

Living Area
Entry to Villa
Entry hall
Primary Bedroom with King Bed
Primary Bath with full tub

Coastal Calm Retreat in Palmetto Dunes

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(1 review)

$631.05 USD total for 3 nights

Sep 29 – Oct 2, 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

Coastal Charm - Beach, pickleball, golf, pets image 1
Coastal Charm - Beach, pickleball, golf, pets image 2
Coastal Charm - Beach, pickleball, golf, pets image 3
Coastal Charm - Beach, pickleball, golf, pets image 4
Kitchen with counter and stools

Coastal Charm Pets n Family Palmetto Dunes QG

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.91(270 reviews)

$1,099.60 USD total for 3 nights

Oct 3 – 6, 2026

HHI TIDE 21 at Hilton Head Beach & Tennis Resort
HHI TIDE 21 at Hilton Head Beach & Tennis Resort
HHI TIDE 21 at Hilton Head Beach & Tennis Resort
HHI TIDE 21 at Hilton Head Beach & Tennis Resort
HHI TIDE 21 at Hilton Head Beach & Tennis Resort

HHI TIDE 21 at Hilton Head Beach & Tennis Resort

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(201 reviews)

$686.57 USD total for 3 nights

Oct 25 – 28, 2026