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

Captain’s Quarters on the Water
Captain’s Quarters on the Water
Captain’s Quarters on the Water
Captain’s Quarters on the Water
Captain’s Quarters on the Water

Captain’s Quarters on the Water

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(49 reviews)

$2,147.00 USD total for 7 nights

Sep 29 – Oct 6, 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

Fairway-Facing Fun: Family Games & Serene Backyard
Welcome to 72 Off Shore! Enjoy Our New Pool, Spa & Spacious Deck
Designed for Long Days Outside
Open Living Area and Kitchen
Designed for Long Days Outside

72 Off Shore

4 bedrooms·3 baths
Hilton Head Island • South Carolina

$2,307.88 USD total for 3 nights

Oct 4 – 7, 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

After Dune Delight: Top Floor-HHI | 2 Bed/2 Bath image 1
After Dune Delight: Top Floor-HHI | 2 Bed/2 Bath image 2
After Dune Delight: Top Floor-HHI | 2 Bed/2 Bath image 3
Soak up the sun at the seasonally heated outdoor pool in Building 1 at Hilton Head Resort, located right next to The Beach Bear pool bar. It is the perfect spot to grab a bite or a cold drink after a swim!
After Dune Delight: Top Floor-HHI | 2 Bed/2 Bath image 5

After Dune Delight: Top Floor-HHI | 2 Bed/2 Bath

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$955.00 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)
Living Area
Private Patio with Grill
Queen's Grant Community Pool
Unlock Hilton Head – Guest-Only Deals on Excursions & Rentals
Your Stay with MyStay

701 Queen's Grant

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$820.32 USD total for 3 nights

Sep 29 – Oct 2, 2026

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

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

Spacious Deck for Dining and Lounging, Steps to Queen's Grant Pool
Spacious Living Room with Fresh Coastal Design & Vaulted Ceilings
1 of 5 Community Pools Steps from Villa!
Spacious Deck for Dining and Lounging, Steps to Queen's Grant Pool
Queen's Grant Aerial Views

789 Queen's Grant

2 bedrooms·2 baths
Hilton Head Island • South Carolina

$935.64 USD total for 3 nights

Oct 13 – 16, 2026

Beautiful, pet friendly 3 bedroom villa
Beautiful, pet friendly 3 bedroom villa
Beautiful, pet friendly 3 bedroom villa
Beautiful, pet friendly 3 bedroom villa
Beautiful, pet friendly 3 bedroom villa

Beautiful, pet friendly 3 bedroom villa

3 bedrooms·2½ baths
Hilton Head Island • South Carolina

$630.00 USD total for 3 nights

Oct 17 – 20, 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 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