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

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

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

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

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)
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

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

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

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

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

Palmetto Dunes Golf and Tennis Villa
Palmetto Dunes Golf and Tennis Villa
Palmetto Dunes Golf and Tennis Villa
Palmetto Dunes Golf and Tennis Villa
Palmetto Dunes Golf and Tennis Villa

Palmetto Dunes Golf and Tennis Villa

2 bedrooms·3 baths
Hilton Head Island • South Carolina
5(9 reviews)

$1,595.00 USD total for 5 nights

Oct 31 – Nov 5, 2026

Stones Throw from the beach
Stones Throw from the beach
Stones Throw from the beach
Stones Throw from the beach
Stones Throw from the beach

Stones Throw from the beach

2 bedrooms·1½ baths
Hilton Head Island • South Carolina
4.89(46 reviews)

$700.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

Ocean front pool. There are two pools, including a kiddie pool. Beach front bar next to this pool.
Path to the beach a two minute walk. Our condo is fully renovated. Hilton Head Beach and Tennis Resort is a trolley stop as well!
Hallway looking at the door to outside of the condo
Triple bunk bed. Full size bed on the top. And two twin beds on the bottom.
TV in bunk room

Beach and Tennis Resort. Family Friendly

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(46 reviews)

$820.00 USD total for 3 nights

Sep 29 – Oct 2, 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

Beautiful sunrise on Folly Field Beach, just 2 blocks from the condo. Only about 5 min walk to the ocean!
Miles and miles of white sandy beaches.
Wow Factor! Folly Field Beach Renovated Cute Clean
Welcome to your vacation! Beach, pools, tennis, hot tub, clubhouse, barbeque grills, picnic tables.... all for you to enjoy.
Just a 5 minute walk to Folly Field Beach! Beach chairs, Beach buggy included

Wow Factor! Folly Field Beach Renovated Cute Clean

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.67(51 reviews)

$642.85 USD total for 3 nights

Sep 29 – Oct 2, 2026

Coastal Cabana-10 min walk to Private Beach Access
Coastal Cabana-10 min walk to Private Beach Access
Coastal Cabana-10 min walk to Private Beach Access
Coastal Cabana-10 min walk to Private Beach Access
Coastal Cabana-10 min walk to Private Beach Access

Coastal Cabana-10 min walk to Private Beach Access

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(7 reviews)

$797.68 USD total for 3 nights

Sep 29 – Oct 2, 2026

Welcome to "Tygers On The Beach", providing you with everything you need to relax and unwind on Hilton Head Island!
Relax on the comfy brand new living room set while you stream your favorite shows on the 65” TV. Cable TV is provided on this TV only, you'll need to bring your streaming passwords to sign into th
Pamper yourself using the makeup table with touch control lighting. For your convenience, USB charging ports are on the lamps in both bedrooms.
Picture yourself in this Olympic size heated/ cooled pool, enjoying the provided beach towels. Pools are open March 1- Nov. 1.
Relax or nap on this super comfortable Brand New recliner. Purchased November 2023.

Fiddler's Cove 13B 1st Floor, Heated pools, W/D

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.97(137 reviews)

$503.94 USD total for 3 nights

Oct 5 – 8, 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