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 22 – 26, 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 22 – 25, 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 22 – 25, 2026

Living room
Kitchen
Kitchen
Kitchen and dining
Dining

Lovely 2 BR condo~resort amenities~beachside

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.95(19 reviews)

$816.20 USD total for 3 nights

Sep 22 – 25, 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 28 – Oct 2, 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 27 – Oct 1, 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

$1,021.77 USD $977.71 USD total for 3 nights

Sep 22 – 25, 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)

$980.80 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

Sep 28 – Oct 1, 2026

Beachside Resort - Family Comfort 4 U - 2-Bedroom image 9
Fully Stocked Kitchen
Beachside Resort - Family Comfort 4 U - 2-Bedroom image 5
Beachside Resort - Family Comfort 4 U - 2-Bedroom image 10
Beachside Resort - Family Comfort 4 U - 2-Bedroom image 7

Beachside Resort - Family Comfort 4 U - 2-Bedroom

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.93(14 reviews)

$880.80 USD total for 3 nights

Sep 22 – 25, 2026

3 bdr, Easy Walk to Beach, Pickleball Tennis, Golf
3 bdr, Easy Walk to Beach, Pickleball Tennis, Golf
3 bdr, Easy Walk to Beach, Pickleball Tennis, Golf
3 bdr, Easy Walk to Beach, Pickleball Tennis, Golf
3 bdr, Easy Walk to Beach, Pickleball Tennis, Golf

3 bdr, Easy Walk to Beach, Pickleball Tennis, Golf

3 bedrooms·2½ baths
Hilton Head Island • South Carolina
4.82(11 reviews)
$196 – $813/ night(excl. fees & taxes)
Sunny Sails-11 min walk to Private Beach Access image 1
Sunny Sails-11 min walk to Private Beach Access image 2
Sunny Sails-11 min walk to Private Beach Access image 3
Sunny Sails-11 min walk to Private Beach Access image 4
Sunny Sails-11 min walk to Private Beach Access image 5

Sunny Sails-11 min walk to Private Beach Access

2 bedrooms·2 baths
Hilton Head Island • South Carolina
5(6 reviews)

$883.64 USD total for 3 nights

Oct 17 – 20, 2026

Welcome to The Carolina Condo! A newly remodeled beach boutique-style condo.
Follow the boardwalk through the dunes and let the day slow down. Your toes-in-the-sand moment is just ahead. Our condo is just steps to the beach!
Check out the ocean view! Breath in the fresh ocean air and take it all in from the second floor balcony!
Bright and open living room with brand new 65" TCL Roku Smart TV. Stream your favorite shows or watch cable TV. Ocean views from the sofa!
A bright, coastal kitchen with quartz countertops, stainless steel appliances, and everything you need for easy vacation meals.

Brand New Lux Condo - Ocean View! Steps to Beach!

1 bedroom·1 bath
Hilton Head Island • South Carolina
$141 – $768/ night(excl. fees & taxes)
Welcome to the Isle of View with Ocean views and sunrises directly from your balcony. The morning sun is AMAZING and you will find yourself relaxed in minutes in this bright and airy space.
Nap on the couch or the recliner after watching the sunrise from your balcony....decisions are tough on vacation!
An extra window and large sliders make for a bright sun filled living area.
Window provides extra light in fully equipped kitchen with several additional small appliances including your own ice maker.
Margarita maker and ice machine in Villa will have you relaxing in no time.

Beautiful Oceanfront Villa with Amazing Sunrises

1 bedroom·1 bath
Hilton Head Island • South Carolina
4.85(169 reviews)
$145 – $250/ night(excl. fees & taxes)
Welcome to the Isle of View 2. The open floor plan is big enough for large families but has a comfortable, cozy feel throughout.
Kitchen stocked with everything you need including microwave, blender, toaster, croc pot, keurig and drip coffee maker. There is even an ice maker so you will never run out!
Kitchen stocked with everything you need including microwave, blender, toaster, croc pot, keurig and drip coffee maker. There is even an ice maker so you will never run out!
Kitchen provides everything from a Keurig Coffee maker to your own ice machine. Prefer drip coffee? We have that too!
Flat screen, smart tv with cable, board games, and puzzles will entertain you in living room and the comfy sleep sofa accommodates extra guests or larger families.

Isle of View 2- Large 2BR that sleeps 8

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.83(52 reviews)

$730.95 USD total for 3 nights

Sep 22 – 25, 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 22 – 25, 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 22 – 25, 2026

A romantic escape starts here. Slow mornings, coffee for two, sweeping ocean views and unforgettable sunrises—all from your private top-floor balcony. Sea La Vie is the kind of getaway that makes you slow down, reconnect and wish you’d stay longer!
Top-floor oceanview balcony with views of the Atlantic, fountain pond, and beach boardwalk. The perfect spot for sunrise coffee, evening cocktails, and salty ocean breezes.
Enjoy an open-concept living area with custom gallery walls, comfortable seating, and a charming dining space. Bright, airy, and thoughtfully designed, this room blends coastal elegance with modern comfort.
Start your day with coffee on the balcony in this top-floor retreat offering expansive views, in the coveted “Y” positioning, the “sweet spot” overlooking the ocean, tranquil fountain, and private boardwalk The stay you wished you booked longer.
The bright, open layout with stunning Grasscloth wallpaper flows seamlessly from bedroom to living spaces, leading toward the balcony and expansive ocean views beyond.

Luxury OCEANVIEW at Oceanfront Resort - Romantic Escape

1 bedroom·1 bath
Hilton Head Island • South Carolina
5(61 reviews)

$1,170.19 USD total for 3 nights

Sep 22 – 25, 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
5(136 reviews)

$503.94 USD total for 3 nights

Sep 27 – 30, 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)

$1,625.90 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)
$449/ night(excl. fees & taxes)
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
$290/ night(excl. fees & taxes)
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 6 – 13, 2026