Location

Dates

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Vacation rentals in Hilton Head Island

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

Oct 20 – 24, 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

Oct 20 – 27, 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

4.91(76 reviews)

$4,085.55 USD total for 5 nights

Oct 24 – 29, 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 20 – 23, 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

Oct 20 – 23, 2026

Private Indoor Pool with Deck Access

Chef-Ready Kitchen with Modern Amenities & Breakfast Island

Serene Primary Suite Overlooking the Private Indoor Pool

Panoramic Water Views from the Heart of the Home

Private Indoor Pool (Can Be Heated) – Year-Round Fun

4 Slack Tide

4 bedrooms·5 baths

Hilton Head Island • South Carolina

$3,274.01 USD total for 4 nights

Oct 20 – 24, 2026

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

Oct 20 – 25, 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

Oct 20 – 23, 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

Oct 20 – 23, 2026

Kitchen and 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

Nov 1 – 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(153 reviews)

$985.00 USD total for 3 nights

Oct 20 – 23, 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- 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)

$109 – $587/ night(excl. fees & taxes)

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

Oct 20 – 24, 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

Oct 20 – 24, 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 20 – 23, 2026

15 Crabline

8 bedrooms·6½ baths

Hilton Head Island • South Carolina

4.88(34 reviews)

$3,219.00 USD total for 3 nights

Oct 20 – 23, 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

4(1 review)

$2,734.50 USD total for 3 nights

Oct 20 – 23, 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

$845.44 USD total for 3 nights

Oct 23 – 26, 2026

NEW, 2 bedroom; 2.5 Bath;WALK To BEACH

NEW, 4Bedroom; 4.5 Bath;WALK To BEACH image 3

NEW, 2 bedroom; 2.5 Bath;WALK To BEACH

NEW, 2 bedroom; 2.5 Bath;WALK To BEACH

NEW, 2 bedroom; 2.5 Bath;WALK To BEACH

NEW, 2 bedroom; 2.5 Bath;WALK To BEACH

4 bedrooms·4 baths

Hilton Head Island • South Carolina

5(7 reviews)

$1,090.00 USD total for 3 nights

Oct 25 – 28, 2026

1 bedroom apartment; WALK to BEACH

1 bedroom apartment; WALK to BEACH

1 bedroom apartment; WALK to BEACH

1 bedroom apartment; WALK to BEACH

1 bedroom apartment; WALK to BEACH

1 bedroom apartment; WALK to BEACH

1 bedroom·1 bath

Hilton Head Island • South Carolina

$780.00 USD total for 3 nights

Oct 25 – 28, 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 Go-To Palmetto Dunes Home for Space, Golf & Lagoon Views, and Fun

Open, Bright, and Easy to Be Together

Game Night Headquarters: Pool Table, Ping Pong & Grab-and-Go Beach Gear

Kitchen with Breakfast Nook, Big Counter & Easy Pool Access

2 High Water | A Big, Bright Palmetto Dunes Getaway Made for Together Time

2 High Water

5 bedrooms·5 baths

Hilton Head Island • South Carolina

$2,832.90 USD total for 3 nights

Oct 20 – 23, 2026

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

$816.55 USD total for 3 nights

Oct 25 – 28, 2026

Welcome to the Carolina Breeze Bungalow! Be(ach) our guest and enjoy all that this little cottage near the sea has to offer!

Charming 3BR / 2 bath beach bungalow with hot tub

Coastal-vibe feels throughout!

Fully-equipped kitchen with everything needed for cooking in. Ample glassware, flatware, cookware, serving pieces...all that's needed for a dishing up a delicious meal!

Start the morning with a cup of coffee via drip, Keurig or French press!

Charming 3BR / 2 bath beach bungalow with hot tub

3 bedrooms·2 baths

Hilton Head Island • South Carolina

5(47 reviews)

$1,062.00 USD total for 3 nights

Oct 26 – 29, 2026