Location

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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

Sep 22 – 26, 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)

$4,454.25 USD total for 5 nights

Sep 26 – Oct 1, 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

$2,345.49 USD total for 3 nights

Sep 25 – 28, 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

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

Sep 22 – 26, 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

$275/ night(excl. fees & taxes)

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

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

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

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

Sep 22 – 25, 2026

15 Crabline

8 bedrooms·6½ baths

Hilton Head Island • South Carolina

4.88(34 reviews)

$3,219.00 USD total for 3 nights

Sep 25 – 28, 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 25 – 28, 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

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

$3,600.03 USD total for 4 nights

Sep 22 – 26, 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

Sep 27 – 30, 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)

$1,420.00 USD total for 3 nights

Sep 22 – 25, 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

91 Sandcastle Court

5 bedrooms·5 baths

Hilton Head Island • South Carolina

5(44 reviews)

$3,087.07 USD total for 3 nights

Sep 22 – 25, 2026

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 22 – 26, 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

$955.69 USD total for 3 nights

Oct 4 – 7, 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

The living room has a smart tv and cable with its own sliding door giving access to the deck.

Blue Sky Villa:Queens Grant, 3bd, 2.5ba, Pets Ok

Master bedroom on the first floor with a king size bed, smart tv and cable box with access to its own master bathroom.

The master bath next to the master bedroom with double sink.

Fully stocked kitchen with microwave, dishwasher, electric range, refrigerator and washer and dryer.

Blue Sky Villa:Queens Grant, 3bd, 2.5ba, Pets Ok

3 bedrooms·2½ baths

Hilton Head Island • South Carolina

4.87(147 reviews)

$1,031.40 USD total for 3 nights

Sep 27 – 30, 2026

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