Location

Dates

Guests

Vacation rentals in Hilton Head Island, South Carolina, United States

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 28 – Oct 2, 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 28 – Oct 5, 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 28 – Oct 1, 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

Oct 1 – 4, 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)

$572.22 USD total for 3 nights

Sep 28 – Oct 1, 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 28 – Oct 2, 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 28 – Oct 1, 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 28 – Oct 1, 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 28 – Oct 1, 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)

$2,653.93 USD total for 3 nights

Sep 28 – Oct 1, 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)

$2,791.65 USD total for 3 nights

Sep 28 – Oct 1, 2026

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 28 – Oct 1, 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)

$1,086.40 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

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 28 – Oct 1, 2026

Kitchen into LR

Cozy Coastal Chic

2 bedrooms·2 baths

Hilton Head Island • South Carolina

4.94(113 reviews)

$934.60 USD total for 3 nights

Sep 28 – Oct 1, 2026

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)

$898.29 USD total for 3 nights

Oct 17 – 20, 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 28 – Oct 1, 2026

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)

$664.35 USD total for 3 nights

Sep 28 – Oct 1, 2026