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

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

Sep 29 – Oct 2, 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

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 29 – Oct 3, 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 29 – Oct 3, 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

$794.38 USD total for 3 nights

Sep 29 – Oct 2, 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 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
Living room

91 Sandcastle Court

5 bedrooms·5 baths
Hilton Head Island • South Carolina
5(44 reviews)

$3,087.07 USD total for 3 nights

Sep 29 – Oct 2, 2026

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

Family Room
Exterior Front
Kitchen
Kitchen
Beverage Area

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 29 – Oct 3, 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)
$199 – $350/ night(excl. fees & taxes)
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

Front of house
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

5 Sandy Beach Trail-4th row from the beach
Steps From The Beach! A few minute walk to beach access!
Main Level King Bedroom, fresh duvet cover, smart TV, private bathroom
Cozy Queen Bedroom on Main level w/ fresh duvet cover, smart TV and private bath
5 Sandy Beach Trail

5 Sandy Beach Trail

6 bedrooms·6½ baths
Hilton Head Island • South Carolina
5(8 reviews)

$4,367.87 USD total for 3 nights

Oct 4 – 7, 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

A Walk to Remember on Hilton Head
Outfitters bike rentals
Hilton Head Outfitters
Hilton Head Outfitters
Entrance to the Beach from The Dunes House access

A Walk to Remember on Hilton Head

3 bedrooms·2½ baths
Hilton Head Island • South Carolina
5(79 reviews)

$1,176.60 USD total for 3 nights

Sep 29 – Oct 2, 2026

Beach, Please! - HHI Escape
Beach, Please! - HHI Escape
Beach, Please! - HHI Escape
Beach, Please! - HHI Escape
Beach, Please! - HHI Escape

Beach, Please! - HHI Escape

2 bedrooms·1½ baths
Hilton Head Island • South Carolina
5(4 reviews)

$1,186.50 USD total for 3 nights

Sep 30 – Oct 3, 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

LR to kitchen
Master Bedroom
bedroom 2
dining room
Kitchen into LR

Cozy Coastal Chic

2 bedrooms·2 baths
Hilton Head Island • South Carolina
4.94(113 reviews)

$908.20 USD total for 3 nights

Sep 29 – Oct 2, 2026