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

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)
$425 – $745/ night(excl. fees & taxes)
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

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 28 – 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
15 Crabline
15 Crabline
15 Crabline
15 Crabline

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

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

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
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 22 – 25, 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)

$3,028.00 USD total for 3 nights

Sep 23 – 26, 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

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)

$2,990.34 USD total for 3 nights

Sep 22 – 25, 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

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

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)

$972.00 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)

$883.64 USD total for 3 nights

Oct 17 – 20, 2026

Dog Friendly Stones Throw from Folly Field Beach
Dog Friendly Stones Throw from Folly Field Beach
Dog Friendly Stones Throw from Folly Field Beach image 2
Dog Friendly Stones Throw from Folly Field Beach image 17
Dog Friendly Stones Throw from Folly Field Beach image 3

Dog Friendly Stones Throw from Folly Field Beach

2 bedrooms·2½ baths
Hilton Head Island • South Carolina

$825.00 USD total for 3 nights

Sep 22 – 25, 2026

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

View from private deck
103 Carolina Club Shipyard Planation
View of front of house
View of back of house
Aerial view of amenities

103 Carolina Club Shipyard Planation

3 bedrooms·3 baths
Hilton Head Island • South Carolina
$140 – $157/ night(excl. fees & taxes)