Location

Dates

Guests

Vacation rentals in Hilton Head Island

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

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

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)

$692.10 USD total for 3 nights

Sep 26 – 29, 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

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

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

Beachside Resort - Family Comfort 4 U - 2-Bedroom image 9

Fully Stocked Kitchen

Beachside Resort - Family Comfort 4 U - 2-Bedroom image 5

Beachside Resort - Family Comfort 4 U - 2-Bedroom image 10

Beachside Resort - Family Comfort 4 U - 2-Bedroom image 7

Beachside Resort - Family Comfort 4 U - 2-Bedroom

2 bedrooms·2 baths

Hilton Head Island • South Carolina

4.93(14 reviews)

$880.80 USD total for 3 nights

Sep 22 – 25, 2026

3 bdr, Easy Walk to Beach, Pickleball Tennis, Golf

3 bdr, Easy Walk to Beach, Pickleball Tennis, Golf

3 bdr, Easy Walk to Beach, Pickleball Tennis, Golf

3 bdr, Easy Walk to Beach, Pickleball Tennis, Golf

3 bdr, Easy Walk to Beach, Pickleball Tennis, Golf

3 bdr, Easy Walk to Beach, Pickleball Tennis, Golf

3 bedrooms·2½ baths

Hilton Head Island • South Carolina

4.82(11 reviews)

$196 – $813/ night(excl. fees & taxes)

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 22 – 25, 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

Sep 22 – 27, 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 22 – 25, 2026

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

Welcome to The Carolina Condo! A newly remodeled beach boutique-style condo.

Follow the boardwalk through the dunes and let the day slow down. Your toes-in-the-sand moment is just ahead. Our condo is just steps to the beach!

Check out the ocean view! Breath in the fresh ocean air and take it all in from the second floor balcony!

A bright, coastal kitchen with quartz countertops, stainless steel appliances, and everything you need for easy vacation meals.

Brand New Lux Condo - Ocean View! Steps to Beach!

1 bedroom·1 bath

Hilton Head Island • South Carolina

$141 – $768/ night(excl. fees & taxes)

Bar (on property)

Bar (on property)

Calming lagoon view 2 BR condo on Hilton Head Island.

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(6 reviews)

$778.85 USD total for 3 nights

Sep 22 – 25, 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 25 – 28, 2026

Welcome to the Isle of View with Ocean views and sunrises directly from your balcony.
The morning sun is AMAZING and you will find yourself relaxed in minutes in this bright and airy space.

Nap on the couch or the recliner after watching the sunrise from your balcony....decisions are tough on vacation!

An extra window and large sliders make for a bright sun filled living area.

Window provides extra light in fully equipped kitchen with several additional small appliances including your own ice maker.

Margarita maker and ice machine in Villa will have you relaxing in no time.

Beautiful Oceanfront Villa with Amazing Sunrises

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.85(169 reviews)

$145 – $250/ night(excl. fees & taxes)

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)

$730.95 USD total for 3 nights

Sep 22 – 25, 2026

Wireless charging on every end table! Smart TV and new furniture added march 2021.

HHBT c258

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.83(188 reviews)

$610.00 USD total for 3 nights

Sep 22 – 25, 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

Picture yourself having your morning coffee on our balcony!

This is a beautiful stroll to the beach. Fiddler's also has 2 private beach entrances.

Taken at Folly Field Beach at sunrise. I love seeing dolphins from the shore!

Our kitchen is stocked with a Starter supply of kitchen products: Paper towels, dish soap, dishwasher tabs, etc.

Our newly renovated kitchen! New appliances, quartz countertops, frosted glass backsplash!

Fiddler's Escape-Chilled Pool, Walk to Beach

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(108 reviews)

$852.50 USD total for 3 nights

Sep 22 – 25, 2026

Beautiful sunrise on Folly Field Beach, just 2 blocks from the condo. Only about 5 min walk to the ocean!

Miles and miles of white sandy beaches.

Wow Factor! Folly Field Beach Renovated Cute Clean

Welcome to your vacation! Beach, pools, tennis, hot tub, clubhouse, barbeque grills, picnic tables.... all for you to enjoy.

Just a 5 minute walk to Folly Field Beach! Beach chairs, Beach buggy included

Wow Factor! Folly Field Beach Renovated Cute Clean

2 bedrooms·2 baths

Hilton Head Island • South Carolina

4.67(51 reviews)

$642.85 USD total for 3 nights

Sep 22 – 25, 2026

Coastal Cabana-10 min walk to Private Beach Access

Coastal Cabana-10 min walk to Private Beach Access

Coastal Cabana-10 min walk to Private Beach Access

Coastal Cabana-10 min walk to Private Beach Access

Coastal Cabana-10 min walk to Private Beach Access

Coastal Cabana-10 min walk to Private Beach Access

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(7 reviews)

$910.02 USD total for 3 nights

Sep 22 – 25, 2026