Location

Dates

Guests

Vacation rentals in Hilton Head Island

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

Oct 20 – 23, 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)

$2,406.40 USD total for 3 nights

Oct 28 – 31, 2026

Welcome to 3 Lookout with amazing outdoor spaces including large swimming pool and spillover spa

Who can resist the lounge chairs for sunbathing and refreshing dips in the pool

Hot tub can be heated for no additional charge

Great home for large family gatherings that allows six cars max.

Lots of space to spread out in this 7 Bedroom 7 Bath home only 1/4 mile to Beach

Palmetto Dunes, 5 mins to Beach, Sleep 23 in beds

7 bedrooms·6½ baths

Hilton Head Island • South Carolina

5(186 reviews)

$3,080.25 USD $2,730.60 USD total for 3 nights

Oct 20 – 23, 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

May 1 – 5, 2027

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

$854.16 USD total for 3 nights

Nov 16 – 19, 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 25 – 28, 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)

$885.10 USD total for 3 nights

Oct 25 – 28, 2026

Bright open dining space with full kitchen, bar seating, and in-unit laundry

Pet-Friendly 3BR Villa Walk to Beach, Golf, Tennis

Pet-Friendly 3BR Villa Walk to Beach, Golf, Tennis

Pet-Friendly 3BR Villa Walk to Beach, Golf, Tennis

Pet-Friendly 3BR Villa Walk to Beach, Golf, Tennis

Pet-Friendly 3BR Villa Walk to Beach, Golf, Tennis

3 bedrooms·2½ baths

Hilton Head Island • South Carolina

$986.25 USD total for 3 nights

Nov 16 – 19, 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)

$2,673.99 USD total for 3 nights

Oct 20 – 23, 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)

$3,477.22 USD total for 3 nights

Oct 31 – Nov 3, 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

Nov 8 – 11, 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 20 – 23, 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)

$921.40 USD total for 3 nights

Oct 20 – 23, 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)

$550.04 USD total for 3 nights

Dec 3 – 6, 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)

$1,143.30 USD total for 3 nights

Oct 20 – 23, 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

Oct 20 – 23, 2026

Private shaded deck with outdoor dining, grill, and lush tropical views

Private villa entrance with landscaped walkway and welcoming covered entry

Bright coastal entryway with warm wood stairs and charming beach decor

Bright coastal entryway with natural light, wood stairs, and charming decor

Bright, airy entryway with vaulted ceilings and inviting coastal style

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

3 bedrooms·2½ baths

Hilton Head Island • South Carolina

5(1 review)

$821.37 USD total for 3 nights

Oct 26 – 29, 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

Oct 20 – 23, 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

Oct 22 – 25, 2026

Kitchen into LR

Cozy Coastal Chic

2 bedrooms·2 baths

Hilton Head Island • South Carolina

4.94(113 reviews)

$774.00 USD total for 3 nights

Nov 14 – 17, 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(7 reviews)

$854.16 USD total for 3 nights

Oct 25 – 28, 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

$663.30 USD total for 3 nights

Oct 20 – 23, 2026

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

Oct 20 – 23, 2026