Location

Dates

Guests

Vacation rentals in Hilton Head Island

View from the living room swivel chair.

Living Room with new La-Z-Boy sofa & Love Seat

Dining table with 6 chairs

Living Room with new furnishings.

Main Suite with King Bed.

Villamare 3328, 5 stars, Ocean views

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(6 reviews)

$4,145.33 USD $3,369.88 USD total for 7 nights

Oct 24 – 31, 2026

Swimming poor 6-3 feet
May heat w/additional charge

“Dune” It Right

In private neighborhood w/ lots of greenery

“Dune” It Right

“Dune” It Right

“Dune” It Right

5 bedrooms·5½ baths

Hilton Head Island • South Carolina

5(100 reviews)

$1,097.00 USD total for 3 nights

Nov 1 – 4, 2026

Family Pool and Hot Tub

Serenity Pool and Hot Tub

3125 Villamare - Oceanfront

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(62 reviews)

$1,726.80 USD $1,420.44 USD total for 3 nights

Oct 31 – Nov 3, 2026

3522 Villamare

2 bedrooms·2 baths

Hilton Head Island • South Carolina

$2,600.00 USD total for 3 nights

Oct 20 – 23, 2026

Oceanfront Villamare 3524!

Oceanfront Villamare 3524!

Oceanfront Villamare 3524!

Oceanfront Villamare 3524!

Oceanfront Villamare 3524!

Oceanfront Villamare 3524!

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(36 reviews)

$5,610.00 USD total for 7 nights

Mar 13 – 20, 2027

Cozy Casual Beach Retreat

Cozy Casual Beach Retreat

Cozy Casual Beach Retreat

3 bedrooms·3 baths

Hilton Head Island • South Carolina

$2,500.00 USD total for 5 nights

Oct 20 – 25, 2026

Kitchen and dining

Kitchen and living room

Kitchen and dining

Living room with 65 inch smart TV

3523 VILLAMARE - OCEANFRONT-STUNNING!

2 bedrooms·2 baths

Hilton Head Island • South Carolina

$2,832.50 USD total for 3 nights

Oct 20 – 23, 2026

Lagoon views with water on 3 sides of back/side yard

Relaxing front porch with lots of privacy

Incredible views from the screened in porch

Private pool with incredible views and lots of privacy! (Heat additional)

Large screened in rear porch to enjoy the incredible views

"After Dune Delight"

5 bedrooms·4 baths

Hilton Head Island • South Carolina

4.91(87 reviews)

$10,086.00 USD total for 7 nights

Nov 19 – 26, 2026

View from balcony

6205 Hampton Place

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(11 reviews)

$1,610.00 USD total for 4 nights

Oct 20 – 24, 2026

4Bd/3Ba, Beach/Pool/Pickleball/Tennis/Pet Friendly

4Bd/3Ba, Beach/Pool/Pickleball/Tennis/Pet Friendly

4Bd/3Ba, Beach/Pool/Pickleball/Tennis/Pet Friendly

4Bd/3Ba, Beach/Pool/Pickleball/Tennis/Pet Friendly

4Bd/3Ba, Beach/Pool/Pickleball/Tennis/Pet Friendly

4Bd/3Ba, Beach/Pool/Pickleball/Tennis/Pet Friendly

4 bedrooms·1 bath

Hilton Head Island • South Carolina

5(4 reviews)

$2,781.00 USD total for 7 nights

Oct 31 – Nov 7, 2026

Spacious | Family Friendly | 0.8 Miles to Beach

Spacious | Family Friendly | 0.8 Miles to Beach

Spacious | Family Friendly | 0.8 Miles to Beach

Spacious | Family Friendly | 0.8 Miles to Beach

Spacious | Family Friendly | 0.8 Miles to Beach

Spacious | Family Friendly | 0.8 Miles to Beach

2 bedrooms·2½ baths

Hilton Head Island • South Carolina

4.67(18 reviews)

$1,610.00 USD total for 7 nights

Oct 20 – 27, 2026

Newly renovated condo!

Just renovated kitchen!!

87 Ocean Breeze, Walk to the Beach, Tennis, 3 Pools, Just renovated!!

87 Ocean Breeze, Walk to the Beach, Tennis, 3 Pools, Just renovated!!

3 bedrooms·3 baths

Hilton Head Island • South Carolina

$986.50 USD total for 3 nights

Oct 20 – 23, 2026

Exterior detail

Private kitchen

Beautiful Palmetto Dunes 3 Bedroom pet friendly villa.

3 bedrooms·2 baths

Hilton Head Island • South Carolina

$959.00 USD total for 3 nights

Oct 25 – 28, 2026

Splash of Water

Splash of Water

Lagoon and golf course view

Large deck located off of living room

Lagoon and golf course view

Splash of Water

3 bedrooms·3 baths

Hilton Head Island • South Carolina

5(1 review)

$1,275.00 USD total for 3 nights

Oct 20 – 23, 2026

Dining/Living Room

The Greens at Shipyard - 9-min. walk to the beach

2 bedrooms·2½ baths

Hilton Head Island • South Carolina

5(66 reviews)

$1,304.71 USD total for 3 nights

Dec 1 – 4, 2026

Charming coastal villa,8 min walk to the Shipyard image 35

THIS AWAITS YOU......

Beautiful pool makeover March 2026
A two minute walk from our villa, enjoy! 🌞🌴

Charming coastal villa,8 min walk to the Shipyard image 45

Beachwalk Beauty

2 bedrooms·2 baths

Hilton Head Island • South Carolina

4.99(110 reviews)

$1,847.80 USD total for 7 nights

Oct 24 – 31, 2026

Upon entering, you are welcomed into our newly renovated kitchen and open-concept first floor. Enjoy the sunny atrium with built-in window seats. Quartz countertops, full-size pantry, and upgraded cabinets adorn this fully appointed-kitchen.

Beachwalk 165 is a beautiful villa located in Shipyard, Hilton Head Island. Renovated in 2025, the villa features an open concept first floor and plenty of space to relax year-round.

Upon entering, you are welcomed into our newly renovated kitchen and open-concept first floor. Enjoy the sunny atrium with built-in window seats. Quartz countertops, full-size pantry, and upgraded cabinets adorn this fully appointed-kitchen.

This sunny atrium is perfect for enjoying a cup of coffee, a good book or a board game.

The dining room features a new table with seating for six. Beyond dining, the room is perfect for games and family fun. Comfortable seating for three is available at the kitchen island.

Beachwalk 165, Shipyard/Guest Favorite

2 bedrooms·2½ baths

Hilton Head Island • South Carolina

$1,224.00 USD total for 4 nights

Oct 27 – 31, 2026

The Tidal Cottage I Beach Access + Pools

The Tidal Cottage I Beach Access + Pools

The Tidal Cottage I Beach Access + Pools

The Tidal Cottage I Beach Access + Pools

The Tidal Cottage I Beach Access + Pools

The Tidal Cottage I Beach Access + Pools

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(4 reviews)

$217/ night(excl. fees & taxes)

Carolina Room: A Sunlit Sanctuary Overlooking the Water

Deck with Lagoon Access: Tranquil Waters Await – Relax, Unwind, Repeat

Kayak Rentals (Hilton Head Outfitters): Adventure Awaits – Rent Kayaks Just Up the Street

Dining Area: Gather, Savor, and Create Lasting Memories

Pool Area: Swim, Soak & Splash – Fun for Everyone

7649 Huntington Villa

3 bedrooms·4 baths

Hilton Head Island • South Carolina

$2,521.16 USD total for 4 nights

Apr 3 – 7, 2027

Premium Ocean Views

Bright Modern Living Room with Oceanview Balcony

Stunning View from Your Private Balcony

Bright Modern Living Room with Oceanview Balcony

Spacious Primary Suite with Plush Bedding

4405 Windsor Court North

2 bedrooms·2 baths

Hilton Head Island • South Carolina

$1,267.81 USD total for 3 nights

Oct 20 – 23, 2026

Villa Evian – 2BR Shipyard, Near Beach & Golf

Villa Evian – 2BR Shipyard, Near Beach & Golf

Villa Evian – 2BR Shipyard, Near Beach & Golf

Villa Evian – 2BR Shipyard, Near Beach & Golf

Villa Evian – 2BR Shipyard, Near Beach & Golf

Villa Evian – 2BR Shipyard, Near Beach & Golf

2 bedrooms·2½ baths

Hilton Head Island • South Carolina

$1,125.00 USD total for 3 nights

Apr 1 – 4, 2027

Enjoy and relax in front of the tv or enjoy the view of the golf course.

Sand Sun & Beach

Sand Sun & Beach

Great space to relax and play games.

Grab some breakfast before your day at the beach.

Sand Sun & Beach

2 bedrooms·2½ baths

Hilton Head Island • South Carolina

4.99(84 reviews)

$888.00 USD total for 3 nights

Sep 30 – Oct 3, 2027

Fully renovated kitchen - end of Dec 2025

All new appliances

Island with 3 seats

Air fryer oven and outside water dispenser

Bench seat to take off shoes and open staircase

Hilton Head Island, SC - Shipyard Plantation, The Greens

2 bedrooms·2½ baths

Hilton Head Island • South Carolina

4.9(269 reviews)

$1,692.00 USD total for 7 nights

Oct 20 – 27, 2026

Walk to Beach | 3 Pools + Hot Tub image 1

Walk to Beach | 3 Pools + Hot Tub image 2

Pool 2, located toward the beach

Main Pool centrally located

Walk to Beach | 3 Pools + Hot Tub image 5

Walk to Beach | 3 Pools + Hot Tub

2 bedrooms·2 baths

Hilton Head Island • South Carolina

4.58(19 reviews)

$590.00 USD total for 3 nights

Oct 25 – 28, 2026