Location

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Vacation rentals in Hilton Head Island, SC, USA

Coastal Soul-Gorgeous Direct OceanFront!

Coastal Soul-Gorgeous Direct OceanFront!

Coastal Soul-Gorgeous Direct OceanFront!

Coastal Soul-Gorgeous Direct OceanFront!

Coastal Soul-Gorgeous Direct OceanFront!

Coastal Soul-Gorgeous Direct OceanFront!

1 bedroom·1 bath

Hilton Head Island • South Carolina

5(73 reviews)

$1,807.50 USD total for 4 nights

Jun 2 – 6, 2027

A serene getaway at the beach

Roku smart TV in the Living Room

All appliances, utensils and cookware you will need to prepare meals.

Comfortable Queen bed in the primary bedroom

Smart TV for your private viewing

HHI Hidden Dunes

2 bedrooms·1 bath

Hilton Head Island • South Carolina

5(146 reviews)

$483.00 USD total for 3 nights

Nov 2 – 5, 2026

Sea Pines Serenity

Sea Pines Serenity

Sea Pines Serenity

Sea Pines Serenity

Sea Pines Serenity

Sea Pines Serenity

3 bedrooms·2 baths

Hilton Head Island • South Carolina

5(4 reviews)

$2,073.00 USD total for 4 nights

Oct 28 – Nov 1, 2026

Seascape Villas 3247 - Deck - The outside deck is a great place to relax and enjoy the wonderful view.

Seascape Villas 3247 - Deck - The outside deck is a great place to relax and enjoy the wonderful view.

Seascape Villas 3247 - Living Area - The Living Room Area has sliding door access to the beautiful wooded area deck with grill. Upscale furnishings and a flat screen television complete the space.

Seascape Villas 3247- Living Area - The Living Room Area and dining room.

Seascape Villas 3247 - Living Area - View of living room and kitchen with passthrough.

All-New HHI Seascape Villa | Walk to Beach & Pools

2 bedrooms·2 baths

Hilton Head Island • South Carolina

4.92(13 reviews)

$872.50 USD total for 3 nights

Oct 28 – 31, 2026

Just Steps to the Pool, Minutes to the Beach

3019 Seascape

2 bedrooms·2 baths

Hilton Head Island • South Carolina

$806.39 USD total for 3 nights

Oct 27 – 30, 2026

Seascape Escape

Seascape Escape

Seascape Escape

Seascape Escape

Seascape Escape

Seascape Escape

3 bedrooms·2 baths

Hilton Head Island • South Carolina

4.65(17 reviews)

$1,340.00 USD total for 3 nights

Oct 28 – 31, 2026

Bright and Airy Living Area with Private Deck Access

Scenic Lagoon-View Deck with Private Grill & Pool Path Access

Scenic Lagoon-View Deck with Private Grill & Pool Path Access

3232 Seascape

2 bedrooms·3 baths

Hilton Head Island • South Carolina

$115 – $359/ night(excl. fees & taxes)

Small density complex with 2 assigned parking spots right across from beach!

Fully equipped kitchen with table for 2

Granite countertops

Light and bright living area with neutral furniture

Spacious King Master with Roku TV

Steel City Escape - Ocean Gate next to Sea Pines

2 bedrooms·2½ baths

Hilton Head Island • South Carolina

5(50 reviews)

$1,201.02 USD total for 3 nights

Nov 21 – 24, 2026

⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐

⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐

⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐

⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐

⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐

⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐

1 bedroom·1 bath

Hilton Head Island • South Carolina

4.91(223 reviews)

$797.55 USD total for 3 nights

Oct 29 – Nov 1, 2026

Ocean views, morning to sunset

Relax, recharge, repeat

Heated pool, year-round vibes

Front-row seat to the Atlantic

Heated pool, year-round vibes

408 Ocean Dunes

1 bedroom·1 bath

Hilton Head Island • South Carolina

$816.80 USD total for 3 nights

Oct 31 – Nov 3, 2026

Living Room/Dining

Living Room/Dining

Living Room/Dining/Kitchen

309 Ocean Dunes Villas

2 bedrooms·2 baths

Hilton Head Island • South Carolina

4.81(190 reviews)

$2,651.50 USD total for 7 nights

Nov 9 – 16, 2026

Hilton Head Sea Pines Getaway

Hilton Head Sea Pines Getaway

Foyer/entry way

Hilton Head Sea Pines Getaway

Hilton Head Sea Pines Getaway

5 bedrooms·3½ baths

Hilton Head Island • South Carolina

4.85(82 reviews)

$1,813.26 USD total for 3 nights

Oct 29 – Nov 1, 2026

Bayberry Breeze - Steps to the Shore - Pool/Hottub

Bayberry Breeze - Steps to the Shore - Pool/Hottub

Main living area

Bayberry Breeze - Steps to the Shore - Pool/Hottub

Bayberry Breeze - Steps to the Shore - Pool/Hottub

Bayberry Breeze - Steps to the Shore - Pool/Hottub

5 bedrooms·4 baths

Hilton Head Island • South Carolina

$1,688.65 USD total for 3 nights

Nov 2 – 5, 2026

Beach path to ocean

Great Room To Kithchen

Dining to Outside

Pet Friendly Luxury Near Ocean Home

3 bedrooms·2 baths

Hilton Head Island • South Carolina

4.84(56 reviews)

$4,075.00 USD total for 7 nights

Oct 28 – Nov 4, 2026

Sea Pines · Walk to Beach · Lagoon Deck · 3BR image 1

Sea Pines · Walk to Beach · Lagoon Deck · 3BR image 3

Sea Pines · Walk to Beach · Lagoon Deck · 3BR image 4

Sea Pines · Walk to Beach · Lagoon Deck · 3BR

Sea Pines · Walk to Beach · Lagoon Deck · 3BR

Sea Pines · Walk to Beach · Lagoon Deck · 3BR

3 bedrooms·2 baths

Hilton Head Island • South Carolina

5(9 reviews)

$1,240.00 USD total for 3 nights

Nov 1 – 4, 2026

Sun-Drenched Pool Terrace With Endless Ocean Breezes

35 Ruddy Turnstone - Oceanfront Estate Framed by Palmettos & Ancient Oaks

Bird’s-Eye View of Your Secluded Beach Walkway

Your Private Path to the Shore

Unlock Hilton Head – Guest-Only Deals on Excursions & Rentals

35 Ruddy Turnstone

5 bedrooms·7 baths

Hilton Head Island • South Carolina

$36,658.72 USD total for 7 nights

Jun 26 – Jul 3, 2027

Luxury Sea Pines Home | 4th Row, Bikes included image 1

Luxury Sea Pines Home | 4th Row, Bikes included image 2

Luxury Sea Pines Home | 4th Row, Bikes included image 3

Luxury Sea Pines Home | 4th Row, Bikes included image 4

Luxury Sea Pines Home | 4th Row, Bikes included image 5

Luxury Sea Pines Home | 4th Row, Bikes included

5 bedrooms·5½ baths

Hilton Head Island • South Carolina

$3,380.00 USD total for 4 nights

Oct 27 – 31, 2026

Backyard Bliss: Poolside Fun & Fireside Nights

Backyard Bliss: Poolside Fun & Fireside Nights

The 19th Hole Loft – An Entertainment Escape with Games, Music & More!

The Heart of the Retreat: Spacious, Sunlit, and Designed for Connection

The Ultimate Bunk Suite: Sleep, Play & Unwind

1 Spanish Moss Road

5 bedrooms·5 baths

Hilton Head Island • South Carolina

$3,179.79 USD total for 4 nights

Oct 27 – 31, 2026

Welcome to our bright and open home.

Coastal Chic at Inland Harbour

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(95 reviews)

$2,770.22 USD $2,644.57 USD total for 7 nights

Apr 24 – May 1, 2027

The dining table easily seats 6 for meals.

Spacious first floor living and dining with sliding door to the deck

54" wall mounted TV, ceiling fan and layered lighting for evening wind down time.

Open floor plan for a great flow and great vacation. Island Song Villa will feel like your own personal villa.

View from the bottom of the stairs to the dining, kitchen, front door and 1st floor bedroom.

Island Song Villa

2 bedrooms·2 baths

Hilton Head Island • South Carolina

5(121 reviews)

$2,231.40 USD total for 7 nights

Nov 7 – 14, 2026

Oceanfront Estate Along Hilton Head’s Iconic Shoreline

Oceanfront Estate Along Hilton Head’s Iconic Shoreline

Oceanfront Estate Along Hilton Head’s Iconic Shoreline

14 Laughing Gull

Alfresco Dining Terrace with Pool & Ocean Views

14 Laughing Gull

7 bedrooms·8 baths

Hilton Head Island • South Carolina

$6,857.76 USD total for 4 nights

Oct 27 – 31, 2026

Upstairs Primary Suite

Patio with Grill and Golf Course Views

2227 Heritage Villa

3 bedrooms·3 baths

Hilton Head Island • South Carolina

$4,014.70 USD total for 3 nights

Mar 8 – 11, 2027

Bright Living and Dining Area with Room for Everyone

Private patio with seating just steps from the pool

Community Pool Just Steps from Patio!

Private patio with seating just steps from the pool

The MyStay Extras!

2203 Heritage Villa

4 bedrooms·4 baths

Hilton Head Island • South Carolina

$1,108.83 USD total for 3 nights

Nov 1 – 4, 2026

821 Ketch Court

821 Ketch Court

Enjoy Access to Harbour Town Pool Plus the Sun Deck Cafe!

View of Harbour Town Marina Across the Street

Across the Street from Lighthouse and Access to Marina Pathways

821 Ketch Court

3 bedrooms·3 baths

Hilton Head Island • South Carolina

$1,097.79 USD total for 3 nights

Nov 1 – 4, 2026