LARGE HOMES
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![Aerial view of a blue beach house with a gray roof surrounded by tall trees, located near a sandy shoreline and ocean.]()
The Grand Daufuskie
The ultimate island getaway in our oceanfront house on Daufuskie Island!
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![Outdoor area with a modern two-story house, a swimming pool, and string lights at night. The patio features lounge chairs and Adirondack chairs, surrounded by greenery and a palm tree.]()
The Island Head Original
5 houses from the ocean. Big Family or group, dog friendly, 6-br, 4-ba beach home.
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![Modern two-story house with a white exterior, two-car garage, surrounded by trees and a well-manicured lawn.]()
Sal and Babs Sea Pines Sanctuary
Nestled along the picturesque coastline of Sea Pines on Hilton Head Island
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![Two-story blue house with white trim, large windows, and a front porch with chairs, surrounded by a manicured garden and trees.]()
Deja Blue - Steps To Beach
Your perfect family vacation destination in South Forest Beach, 6-BR with pool and hot tub.
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![Large luxury house with pool and palm trees in a tropical setting.]()
Dune Side 7
Just 50 steps from Singleton Beach, a luxurious retreat with ocean views and a private pool
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![Outdoor deck with round table and chairs overlooking a forest at sunset]()
Marsh Oasis
Welcome to your serene marsh-view retreat in the heart of Sea Pines!
VILLAS & CONDOS
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![Heart Of Harbour Town]()
Heart Of Harbour Town
Our pool view 4-bedroom, 4-bathroom townhouse in the heart of Harbour Town
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![Outdoor swimming pool in front of an apartment building with lounge chairs and a small pool house.]()
Barefoot Bliss at The Spa
First floor & easy access! Luxury 2-br, 2-ba condo at the Spa in Hilton Head
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![Outdoor pool area with lounge chairs and trees, surrounded by buildings and a pond with a fountain.]()
Beachfront Bliss
Stunning 2-bed, 2-bath, pet friendly oceanfront Palmetto Dunes condo
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![Aerial view of beachfront resort with large buildings near the ocean.]()
Sea Side Escape
Discover the epitome of coastal living at Sea Side Villas II in HHI with this inviting apartment.
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![Aerial view of a coastal area with dense greenery, residential buildings, a swimming pool, and tennis courts. The ocean is visible in the background. A location marker with a red house icon and palm tree is placed on one building.]()
Fiddler's Lux Villa
Large Balcony, 2 BR/2 BA Fiddler's Cove villa. Located on the quiet third floor,
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![Aerial view of a beachfront area with a long stretch of sandy beach, ocean waves, and nearby residential buildings surrounded by trees.]()
Seaside Sanctuary
Charming coastal condo, just steps from the beautiful Hilton Head beaches!
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![Balcony with wooden table and chairs overlooking beach and dunes, decorative wall art, and cooler.]()
Sandy Escape
Located on the first floor of the closest building to the beach, you’re just steps away from the sand.
The Island Head Difference
Experience the charm and beauty of Hilton Head Island with Island Head Rentals. We offer a curated selection of vacation properties designed to meet your needs, whether you’re seeking a peaceful retreat or an adventure-filled getaway. From exceptional amenities to unbeatable locations, Island Head Rentals is your gateway to the Lowcountry lifestyle.
Fun Activities
Hassle Free Check-in
Affordable Rates
Prime Locations
Families & Large Groups Welcome
Pet Friendly
THE ISLAND HEAD CONNECTION
Island Head’s two owners have teamed up with a former employee, now a major player in Hilton Head’s real estate scene, and two real estate professionals to take the brand to the next level in short-term rentals.
As a guest enjoy direct bookings through Island Head Concierge for all experiences and fun things to do, including:
Bike Rentals
Watersports
Reservations
Private charters, and more.
Plus, bookings of 7+ nights include a free 2-hour private sunset cruise for up to 14 guests at select properties!
