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YOUR HOME AWAY FROM HOME ON HILTON HEAD ISLAND

Nestled in the heart of South Carolina's Lowcountry, Island Head Rentals provides the perfect blend of luxury, adventure, and relaxation. Much like the iconic hospitality found at legendary retreats, Island Head Rentals delivers a tailored experience where every moment feels personal and unforgettable. With stunning waterfront properties, impeccable amenities, and unparalleled service, we create an inviting haven that combines casual elegance with the charm of coastal living. Whether you're here to soak up the sun, explore the waters, or simply unwind, Island Head Rentals invites you to discover your dream escape and make lasting memories in one of the most beautiful destinations in the world.

Red house graphic with a crescent moon and palm tree, enclosed in a circular marker design.
Sunset over a calm beach with colorful sky reflecting on wet sand and water.
Outdoor pool with surrounding patio chairs and palm trees, beige balustrade, sunny day.
Couple walking on a beach at sunset with the sun setting over the ocean.
Outdoor resort area with swimming pool, trees, pond, and buildings on a sunny day.
Sunset over a calm ocean with silhouette of trees on the horizon, vibrant orange and blue sky.
Indoor corridor with lush green plants and palm trees
Bicycle parked on a sandy beach with ocean and blue sky in the background, surrounded by a wooden fence and grass.
Evening view of a harbor with a lighthouse featuring red and white stripes, surrounded by boats and buildings, reflected in the water, under a clear blue sky.
Modern house exterior at night with illuminated patio, string lights, pool, lounge chairs, and surrounding trees.
A group of women sitting on a boat during sunset with the ocean in the background.
Beachfront house with gray roof and blue siding, surrounded by tall trees, overlooking a sandy beach and ocean.
Aerial view of a white boat on water with several people lounging on deck.
Aerial view of coastal resort area with marina, condominiums, and pool, surrounded by trees and near a body of water with a lighthouse visible in the background.
Aerial view of a coastal golf course with sand bunkers, lush green fairways, and surrounding residential homes. A boardwalk is visible, along with nearby trees and water bodies under a clear blue sky.
Child running on a beach with a flock of seagulls flying overhead.
Aerial view of a sandy beach with blue ocean waves, scattered beachgoers, and umbrellas along the shoreline.
Aerial view of a coastal golf course with water hazards, green fairways, and sand bunkers. Surrounding residential area with houses and trees, and nearby coastline with water bodies and a marina.
Group of people kayaking on a calm body of water, wearing life jackets.
Beach scene with three lounge chairs and blue umbrellas on sandy shore, overlooking the ocean at sunset. A person walks along the waterline.
Aerial view of a residential property with a swimming pool, patio furniture, and surrounding palm trees and greenery.
Aerial view of Hilton Head Island beach with ocean and buildings.
A blue boat with "Island Head" on the side is in the ocean. It is towing a parasail, with a person or people in the air under a blue parachute. The sky is bright with scattered clouds.
Aerial view of a coastal beach with sandy shores and ocean waves, bordered by a forested area and buildings in the background.
Aerial view of a coastal landscape during sunset with pink and orange clouds reflecting in the water, a small town, and expansive greenery.
Aerial view of a coastal area with a sandy beach, adjacent greenery, a swimming pool, and buildings surrounded by trees.
Sunset over a marsh landscape with tall grass, trees, and distant houses.
A blue and white boat marked 'Freeport Marina' embedded on grassy land surrounded by trees and greenery.
A sandy path surrounded by dense greenery, including palm trees and shrubs, leading through a lush wooded area under a clear blue sky. A partial view of a building is visible on the left side.
Aerial view of a golf course by a river and dense forest with houses, featuring green fairways, sand traps, and a marina in the distance.
Blue two-story house with white trim, front porch, and well-maintained landscaping set against a backdrop of green trees.

Discover the Best of the Lowcountry with Island Head Rentals

Immerse yourself in the charm of Hilton Head Island and experience everything the Lowcountry has to offer with Island Head Rentals. From stunning waterfront properties to unbeatable rates, we make it easy to create unforgettable memories. Whether you're seeking relaxation or adventure, our properties are your gateway to the perfect island escape.

  • 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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  • Beachfront house with gray roof, blue siding, white trim and porch, surrounded by tall trees with ocean view in the background.

    The Grand Daufuskie

    The ultimate island getaway in our oceanfront house on Daufuskie Island!

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  • Backyard view of a modern house with a swimming pool, illuminated string lights, lounge chairs, and greenery at dusk.

    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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  • Outdoor swimming pool with lounge chairs, apartment building in background, surrounded by trees.

    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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  • Scenic view of a resort with a swimming pool, surrounded by lush greenery and trees. There are buildings with balconies on the sides, and a small wooden bridge over a pond with fountains.

    Beachfront Bliss

    Stunning 2-bed, 2-bath, pet friendly oceanfront Palmetto Dunes condo

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  • Aerial view of a coastal resort with multiple buildings, green landscaping, and a pathway leading to a sandy beach and 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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  • Modern house with a two-car garage, surrounded by trees and a lawn.

    Sal and Babs Sea Pines Sanctuary

    Nestled along the picturesque coastline of Sea Pines on Hilton Head Island

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  • Aerial view of a coastal area with buildings surrounded by trees, a swimming pool, tennis court, and a beach in the background. A marker with a logo is positioned over 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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  • A modern blue two-story house with a white trim, front porch, manicured lawn, and surrounding 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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  • Luxurious multi-story beachfront villa with palm trees, outdoor pool, and terraces 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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  • Aerial view of a coastal town with beachfront properties, a sandy beach, and ocean in the background under a blue sky with scattered clouds.

    Seaside Sanctuary

    Charming coastal condo, just steps from the beautiful Hilton Head beaches!

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  • Beachfront balcony with a wooden table and high chairs, decorative wall art, and a red cooler

    Sandy Escape

    Located on the first floor of the closest building to the beach, you’re just steps away from the sand.

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  • Outdoor wooden deck with a circular glass table and four chairs, surrounded by trees and overlooking a scenic view of a forest at sunset.

    Marsh Oasis

    Welcome to your serene marsh-view retreat in the heart of Sea Pines!

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Book your stay today!

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

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Hassle Free Check-in

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Affordable Rates

Prime Locations

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Illustration of a palm tree, lounge chair, and cloud, symbolizing a tropical beach.

Families & Large Groups Welcome

Pet Friendly

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Simple stick figure depiction of a family with two adults and one child.
Four images of water activities: top-left shows people kayaking, top-right depicts a group of women on a boat at sunset, bottom-left features a boat with a parasailer in the air, and bottom-right displays an aerial view of people sunbathing on a boat.
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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!

Logo design featuring a stylized map icon and a partial crescent moon, with the text "The Island Head Connection." The design incorporates blue and black colors.
Logo of The Bike Doctor, Hilton Head Island, SC, featuring stylized bicycle gear and bold text.
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OUR AFFILIATES

Illustration of a bird in flight, with the text 'The Catalyst: RACISM x CATALYST.'

 @Islandheadrentals