SOUTH CAROLINA LUXURY VACATIONS – HILTON HEAD ISLAND
Finest Luxury Vacations offers you a variety of hand selected South Carolina Hilton Head Island vacation rentals. Choose wonderful vacation rentals throughout Hilton Head Island. South Carolina Vacation Rentals offers you the opportunity to explore this beautiful state from the beach to the scenic mountains.
BOOK YOUR SOUTH CAROLINA VACATION RENTALS DIRECT & SAVE!
Direct information is provided to you as a directory. Enjoy browsing through all our wonderful destinations for tropical villas, beach condos, secluded cabins. Don't forget about our exciting All Inclusive Packages, Wedding Destinations, Adult Only Getaways, Dude Ranches and so much more! You have the opportunity to see all we have to offer, so you can contact the provider directly for information, availability, reservations, special deals.
CHOOSE YOUR SOUTH CAROLINA VACATION DESTINATION:
EXCLUSIVE SHOWCASE COLLECTION:
FEATURING: VACATION TIME OF HILTON HEAD ISLAND SHOWCASE COLLECTION...
MAKE AMAZING VACATION MEMORIES IN HILTON HEAD ISLAND
With Vacation Time of Hilton Head Island, you'll have a Hilton Head vacation experience you'll savor for years. We have nearly 150 Hilton Head vacation rentals for you and your family to choose from. Our selection includes plenty of Hilton Head oceanfront rentals and Hilton Head rentals with ocean views, and we have condos and villas at many of the popular Hilton Head resorts including Seaside Villas, Seascape Villas, and Ocean Dunes Villas.
We look forward to welcoming you to HHI very soon……and for years to come. It’s Vacation Time.
HILTON HEAD ISLAND PROPERTIES...
Coconut Cabana
8 Guests | 3 Bedrooms | 3 Bathrooms | Private Heated Pool & Lush Gardens
Starting at $444 per Night
Step into paradise at Coconut Cabana, where lush tropical gardens, twinkling string lights, and a private heated pool set the stage for the perfect Sea Pines retreat. Nestled in a quiet, coastal enclave just 0.6 miles from the beach, this thoughtfully designed ranch home offers effortless comfort…
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Tidal Tranquility
14 Guests | 6 Bedrooms | 5 Bathrooms | Elegance of Low Country Living
Starting at $560 per Night
Welcome to Tidal Tranquility – Where breathtaking marsh views meet the elegance of lowcountry living. From serene sunsets to modern amenities, this is more than just a vacation—it’s a memory waiting to be made…
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“BEACHSIDE HILTON HEAD ISLAND”
Lookout Lagoon
6 Guests | 3 Bedrooms | 3 Bathrooms | Perfect Getaway in South Beach Marina
Starting at $384 per Night
Welcome to Lookout Lagoon, your perfect getaway in the beautiful South Beach Marina. Lookout Lagoon offers a blend of luxury, comfort, and adventure—whether you’re seeking a tranquil escape or an activity-filled vacation, this villa has everything you need…
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Cardinals Cradle
10 Guests | 4 Bedrooms | 3.5 Bathrooms | Modern Comfort with Pool & Spa
Starting at $499 per Night
Where modern comfort meets timeless Lowcountry charm, Cardinal's Cradle is an elegantly renovated 4-bedroom, 3.5-bathroom ranch-style home in Sea Pines, offering an inviting open layout, private heated pool & spa, and a serene screened-in porch…
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Heritage House
12 Guests | 4 Bedrooms | 4 Bathrooms | Private Golf Course Retreat
Starting at $735 per Night
Where modern elegance meets timeless coastal charm, Heritage House is a beautifully redecorated 4-bedroom, 4-bathroom home, offering golf course views, a private heated pool, and an expansive outdoor living space…
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Vicino al Mare
10 Guests | 4 Bedrooms | 4 Bathrooms | A Serene Coastal Escape
Starting at $500 per Night
Experience the perfect blend of comfort and coastal charm at Vicino al Mare, a beautifully designed 4-bedroom, 4-bathroom ranch-style home located in the heart of Sea Pines. Just 0.5 miles from the beach…
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Sea Breeze Bliss
8 Guests | 3 Bedrooms | 2 Bathrooms | Unwind in Style
Starting at $296 per Night
Indulge in the coastal charm and refined tranquility of Sea Breeze Bliss, your idyllic short-term rental nestled just 0.8 miles from the pristine beaches of Hilton Head Island. This cozy yet elegant ranch invites you to unwind in style…
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Marsh View
10 Guests | 3 Bedrooms | 3 Bathrooms | A Spacious Pet-Friendly Retreat
Starting at $399 per Night
Discover Marsh View, a charming home in Sea Pines, Hilton Head. Just 0.5 miles from Harbour Town and 1.7 miles to the Sea Pines Beach Club, this pet-friendly getaway offers panoramic marsh views, a private pool, and expansive outdoor living spaces…
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Sweet Carolina
10 Guests | 4 Bedrooms | 3 Bathrooms | Charming Pet-Friendly Retreat
Starting at $275 per Night
Experience the best of Sea Pines at Sweet Carolina, a 4-bedroom, 3-bathroom home offering modern comfort, spacious living, and access to premier community amenities. Nestled in the Carolina Place neighborhood, this home is perfect for families, groups, and pet owners…
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Serenity by the Sea
8 Guests | 3 Bedrooms | 3 Bathrooms | A True Haven for Guests & Pets
Starting at $321 per Night
Nestled in the tranquil enclave of Lawton Woods in Sea Pines, Hilton Head, “Serenity by the Sea” is a delightful short-term rental offering a peaceful escape. This 3-bedroom, 3-bath ranch provides ample space for 8 guests, ensuring a serene and comfortable stay…
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Southern Charm
12 Guests | 4 Bedrooms | 4.5 Bathrooms | A Coastal Beauty
Starting at $505 per Night
“Southern Charm” is an exquisite short-term rental nestled in the heart of Sea Pines, Hilton Head, offering a spacious and luxurious escape. The beautiful backyard is adorned with a private pool, creating a serene oasis for relaxation…
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Hideaway
6 Guests | 2 Bedrooms | 2 Bathrooms | Charming Coastal Retreat
Starting at $296 per Night
Escape to Hideaway, a charming 2-bedroom, 2-bathroom retreat in the Lawton Woods neighborhood of Sea Pines. With a private plunge pool, stylish interiors, and pet-friendly accommodations, Hideaway offers a perfect blend of comfort and relaxation…
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Pelican's Perch
9 Guests | 4 Bedrooms | 3.5 Bathrooms | Classic Beach Charm
Starting at $489 per Night
Discover Pelican’s Perch, a 4-bedroom, 3.5-bathroom 4th-row beach home in Sea Pines, Hilton Head. Just 800 feet from the beach, this upside-down coastal retreat offers a private heated pool, screened-in porch, and spacious living areas…
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Sunny Shores
10 Guests | 4 Bedrooms | 3 Bathrooms | Truly Unique Home
Starting at $375 per Night
“Sunny Shores” is a truly unique and modern 4-bedroom, 3-bathroom short-term rental nestled in the heart of Sea Pines, Hilton Head. This distinctive house boasts breathtaking views of the Heron Point golf course, thanks to the expansive glass along the back of the property…
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Cotton Cottage
8 Guests | 3 Bedrooms | 2 Bathrooms | Charming Coastal Retreat
Starting at $296 per Night
Tucked away on a peaceful cul-de-sac in Sea Pines, Cotton Cottage is a 3-bedroom, 2-bathroom coastal retreat designed for relaxation and comfort. This pet-friendly home features a fully fenced backyard, a private heated pool, and a beautifully styled interior…
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Barefoot Bungalow
6 Guests | 2 Bedrooms | 2 Bathrooms | Resort Style Backyard with Pool
Starting at $396 per Night
Where upscale comfort meets coastal charm. Tucked away in the sought-after Lawton Woods neighborhood of Sea Pines, Barefoot Bungalow is a beautifully designed 2-bedroom, 2-bathroom ranch-style home that sleeps up to 6 guests…
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Fairway Oasis
11 Guests | 5 Bedrooms | 4.5 Bathrooms | Resort Style Backyard with Pool
Starting at $499 per Night
A luxurious home nestled in the heart of Sea Pines on Hilton Head Island. Combining Southern charm with modern convenience, this stunning retreat offers breathtaking views of the 11th green of the Heron Point golf course. Private pool, spa, screened-in porch…
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Peek-of-Blue
17 Guests | 6 Bedrooms | 5 Bathrooms | Classic Beach House Steps to Ocean
Starting at $586 per Night
Escape to Peek of Blue, a 6-bedroom, 5-bathroom second-row beach home in Sea Pines, Hilton Head. Just 800 feet from the beach, this spacious and value-packed getaway is perfect for large families or groups seeking a classic beach retreat…
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Peek-of-Blue
17 Guests | 6 Bedrooms | 5 Bathrooms | Classic Beach House Steps to Ocean
Starting at $586 per Night
Escape to Peek of Blue, a 6-bedroom, 5-bathroom second-row beach home in Sea Pines, Hilton Head. Just 800 feet from the beach, this spacious and value-packed getaway is perfect for large families or groups seeking a classic beach retreat…
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Driftwood
8 Guests | 4 Bedrooms | 3 Bathrooms | Perfect Blend of Retro Style & Coastal Luxury
Starting at $352 per Night
Welcome to Driftwood—a coastal haven where cherished memories are made. Imagine vintage charm perfectly blended with modern comfort, just steps away from the beach, nestled in the stunning Sea Pines community. Driftwood is a pet-friendly, second-row single-family beach home…
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Tropical Retreat
12 Guests | 4 Bedrooms | 4 Bathrooms | Your Coastal Escape in Sea Pines
Starting at $655 per Night
Tropical Retreat is a designer-decorated haven that redefines coastal luxury. This home follows the classic upside-down house design, placing the main living and kitchen areas upstairs for an elevated perspective. With a private pool and spa, a screened-in porch…
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Coastal Chic
12 Guests | 4 Bedrooms | 4.5 Bathrooms | A Designer-Owned Retreat
Starting at $499 per Night
Where elegance meets comfort, Coastal Chic is a beautifully designed 4-bedroom, 4.5-bathroom home in the heart of Sea Pines, offering stylish interiors, ample gathering spaces, and a private heated pool. Blending sophistication with a relaxed coastal vibe…
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Island Time
10 Guests | 4 Bedrooms | 3 Bathrooms | A Tranquil Golf View Retreat
Starting at $546 per Night
Discover Island Time, a beautifully designed coastal escape in Sea Pines, Hilton Head. Just 0.5 miles from the beach this spacious ranch-style home offers the perfect blend of comfort, relaxation, and stunning golf course views…
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Beachwalk Cottage
10 Guests | 4 Bedrooms | 4 Bathrooms | Coastal Retreat Steps to Beach
Starting at $446 per Night
Beachwalk Cottage is a beautifully updated 4-bedroom, 4-bathroom home in the heart of Sea Pines, just 400 feet from the beach—a quick 2-minute walk to the shoreline. With a private heated pool, spacious screened-in porch, and an open, airy layout…
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Kahuna Cove
8 Guests | 3 Bedrooms | 3.5 Bathrooms | A Luxury Outdoor Oasis
Starting at $499 per Night
Escape to Kahuna Cove, a stunning retreat in Sea Pines, Hilton Head. Just 0.7 miles from the beach, this pet-friendly home offers an incredible resort-style backyard with a massive private pool, spa, fire pit, and an outdoor cabana…
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Dream Catcher
12 Guests | 5 Bedrooms | 4 Bathrooms | Perfect Hilton Head Escape
Starting at $569 per Night
Where classic coastal charm meets modern comfort, Dream Catcher is a beach house nestled 2nd row from the beach in the prestigious Sea Pines community. With an “upside-down” layout, a private heated pool & spa, and an expansive outdoor living space…
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Beach & Bunkers
14 Guests | 5 Bedrooms | 5.5 Bathrooms | Luxury Golf Course Retreat
Starting at $769 per Night
A luxurious retreat nestled 3rd row from the beach on Hilton Head Island. Offering breathtaking views of the 18th fairway of the Atlantic Dunes golf course, this home seamlessly combines beachside proximity with golf-course grandeur…
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