Stay Awhile This Fall
Settle into Island Time for a little longer and enjoy more of what makes Hilton Head so special. With fewer crowds, beautiful weather, and a slower coastal rhythm, fall is the perfect time to extend your stay and truly unwind.
Enjoy 10% off stays of 8 to 27 nights for stays between 9/14/26- 11/19/26.
Promo code: EIGHTPLUS
We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.
This offer cannot be combined with other offers. Valid for new stays only.
136 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This completely remodeled Sea Pines home sits on the 11th fairway and 15th green of the Harbour Town Golf Course!
With 5 bedrooms and 6 bathrooms, this sunlight-filled home can host up to 14 guests comfortably. As you enter the home, you are met with an extr
100 Baynard Cove
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Indulge in the epitome of coastal living at this meticulously maintained 1-bedroom, 1.5-bath renovated villa in the prestigious Barrington Villas. Every aspect of this retreat has been thoughtfully curated to offer a blend of elegance and comfort, promising a
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This fantastic 2nd row of the ocean is nestled in the palms of the Palmetto Dunes resort. With 6 bedrooms and 6.5 baths, this low-country home is the perfect getaway for family and friends!
A circular drive leads to a beautiful entrance way and wraparound p
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This renovated 3-bedroom, 3-bath townhome features quartz countertops, soft-close cabinets, glass tile backsplash, LVP flooring, smooth ceilings, stunning tile showers, all new lighting, and new stainless steel appliances in the fully stocked gourmet kitchen.
283 Turnberry Villas
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Your perfect retreat for relaxation and adventure! Whether you\'re here to unwind with family, explore the surrounding area, or simply enjoy time together, this spacious and beautifully designed home is the ideal place to create unforgettable memories. Get re
32 Full Sweep
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Brand New Construction 3rd row home in Palmetto Dunes!
130 Mooring Buoy is a beautiful 5-bedroom, 4.5-bath luxury home nestled in the beautiful Palmetto Dunes Oceanfront Resort. Just three rows from the beach, this home is meticulously designed for your perf
130 Mooring Buoy
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Indulge in the tranquil charm of a beach vacation at 25 Singleton Beach, a grand and luxurious 7-bedroom retreat designed for unforgettable seaside getaways. This stunning brand-new home boasts large glass doors and windows that flood the interior with natura
25 Singleton Beach
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Modern comforts meet the classic styling of this traditional beach home. If you are looking for a house that has the look and feel of the beach house from your childhood memories, look no further. The home has gone through a complete renovation to restore it
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
1206 Sea Crest is a spacious 2nd-floor corner villa in the Sea Crest complex where you can enjoy direct oceanfront views.
As you enter the front door into a small foyer, you will notice the very nice plank-style flooring. To the left is a guest bedroom with
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
435 Captain\'s Walk overlooks the pool out to the ocean! Lots of recent updates!
435 Captain\'s Walk is a second-floor, 3-bedroom, 3-bathroom end unit that overlooks the pool and out to the ocean. A beautiful, updated villa with great views—you couldn\'t ask
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
As soon as you step through the front door of Feline Beachy, expansive views of the Atlantic Ocean greet you, framed by natural dunes and swaying palms. The living area is warm and inviting, furnished with Tommy Bahama Bali Hai rattan bamboo pieces that bring
4202 Windsor Court North
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Notice: This property has recently undergone thoughtful updates, including a stunning new six-seat dining table, two stylish and cozy new chairs in the living room, and more! Brand new photos have been uploaded as of March 2026.
This stunning villa has been
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