View Our Properties
Our curated Collection of Hilton Head vacation rentals includes carefully selected homes and villas that are among the finest properties on the island. We offer luxury rentals in Hilton Head Island's most popular locations including Sea Pines, Palmetto Dunes, North Forest Beach, South Forest Beach, and Shelter Cove. Choose from an impressive selection of oceanfront rentals, private homes, and pet friendly rentals. We offer rentals with private pools as well as properties with access to heated pools in addition to many other sought-after amenities including keyless entry, wifi internet, updated furnishings, expansive porches, fireplaces, garage access, and more. Our vacation rentals are handpicked to help create a memorable experience during your Hilton Head vacation.
137 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This stunning coastal home welcomes you with a beautiful blue exterior and an expansive front porch featuring rocking chairs and a hanging bench, creating the perfect spot to relax and enjoy the island breeze.
Inside, the home feels grand and open with an ab
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
5305 Hampton Place is a two-primary suite villa with stunning ocean views! There is a great bedroom separation, full of natural light, granite, and stainless-steel appliances. This unit is located on the 3rd floor and can be accessed via stairs or elevator.
5305 Hampton Place
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Exciting updates have just been completed at this property! A brand-new 5th bedroom is now finished and fully furnished with a full-size bed and an ensuite jack-and-jill style bathroom. Updated photos have been completed as of January 2026.
Elegance is under
51 Haul Away | Haul Away Haven
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.
This oceanfront home offers unforgettable views and a private pool, spa, a game room and an open great room. The open floor plan is a must and is perfect for entertaining. The gourmet kitchen features updated appliances and is perfect for gathering together.
7 Guscio Way
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Penthouse 3-bed villa overlooking the world-famous Harbour Town Yacht Basin, just steps away from Harbourtown
A great room with dual sofas facing a large flat-screen TV A set of sliders gives entrance to a whimsically tiled patio with a postcard-perfect view
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This completely renovated Palmetto Dunes villa is sure to make you feel right at home! Welcome to 89 The Moorings, featuring 2 bedrooms and 3 bathrooms with enough room to host up to 8 guests very comfortably. Guests can enjoy the feel of brand new flooring,
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Enjoy endless coastline views from this corner villa on the fifth-floor face of the Windsor Court South building in Palmetto Dunes. Take in breathtaking panoramic views from the screened porch or one of the many balconies that can be found off the living room
3507 Windsor Court South
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This stunning 5-bedroom, 5.5-bathroom house is nestled in the heart of North Forest Beach. Ideally situated, it boasts direct access to the pristine sandy shores of the Atlantic Ocean, making it a beach lover\'s dream come true. Step inside, and you\'ll be gr
3 Dune Lane
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
6 Gunnery is a spacious and inviting home ideally located in the heart of Sea Pines. Nestled halfway between Harbour Town and South Beach Marina, this property offers the perfect combination of convenience and tranquility. Enjoy an easy 10-minute walk or 5-mi
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This waterfront villa in Sea Pines offers a blend of coastal charm and relaxed sophistication, with sweeping views of the Calibogue Sound from nearly every angle. Designed to host family and friends, the stunning villa features three bedrooms, two and a half
1922 South Beach Club
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Welcome to a beautifully designed retreat where warm natural light, effortless flow, and thoughtful comforts create an unforgettable stay. From the moment you walk in, the home opens into a bright and spacious layout that invites relaxation.
To the left of t
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