Sleeps up to 16
Ideal for large families, reunions & groups.
Discover the perfect getaway with our spacious vacation rentals on Hilton Head Island, accommodating up to 16 guests. Ideal for large families, reunions, or group vacations, these properties offer ample space, luxurious amenities, and stunning locations. Enjoy fully-equipped kitchens, multiple living areas, numerous bedrooms, and private pools. Pair these amenities with our signature Luxury Concierge services, and you can rest assured that your vacation will be relaxing and memorable.
Situated close to the island's beautiful beaches, golf courses, tennis & pickleball courts and outdoor activities, our rentals ensure a memorable stay for everyone. Book your Hilton Head Island vacation rental today and experience unparalleled comfort and convenience for your entire group in this picturesque coastal paradise!
26 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Nestled along the scenic fairways of the renowned Atlantic Dunes Golf Course, this brand new 6-bedroom, 6-bath home in Sea Pines captures the essence of upscale coastal living. 169 North Sea Pines welcomes you with a blend of contemporary design and Southern
169 North Sea Pines Drive
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This expansive property features five bedrooms and two separate entrances, providing ample space and privacy for larger groups. This property boasts multiple living areas, ensuring plenty of room for everyone to spread out and relax.
This amazing villa featu
1013 Seacrest
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
5 Jessamine Place is only a 10-minute walk to the best beach on Hilton Head Island!
This ranch-style cottage home is newly renovated and beautifully furnished. It offers four bedrooms and four bathrooms to comfortably host up to 13 guests. Nestled on a quie
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.
This stunning 5-bedroom, 5.5-bathroom oceanfront home is nestled in the heart of North Forest Beach, offering an unforgettable coastal experience with sweeping views of the Atlantic. As you step through the bright and welcoming entryway, you are immediately
3 Dune Lane
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This oceanfront home sits in the prestigious Palmetto Dunes Resort and offers panoramic ocean views from every angle.
The great room, kitchen, and dining area make up the great room of the home; the extremely open floor plan allows for an easy flow and plent
10 Ketch
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.
This breath-taking 4th-row home is one of a kind and has everything you need and more for your next Hilton Head vacation. The great room is spacious and is sure to keep guests feeling right at home with its stylish but cozy furnishings! Soaring ceilings and h
6 Grey Widgeon
Welcome to The Sandbox! Newly renovated and outlined with elegance in every detail, this 3-story oceanfront home is truly perfect for your next Hilton Head Island family getaway.
This home has an extremely open floor plan that allows an easy flow between the living room, kitchen, and dining area. The living room is well-appointed and spacious, an
9 Guscio Way
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Located in the heart of Palmetto Dunes, 49 Sea Lane is a newly constructed custom home thoughtfully designed for gathering, relaxation, and making lasting vacation memories. Featuring seven bedrooms, five full bathrooms, one half bathroom, multiple living spa
49 Sea Lane
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.
This charming Sea Pines home is 4th row from the beach and features 5 bedrooms along with 5 bathrooms and 2 half bathrooms to host 14 guests very comfortably.
The first floor features a very open floor plan that offers easy access between the multiple living
2 Royal Tern
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