Large Groups
Bring Everyone To Hilton Head Island
Planning your next family vacation, family reunion, work retreat, or special event? Hilton Head Island is the perfect destination, and Island Time offers the ideal accommodation solutions for large groups. Choose from our expansive selection of spacious homes designed to cater to big families and groups, ensuring everyone stays comfortably together under one roof.
Our large vacation homes on Hilton Head Island not only provide ample space and privacy but also boast a range of luxurious amenities like private pools, gourmet kitchens, and outdoor entertainment areas, perfect for any group gathering. Staying in one of our homes allows your group to enjoy shared experiences and create lasting memories without the confines of separate hotel rooms.
Choosing a vacation home on Hilton Head Island for your large group means convenience, comfort, and connection. Enjoy the ease of group bookings, and the advantage of cost-effective per-person pricing. Let our expert team help you find the perfect home for your group's needs, making your stay as seamless as possible.
Embrace the beauty and community of Hilton Head Island for your next big event. Our properties offer the perfect backdrop for creating new stories and celebrating together. Book your group's stay with us and experience the best that Hilton Head has to offer!
24 properties available
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.
9 Armada is a gorgeous second row home directly on the beach path in Palmetto Dunes Resort. This spacious 6,800 square foot home is perfect for entertaining, dining, reading, or relaxing!
The kitchen features granite counters, two sinks, two dishwashers, a w
9 Armada
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.
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.
Brand new photos have been uploaded as of January 2026! Take a look at the amazing updates this property has recently made.
This oceanfront stunner was built in 2019 and offers amazing views as well as direct access to the beach with a private boardwalk.
W
103 Dune Lane
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Fabulous two-story second row home The balconies and decks overlook the incredible pool. Take the secret path through the canopy and reach the beach in a 1-minute walk. This 6-bedroom, 5.5-bath home with 2 living rooms sleeps 15 and promises unforgettable fam
1 Man O War
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Views, views, and more views! What better way to start your day than listening to the surf, enjoying the beautiful scenery of the marsh with active wildlife, and the ocean just beyond while sipping your coffee on the deck? An expansive, gorgeous beach is just
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This beautifully updated 5-bedroom, 4-bath home with a 2-car garage, elevator, and private pool is located at Singleton By The Beach. This home is located by the beautiful Chaplin Park, which offers free tennis, pickleball, basketball courts, and walking trai
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.
With beautiful craftsmanship throughout the well-appointed house. The ground level has a newly refinished pine floor and an open-plan design, with the large kitchen overlooking the cozy living room equipped with a comfortable sleeper sofa. There are lots of b
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
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