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!


Properties Available 25 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This oceanfront stunner was built in 2019 and offers amazing views as well as direct access to the beach with a private boardwalk. Walk into an amazing great room to unwind from a day out in the sun. The living room has two couches and two comfy chairs that
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103 Dune Lane Icone Collection Icon
House - Pet Friendly
$1,391.00 - $4,999.00 / per night
Bedrooms 7 bedrooms
Bathrooms 7 baths
Half Bathrooms 1 half bath
Guests 20 guests
Rating 5 (12)
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
Pet-Friendly Pet-Friendly
Pet-Friendly
26 Bradley Circle
House - Pet Friendly
$389.00 - $1,351.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 16 guests
Rating 5 (7)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This oceanfront stunner is located in South Forest Beach to offer panoramic ocean views and places you only minutes away from fun at Coligny Plaza. Upon entry, you walk into the first-floor great room of the home, which consists of a living room, kitchenette
Oceanfront Oceanfront
Oceanfront
12 Cassina Lane Icone Collection Icon
House -
$705.00 - $2,651.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 12 guests
Rating 4.8 (13)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Can you just imagine hearing the birds chirping and the wildlife rustling in the greenery as you watch the herons wading in the lagoon? Can you hear the ping of the golfer\'s tee shot? Is the contact between the driver and the golf ball making the sweetest so
42 Stoney Creek Fairway Collection Icon
House -
$558.00 - $2,959.00 / per night
Bedrooms 7 bedrooms
Bathrooms 7 baths
Half Bathrooms 1 half bath
Guests 15 guests
Rating 4.8 (9)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This beautiful home is only steps away from the beach! Simply a lovely second-row home that invites you to come inside and enjoy. After a walk on the beach only steps from the home, relax by the pool, enjoy lunch and a nap on the deck, or sit by the fire pit
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11 Grey Widgeon Icone Collection Icon
House -
$543.00 - $1,912.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 12 guests
Rating 4.7 (14)
**THIS OCEANFRONT HOME IS A NON-SMOKING PROPERTY (INCLUDING OUTDOOR SPACES) AND DOES NOT ALLOW ANY PETS OR ANIMALS IN OR ON PROPERTY.** Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This stunning oceanfront oasis sits in the heart of Palmetto Dunes. As soon as you step through the front doors, the luxu
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19 Armada Icone Collection Icon
House -
$2,168.00 - $4,199.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half Bathrooms 2 half baths
Guests 15 guests
Rating 5 (9)
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
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6 Grey Widgeon Icone Collection Icon
House -
$563.00 - $1,509.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 16 guests
Rating 4.9 (13)
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
Hot HOT 64
3 Dune Lane Icone Collection Icon
House -
$781.00 - $2,542.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 16 guests
Rating 5 (20)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. The grand entrance staircase will transport you to another world through the Italian-style portico, where you are immediately greeted by an expansive ocean view. Walking into the main house, you are greeted by a beautiful, curved staircase leading you up to
Oceanfront Oceanfront
Oceanfront
7 Junket Icone Collection Icon
House - Pet Friendly
$1,124.00 - $3,623.00 / per night
Bedrooms 6 bedrooms
Bathrooms 7 baths
Half Bathrooms 2 half baths
Guests 14 guests
Rating 4.8 (8)
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
4 Quail Street
House -
$432.00 - $1,011.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.9 (10)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This stunning Palmetto Dunes beach home has recently undergone a full renovation, boasting 5 bedrooms and offering a short stroll to both the beach and the Robert Trent Jones Golf Course. The highlight of this retreat is the brand new private pool, perfect fo
New Pictures New Pictures
New Pictures
13 Sea Lane Fairway Collection Icon
House -
$406.00 - $1,599.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 16 guests
Rating 5 (12)
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
3 Iron Clad
House -
$701.00 - $1,844.00 / per night
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 12 guests
Rating 4.7 (12)

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