Workspace

Come work or play on Hilton Head Island!

We recognize the growing trend of remote work and the desire to balance productivity with relaxation. The properties below are all equipped with dedicated workspaces that allow you to seamlessly blend work with the pleasures of a tropical getaway on Hilton Head Island—truly allowing you to work in paradise.

Each of these specially curated properties offers high-speed internet and comfortable workstations. Whether it's a desk with a scenic view or a quiet office room, you can maintain productivity while indulging in the serene environment of a premier vacation destination. This unique setup not only enhances your work efficiency but also provides the flexibility to take breaks on the beach, play a round of golf, or enjoy a leisurely walk along the shore, all just moments away from your workspace.

Experience the best of both worlds by staying with us. Transform your work routine into a rejuvenating experience where each day ends with a sunset on the beach. Why settle for the usual when you can work, play, and relax in paradise? Book your perfect work-friendly getaway today!


Properties Available 44 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This amazing island getaway is nestled among the pines beside a lagoon on 1.9 acres in the heart of Sea Pines. This beach home offers beautiful high-end finishes in the huge eat-in kitchen and throughout, including the spacious dining room, living room, and
5 Calibogue Cay
House - Pet Friendly
$301.00 - $905.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half bath
Guests 10 guests
Rating 5 (3)
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. There are lots of books to read; there is lots of seating on
Hot HOT 93
30 Ruddy Turnstone | Ruddy Retreat
House - Pet Friendly
$436.00 - $1,828.00 / per night
Bedrooms 5 bedrooms
Bathrooms 6 baths
Guests 14 guests
Rating 4.9 (11)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Step into the coastal charm and be met with the open planned living area and dining area with a nice open window into the fully equipped kitchen. From this floor you will be able to step into the cozy sunroom which is the perfect spot to sit back and enjoy th
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150 Otter Road Fairway Collection Icon
House - Pet Friendly
$114.00 - $1,771.00 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 10 guests
Rating 4.9 (12)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. There is no need to look any further than oceanfront Beachside Bliss for your next family reunion or friends’ getaway, as this one-of-a-kind, 8,000-square-foot luxury home will spoil everyone lucky enough to come along! As soon as the sun comes up, your days
Hot HOT 141
43 South Beach Lagoon Icone Collection Icon
House -
$1,992.00 - $5,724.00 / per night
Bedrooms 8 bedrooms
Bathrooms 10 baths
Half Bathrooms 2 half baths
Guests 24 guests
Rating 4.6 (6)
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 Icone Collection Icon
House -
$660.00 - $2,276.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half bath
Guests 14 guests
Rating 5 (9)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Elegance is understated in this Lowcountry home, truly one of a kind. The setting could not get more perfect. This fabulous home offers 4 bedrooms, 2 master suites, 2 queen bedrooms, and a bunk room. The home boasts multiple living areas on the inside, a gour
51 Haul Away Fairway Collection Icon
House -
$442.00 - $1,387.00 / per night
Bedrooms 4 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 5 (10)
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
5 Jessamine Place
House -
$370.00 - $1,067.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 13 guests
Rating 5 (16)
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.
Oceanfront Oceanfront
Oceanfront
5305 Hampton Place Icone Collection Icon
Villa -
$215.00 - $738.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (22)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Single-level home with 3 bedrooms and a short walk to the beach! Enjoy close access to the beach in this fully renovated coastal chic ranch home with a hot tub and private outdoor shower! All-new kitchens, baths, furniture, and more ensure a comfortable and r
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6 East Garrison
House -
$226.00 - $642.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (17)
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
Oceanfront Oceanfront
Oceanfront
1013 Seacrest Icone Collection Icon
Villa -
$651.00 - $1,750.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 14 guests
Rating 5 (7)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This beautiful 2-bedroom, 2-bath villa has amazing views of the ocean. The large balcony has a table, chairs, and sun loungers to soak up the view. The balcony can be accessed through the living room sliding doors and one of the bedrooms. The first bedroom h
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Recently Updated
5303 Hampton Place
Villa -
$185.00 - $644.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 (10)
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
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3 Dune Lane Icone Collection Icon
House -
$649.00 - $2,840.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 16 guests
Rating 5 (21)

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