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!
39 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This stunning home has recently undergone a series of thoughtful updates designed to enhance both comfort and style. A brand new fifth bedroom has been added, now featuring a comfortable queen bed to provide additional sleeping accommodations. The property ha
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Located on a quiet street, with Harbour Town Golf Course just steps away, 35 Battery has a light, bright feel and an open, single-level floor plan. Upon entering the front door, a foyer leads guests directly into the living/dining room, which has cathedral ce
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This home has been freshly updated with brand new exterior paint, kitchen countertops, renovated bedrooms and bathrooms, a new grill, and more exciting upgrades throughout! Photos have been updated to reflect these updates as of February 2026.
This pet-frien
36 Red Oak
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
43 South Beach Lagoon
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
From the moment you arrive, the home welcomes you with its inviting façade featuring two balconies, a cozy front porch, and a secluded swing-bench nook tucked to the side, perfect for morning coffee or a quiet evening moment.
Stepping inside, you\'re greeted
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Beautifully updated 3-bedroom villa in Shelter Cove. Come in, take a seat, and relax in the living room. The living room, kitchen, and dining room have an open layout. The kitchen has granite countertops, new stainless steel appliances, and smooth ceilings.
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This property now offers an exciting new amenity with a free pickleball and tennis pass in Palmetto Dunes, which includes two free hours of court time every day of your stay!
Indulge in the tranquility of coastal living with this exquisite 3-bedroom, 3-bathr
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This inviting Sea Pines retreat is tucked just three rows from the beach and offers sweeping views of the 18th hole of the Atlantic Dunes Golf Course. Designed to host up to 12 guests, Beaches and Bunkers features five beautifully appointed bedrooms, each wit
8 Beach Lagoon | Beaches and Bunkers
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 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
5303 Hampton Place
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
13 Sea Lane
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This beautiful oceanfront property features three spacious bedrooms, providing ample space for a relaxing and enjoyable stay. A gorgeous foyer with a spiral staircase ascends to a massive open floor plan with open living, dining, and kitchen areas with high-e
101 Seacrest
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