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Get 10% off your June vacation! Use promo code: JUNE10.
Experience comfort and sophistication in our Hilton Head Island properties. Relax in spacious living areas, enjoy well-equipped kitchens, and unwind on private balconies or patios with breathtaking views.
Valid for new stays only. Not valid with any other offers. Offer expires 06/10/25, and you must book your vacation between 05/31/25 and 06/21/25
We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.
102 properties available
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
150 Otter Road
Experience coastal elegance at its finest in this beautifully remodeled 2-bedroom, 2-bathroom oceanfront villa, perfectly situated on the 3rd floor for sweeping views of the Atlantic Ocean. Wake up to the tranquil sound of waves and breathtaking ocean vistas from every room in this serene retreat.
The spacious primary bedroom features a plush king
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.
This villa has been fully remodelled in a light coastal design, creating an inviting and serene retreat. This charming space is the perfect spot for a peaceful island getaway, combining modern comfort with classic coastal elegance.
As you step inside, you\'l
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This villa has plenty of space to move around. Walk into the first floor, where you have the kitchen, dining room, and living room leading out to a small patio. The living room has a small desk space, perfect for any last-minute work that needs to get done. T
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
You\'re going to love this Captain\'s Walk villa for one of the best panoramic ocean views on Hilton Head Island, for being centrally located within mid-island on new paved pathways, for having a golf course on the property, and for having conveniently locate
450 Captains Walk
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Direct Oceanfront 3 bedrooms Villa with gorgeous renovations
This 3-bedroom, 3-bath villa offers a comfortable vacation for friends or family groups. Enjoy ocean views with access to your private balcony through the living room or master bedroom. The living
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
3 Bedroom Villa in Harbour Town Area, Newly Renovated, and Golf View. Gorgeous renovations in 2020 make this villa the right choice for you. As you enter, you are greeted with a two-story, open, and airy space. This open-concept living, dining, and kitchen ar
2371 Racquet Club
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This recently updated Palmetto Dunes villa places you only minutes away from the beautiful sandy beaches of Hilton Head. Come in and relax on the comfy sectional. The living room is warm and inviting, with a pullout sofa bed. This villa has an open living roo
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This charming two-bedroom, two-story townhouse is located in the highrise building called Oceanview at the oceanfront Island Club, featuring a lagoon view from the private deck. Walk right out to the grounds from the deck or spend your evening cooking dinner
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This home is a stunning haven nestled in the heart of Sea Pines, where luxury meets comfort in a beautiful retreat. Exciting updates are coming to the house, including the addition of a brand-new bunk room! Keep an eye on the website—updated photos will be av
18 Willow Oak
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This 2 Bedroom 2 Bathroom villa is located in Palmetto Dunes in the tranquil Queens Grant neighborhood. This open plan, pet friendly villa is the perfect place for a peaceful Island escape. With it\'s open plan, and coastal blues interior, you\'ll find every
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