New on the Collection
Be one of the first to stay to stay in one of these hand selected vacation properties on Hilton Head Island!
Escape to paradise and experience the epitome of luxury in one of our newest additions to our vacation rental program on Hilton Head Island. Nestled along the pristine shores of the Atlantic Ocean, our newest properties promises an unforgettable retreat for discerning travelers seeking the perfect blend of comfort and sophistication.
Step inside and be greeted by expansive living spaces bathed in natural light, thoughtfully appointed with designer furnishings and modern conveniences. From gourmet kitchens equipped with top-of-the-line appliances to spacious bedrooms adorned with plush bedding and luxurious linens, every detail has been carefully selected to ensure a truly indulgent experience.
Hilton Head Island is truly an oasis away from everyday life. You can walkour 12 miles of premier beaches, golf on one of over 30 golf course, play tennis or pickleball at one of our racquet clubs or public courts, or just idle away the day by the private pool at your vacation home. However you choose to spend your holiday on Hilton Head, our accommodations are the perfect "home" base.
21 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
A charming first-floor villa with a walkout balcony offering breathtaking views of the golf course. Nestled in the heart of Sea Pines, this delightful retreat combines comfort and convenience, making it the perfect getaway for golfers and vacationers alike.
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Discover the ultimate lagoon-front escape at this beautifully renovated home, complete with a private fishing dock and just a 5- to 10-minute walk from the beach, the Dunes House, and the Tennis and Pickleball Center.
Step into the first level, where new vi
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
6 Gunnery is a spacious and inviting home ideally located in the heart of Sea Pines. Nestled halfway between Harbour Town and South Beach Marina, this property offers the perfect combination of convenience and tranquility. Enjoy an easy 10-minute walk or 5-mi
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
4 Ocean Club offers you the perfect beachfront getaway in South Forest Beach! With direct beach access and a private, heated pool, this villa offers the best of Hilton Head Island vacationing.
Step into the inviting first floor, where you\'ll find a fully-eq
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
245 Captains Quarters is the ideal villa for a small family getaway, offering picturesque views of the Intracoastal Waterway from your own private balcony, allowing you to fully immerse yourself in the tranquil atmosphere of Hilton Head.
The fully stocked k
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Indulge in the tranquil charm of a beach vacation at 25 Singleton Beach, a grand and luxurious 7-bedroom retreat designed for unforgettable seaside getaways. This stunning brand-new home boasts large glass doors and windows that flood the interior with natura
25 Singleton Beach
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This home has been beautifully remodeled in the heart of Sea Pines, where coastal charm meets modern comfort. Thoughtfully designed with relaxation in mind, this stunning property offers ample space, brand-new kitchen appliances, and inviting interiors perfec
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Discover the ultimate island retreat in this newly built three-story home, perfectly designed for a relaxing getaway. With its elegant interiors and thoughtfully curated outdoor spaces, this stunning property is an oasis of comfort and style.
The first floo
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Nestled in the heart of Sea Pines, this coastal retreat offers the perfect blend of comfort and convenience for your next vacation.
As you step into the villa, you’ll find a welcoming dining area to your right, perfect for family meals or casual gatherings.
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 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 2 Bedroom 2 Bathroom villa is located in Palmetto Dunes in the tranquil Queens Grant neighborhood. This open plan villa is the perfect place for a peaceful Island escape. With it\'s open plan, and coastal blues interior, you\'ll find everything you need
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