View Our Properties
Our curated Collection of Hilton Head vacation rentals includes carefully selected homes and villas that are among the finest properties on the island. We offer luxury rentals in Hilton Head Island's most popular locations including Sea Pines, Palmetto Dunes, North Forest Beach, South Forest Beach, and Shelter Cove. Choose from an impressive selection of oceanfront rentals, private homes, and pet friendly rentals. We offer rentals with private pools as well as properties with access to heated pools in addition to many other sought-after amenities including keyless entry, wifi internet, updated furnishings, expansive porches, fireplaces, garage access, and more. Our vacation rentals are handpicked to help create a memorable experience during your Hilton Head vacation.
138 properties available
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.
This inviting lagoon front villa is ideally located in the heart of Palmetto Dunes, where peaceful water views and effortless beach access come together for a truly relaxing stay.
As you enter, you are welcomed into a bright and comfortable living space desi
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.
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.
Welcome to this inviting four-bedroom, three-bathroom home that combines bright open spaces with thoughtful design.
As you enter, you are welcomed into a light-filled interior. To the left of the entryway is the dining room, a warm and inviting space for mea
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 oceanfront home offers unforgettable views and a private pool, spa, a game room and an open great room. The open floor plan is a must and is perfect for entertaining. The gourmet kitchen features updated appliances and is perfect for gathering together.
7 Guscio Way
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Please Note: Exterior improvement work will be taking place at Lighthouse Road Villas beginning the week of 4/20/2026. Work will include tree removal, driveway resurfacing, new sidewalk installation, electrical updates, and landscaping. Tree removal will begi
3 Lighthouse Road Villa
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This waterfront villa in Sea Pines offers a blend of coastal charm and relaxed sophistication, with sweeping views of the Calibogue Sound from nearly every angle. Designed to host family and friends, the stunning villa features three bedrooms, two and a half
1922 South Beach Club
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Nestled within the exclusive Turtle Lane community, a private gated enclave located inside the gates of Sea Pines, 39 Turtle Lane offers a rare combination of privacy, luxury, and convenience just a three minute walk from the beach. Recently renovated from to
39 Turtle Lane
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
No details were missed in this amazing 3-bedroom Palmetto Dunes home. Amazing golf course views greet you as soon as you walk in the door. The large living room\'s main sitting area has a sleeper sofa, a loveseat, and a desk.
Heading further through this ho
10 Troon
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