Stay Awhile This Fall
Settle into Island Time for a little longer and enjoy more of what makes Hilton Head so special. With fewer crowds, beautiful weather, and a slower coastal rhythm, fall is the perfect time to extend your stay and truly unwind.
Enjoy 10% off stays of 8 to 27 nights for stays between 9/14/26- 11/19/26.
Promo code: EIGHTPLUS
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.
This offer cannot be combined with other offers. Valid for new stays only.
136 properties available
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.
This beautifully updated 5-bedroom, 4-bath home with a 2-car garage, elevator, and private pool is located at Singleton By The Beach. This home is located by the beautiful Chaplin Park, which offers free tennis, pickleball, basketball courts, and walking trai
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Tucked away on a quiet street in the heart of Sea Pines, 10 Battery Road is a charming coastal retreat designed for both relaxation and connection. With its bright open design and multiple areas to gather, this single-story home invites guests to unwind and e
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
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This property has recently undergone thoughtful updates, including a full kitchen renovation with new appliances, a fresh paint job, brand new bedding, brand new flooring, updated primary bathroom and more! Brand new photos have been uploaded as of March 2026
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
2519 Windsor Place is a beautifully appointed three-bedroom, three-bathroom oceanfront villa offering elevated coastal living from its top-floor location. With sweeping views of the Atlantic and the calming rhythm of the waves just beyond, this villa creates
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 3rd-floor villa is recently updated and places you just minutes outside of the world-famous Harbour Town. With 2 bedrooms and 2 bathrooms, this Sea Pines villa can sleep up to 4 people comfortably. The living room is illuminated with natural light and ha
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Nestled along the scenic fairways of the renowned Atlantic Dunes Golf Course, this brand new 6-bedroom, 6-bath home in Sea Pines captures the essence of upscale coastal living. 169 North Sea Pines welcomes you with a blend of contemporary design and Southern
169 North Sea Pines Drive
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 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.
Note: New photos of the backyards brand new fire pit and hot tub coming soon!
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
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