Spring Break
Spring Break is calling. Escape to Hilton Head Island and enjoy sun-soaked days, beautiful beaches, and effortless coastal living.
From now through May 15th, 2026, our homes and villas are available with a 3-night minimum stay, making it easy to plan the perfect getaway on your schedule.
Please note: Sea Pines properties require a 4-night minimum stay during Heritage Week (April 11–19, 2026).
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.
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.
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 charming Palmetto Dunes home offers expansive golf course views and features multiple living spaces to host large groups with ease.
On the main level, the living room offers comfortable seating around the flatscreen TV and fireplace, as well as direct v
176 Mooring Buoy
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.
Your perfect retreat for relaxation and adventure! Whether you\'re here to unwind with family, explore the surrounding area, or simply enjoy time together, this spacious and beautifully designed home is the ideal place to create unforgettable memories. Get re
32 Full Sweep
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This beautifully furnished and decorated home overlooks the Palmetto Dunes 11-mile lagoon and is just a 10-minute walk to the beach. With 4 bedrooms and 4.5 bathrooms, a gourmet kitchen, a private pool, and the beautiful Robert Trent Jones golf course, this i
39 Port Tack
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Discover your serene escape in the oceanfront complex of South Forest Beach! With direct beach access and a large on-site pool (heated in March & April and October & November), this villa combines relaxation and convenience, just steps from the ocean and a s
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.
Welcome to a beautifully designed retreat where warm natural light, effortless flow, and thoughtful comforts create an unforgettable stay. From the moment you walk in, the home opens into a bright and spacious layout that invites relaxation.
To the left of t
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.
Take in the ocean views at this wonderful 1-bedroom villa. The open kitchen and living area are well-appointed to accommodate all your needs. The kitchen has been recently renovated. The dining table seats 2. The living room has a queen sleeper sofa. The prim
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Indulge in the epitome of coastal living at this meticulously maintained 1-bedroom, 1.5-bath renovated villa in the prestigious Barrington Villas. Every aspect of this retreat has been thoughtfully curated to offer a blend of elegance and comfort, promising a
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