May on the water
Before the rush of summer, Hilton Head slows to something truly special. Mornings begin with a sunrise cast, afternoons drift by on the water, and evenings end with the sun melting into the horizon.
Slip into Island Time this May and enjoy 15% off on all our properties for any stay between 05/01/2026 - 05/29/2026.
Promo Code: MAYATTHEBEACH
This offer cannot be combined with other offers. Valid for new stays only.
138 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Perfectly situated within the heart of Palmetto Dunes and just a short stroll from the beach, 3 Cartgate offers the ideal combination of spacious living, thoughtful updates, and relaxed coastal comfort. Recently enhanced with new flooring throughout much of t
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Step inside to an impressive, oversized entryway that immediately sets the tone for this exceptional home. The grand entrance features a sweeping spiral staircase to the left, convenient elevator access, and direct entry to the garage, all thoughtfully design
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!
Find tranquility in this cozy two-bedroom, two-and-a-half-bath Palmetto Dunes villa
8103 Wendover Dunes
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This home is spacious and relaxing 3-bedroom home in the charming, gated community of Sea Pines. Open the door to experience a serene view of a private lagoon shaded by palm trees and live oaks dripping with Spanish moss. An abundance of natural sunlight stre
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This charming Sea Pines home is 4th row from the beach and features 5 bedrooms along with 5 bathrooms and 2 half bathrooms to host 14 guests very comfortably.
The first floor features a very open floor plan that offers easy access between the multiple living
2 Royal Tern
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.
Welcome to this stunningly renovated fourth row beach home in the heart of Palmetto Dunes, where luxurious indoor living, resort-style outdoor spaces, and breathtaking lagoon views come together on an oversized double lot just moments from the beach. Guests w
135 Mooring Buoy
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This expansive property features five bedrooms and two separate entrances, providing ample space and privacy for larger groups. This property boasts multiple living areas, ensuring plenty of room for everyone to spread out and relax.
This amazing villa featu
1013 Seacrest
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This renovated 3-bedroom, 3-bath townhome features quartz countertops, soft-close cabinets, glass tile backsplash, LVP flooring, smooth ceilings, stunning tile showers, all new lighting, and new stainless steel appliances in the fully stocked gourmet kitchen.
283 Turnberry Villas
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
2517 Windsor Place is a beautifully appointed three-bedroom, three-bathroom oceanfront villa that blends spacious design with effortless coastal elegance. Ideal for golf getaways, family vacations, or couples traveling together, this villa offers a thoughtful
2517 Windsor II
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 equipped with a new gas grill. The living room has a small desk space, perfect for any last-minute
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Enjoy the amazing ocean views from this lovely 2-bedroom, 2-bathroom renovated Windsor II villa. The dining table offers seating for 6, and the adjacent breakfast bar offers bar stool seating for 3.
Enjoy the spacious living room with a brand new sleeper sof
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