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.
137 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Thoughtfully refreshed and beautifully appointed, this 4-bedroom, 4.5-bath home in the heart of Sea Pines Plantation offers inviting coastal comfort with multiple gathering spaces, serene golf-course views, and a renovated pool deck perfect for relaxing days
2 Tupelo Drive
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
2390 Lighthouse Tennis Villa invites you to experience the Sea Pines Community on Hilton Head Island. In addition to its premier location surrounded by beautiful scenery, this well-appointed villa is an exceptional getaway retreat. From Harbour Town Marina to
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This 2 bedroom, 2-bath Beachside Tennis villa has panoramic views of Calibogue Sound. Located in the South Beach area of Sea Pines on the first floor of a five-story building, just steps to the pool and beach,
When entering the villa, you will find the mast
Welcome to 2538 Gleneagle Green, a beautifully updated, pet friendly Harbour Town villa managed locally by Island Time Hilton Head.
Located along the Harbour Town Golf Links, this spacious villa offers peaceful golf course views and a convenient Sea Pines location. Guests are just a short 5 minute walk from the shops and dining at Sea Pines Center
2538 Gleneagle Green
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.
This beautiful home is only steps away from the beach! Simply a lovely second-row home that invites you to come inside and enjoy. After a walk on the beach only steps from the home, relax by the pool, enjoy lunch and a nap on the deck, or sit by the fire pit
11 Grey Widgeon
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This oceanfront home sits in the prestigious Palmetto Dunes Resort and offers panoramic ocean views from every angle.
COMING WINTER 2026: A BRAND-NEW KITCHEN
10 Ketch is getting an exciting upgrade! This winter, the kitchen will undergo a complete transforma
10 Ketch
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Walk into this welcoming coastal retreat and immediately feel right at home. Thoughtfully designed with spacious gathering areas and comfortable accommodations, this property offers the perfect setting for a relaxing Hilton Head getaway.
As you enter the hom
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This 2-bedroom villa has been recently renovated and is the perfect oasis for a beach vacation. Nestled in the private oceanfront complex of Palmetto Dunes with perfect access to the beach and pool, the property features a complex pool, indoors and out! You w
1204 Villamare
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 two-story Fazio villa boasts peaceful golf course views and is perfect for a family vacation. With close proximity to the spectacular beaches of Palmetto Dunes with new furnishings, flooring and remodeled baths, and an oversized covered deck overlooking
26 Fazio Villas
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
From the moment you walk through the front door, natural light comes flooding in from the windows. The living room is the perfect place to relax with its comfortable furnishings, large screen TV, and access to the balcony through a glass sliding door located
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