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.
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.
504 Barrington Arms is a lovely three-bedroom, three-bathroom direct oceanfront condo on the fifth floor. Enjoy panoramic ocean views and updated furnishings and décor throughout. The dining area is adjacent to both the living room and the well-equipped kitch
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.
Can you just imagine hearing the birds chirping and the wildlife rustling in the greenery as you watch the herons wading in the lagoon? Can you hear the ping of the golfer\'s tee shot? Is the contact between the driver and the golf ball making the sweetest so
42 Stoney Creek
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Now Complete, Stunning Outdoor Upgrades!
The beautiful new saltwater heated plunge pool and spacious back deck are now finished and ready for its first guests to enjoy. Updated professional photos of the new outdoor space have now been uploaded so you can soo
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.
This stunning rental home offers a picturesque and convenient location, perfect for creating unforgettable vacation memories. This two-story retreat is designed for groups, with a private pool, a huge outdoor dining table, and five bedrooms with multiple bunk
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This fantastic 2nd row of the ocean is nestled in the palms of the Palmetto Dunes resort. With 6 bedrooms and 6.5 baths, this low-country home is the perfect getaway for family and friends!
A circular drive leads to a beautiful entrance way and wraparound p
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This completely renovated (2024) 2 bedroom, 2 bathroom property is perfectly located within steps of South Beach Marina, a short five minute walk to South Beach, and a three minute walk to tennis, pickleball, The Salty Dog Café, restaurants, and shopping.
T
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.
466 Captains Walk is a beautiful oceanfront villa is just steps away from the beach. This spacious 2nd floor villa has been completely renovated and offers full-length sliding glass doors opening to the private balcony in both the living room and master bedro
466 Captains Walk
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This breath-taking 4th-row home is one of a kind and has everything you need and more for your next Hilton Head vacation. The great room is spacious and is sure to keep guests feeling right at home with its stylish but cozy furnishings! Soaring ceilings and h
6 Grey Widgeon
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