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136 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This completely remodeled Sea Pines home sits on the 11th fairway and 15th green of the Harbour Town Golf Course!
With 5 bedrooms and 6 bathrooms, this sunlight-filled home can host up to 14 guests comfortably. As you enter the home, you are met with an extr
100 Baynard Cove
House -
5
bedrooms
5
baths
1
half bath
14
guests
5
(14)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
A brand-new game room has been added to Bedroom 3! This space now features a Pac-Man arcade console along with a wide selection of board games, making it the perfect setup for family game nights and friendly competition.
This 3-bedroom, 3-bathroom villa is a
591 Queens Grant | Palmetto Dunes
Villa -
3
bedrooms
2
baths
1
half bath
8
guests
4.9
(35)
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
Pet-Friendly
Pet-Friendly
Your entire family deserves time away... even the family dog. Preview our selection of pet friendly properties.
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28 Corine Lane
House -
5
bedrooms
4
baths
15
guests
4.9
(38)
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
517 Barrington Court
Villa -
1
bedroom
1
bath
1
half bath
4
guests
5
(29)
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
House -
5
bedrooms
5
baths
1
half bath
16
guests
4.9
(35)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This property will be undergoing construction and unavailable for rental during 2026. If you have any questions, please reach out to us at or call
This beautifully upgraded vacation home combines sophisticated design, high-end finishes, and abundant natur
6 Genoa Court
House -
4
bedrooms
4
baths
10
guests
5
(2)
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
Pet-Friendly
Pet-Friendly
Your entire family deserves time away... even the family dog. Preview our selection of pet friendly properties.
Learn More
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2390 Lighthouse Tennis
Villa -
1
bedroom
1
bath
4
guests
4.9
(39)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Enjoy endless coastline views from this corner villa on the fifth-floor face of the Windsor Court South building in Palmetto Dunes. Take in breathtaking panoramic views from the screened porch or one of the many balconies that can be found off the living room
3507 Windsor Court South
Villa -
3
bedrooms
3
baths
6
guests
5
(27)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
2 bedroom, 3 bathroom Moorings villa close to the beach (650 feet from beach access; less than a two-minute walk) and the pool (located right outside the villa) in the sought-after Palmetto Dunes Oceanfront Resort on Hilton Head Island This Palmetto Dunes vil
23 The Moorings
Villa -
2
bedrooms
3
baths
6
guests
5
(46)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Beautiful 3-bedroom villa with 3 full baths So close to the truly spectacular beaches of Palmetto Dunes Remodeled kitchen and baths Oversized covered deck overlooking the community pool.
Overlooking the Fazio Golf Course in Palmetto Dunes, this spacious, new
Pet-Friendly
Pet-Friendly
Your entire family deserves time away... even the family dog. Preview our selection of pet friendly properties.
Learn More
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57 Fazio Villas
Villa -
3
bedrooms
3
baths
7
guests
4.9
(30)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
245 Captains Quarters is the ideal villa for a small family getaway, offering picturesque views of the Intracoastal Waterway from your own private balcony, allowing you to fully immerse yourself in the tranquil atmosphere of Hilton Head.
The fully stocked k
Water View
Water View
Enjoy stunning water views from every room. Explore our water view properties.
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245 Captains Quarters
Villa -
2
bedrooms
2
baths
6
guests
5
(2)
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
Pet-Friendly
Pet-Friendly
Your entire family deserves time away... even the family dog. Preview our selection of pet friendly properties.
Learn More
Learn More
7484 Anchorage Villa
Villa -
2
bedrooms
2
baths
6
guests
5
(25)
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