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Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. You\'re going to love this Captain\'s Walk villa for one of the best panoramic ocean views on Hilton Head Island, for being centrally located within mid-island on new paved pathways, for having a golf course on the property, and for having conveniently locate
Oceanfront Oceanfront
Oceanfront
450 Captains Walk Icone Collection Icon
Villa -
$245.00 - $1,184.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (33)
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
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New Property
245 Captains Quarters
Villa
$149.00 - $384.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Nestled in the charming Burke\'s Beach on Hilton Head Island, this remarkable 6-bedroom, 5 1/2-bathroom home is a coastal paradise that offers a luxurious and comfortable lifestyle. As you step inside, you\'ll be greeted by a spacious and well-designed interi
Hot HOT 59
1 Sandy Beach Trail Icone Collection Icon
House -
$550.00 - $1,841.00 / per night
Bedrooms 6 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 15 guests
Rating 5 (3)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 2211 Seacrest has new LVT floors with walk-in showers, a garden tub, double vanities, and more! This is a wonderful 2-bedroom, 2-bathroom villa located on the second floor of Building 2. Walk-in to the open-concept living space, perfect to spread out and rel
Oceanfront Oceanfront
Oceanfront
2211 Seacrest
Villa -
$135.00 - $527.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.8 (20)
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
Water View Water View
Water View
1866 Beachside Tennis Villa
Villa -
$165.00 - $718.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (16)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 1401 Villamare is going under a complete renovation and will be rental ready in Summer 2025! This is a 4th floor villa with breathtaking oceanfront views. When entering this villa the main living area, kitchen, dining and master bedroom are to your right. The
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New Property
1401 Villamare
Villa
$182.00 - $1,047.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
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
35 Shell Ring
House -
$148.00 - $2,213.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 5 (5)
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 Fairway Collection Icon
House -
$511.00 - $1,460.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 14 guests
Rating 5 (7)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This Sea Pines villa is outfitted with elegance in every detail, offering guests complete coastal luxury. An alluring yet spacious layout offers guests plenty of room to spread out, all while being together. Upon entry, to the left, you will find the fully
Water View Water View
Water View
1838 Beachside Tennis Icone Collection Icon
Villa -
$180.00 - $921.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (17)
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. The living room has a small desk space, perfect for any last-minute work that needs to get done. T
16 Ocean Club
Villa -
$135.00 - $394.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (13)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Be Our Guest Beach Villa is proud to unveil a top-to-bottom remodel that makes it a showpiece of the Queens Grant Neighborhood. This end-unit villa offers an abundance of windows and sliding glass doors, allowing natural sunlight to flow in with views of the
672 Queens Grant
Villa - Pet Friendly
$205.00 - $552.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 11 guests
Rating 5 (5)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This beautifully upgraded vacation home combines sophisticated design, high-end finishes, and abundant natural light, creating a truly remarkable getaway. Located just a short walk from Harbour Town, its convenient location makes it unforgettable. The main
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New Property
6 Genoa Court
Villa
$208.00 - $3,570.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests

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