Come to Hilton Head for Black Friday
Take a quick getaway and get ready for Black Friday. What better way to prepare for the holidays than to be near Tanger Outlets and the beach? Enjoy the frenzy of the deals and relax afterwards by the ocean. We have a 2-night minimum! Don't Miss Out.
This offer expires on November 28, 2023, and your dates of stay must be between November 24, 2023 - November 28, 2023.
We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown

39 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
253 Captain\'s Quarters, where amazing sunrises greet you in this contemporary one-bedroom villa. Coming this fall the kitchen will be renovated with new cabinets, counter tops and fixtures.
The villa is designed to offer a perfect blend of modern ameniti
Water View
Water View
Enjoy stunning water views from every room. Explore our water view properties.
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253 Captains Quarters
Villa -
1
bedroom
1
bath
4
guests
4.9
(27)
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.
Take in the ocean views at this wonderful 1-bedroom villa. The open kitchen and living area are well-appointed to accommodate all your needs. The kitchen has been recently renovated. The dining table seats 2. The living room has a queen sleeper sofa. The prim
Oceanfront
Oceanfront
Where the beach is your backyard. Discover our luxury oceanfront collection.
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212 Breakers
Villa -
1
bedroom
1
bath
4
guests
5
(36)
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
Oceanfront
Oceanfront
Where the beach is your backyard. Discover our luxury oceanfront collection.
Learn More
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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.
Notice: This property has recently undergone thoughtful updates, including a stunning new six-seat dining table, two stylish and cozy new chairs in the living room, and more updates to come. Updated photos coming January 2026.
This stunning villa has been th
Oceanfront
Oceanfront
Where the beach is your backyard. Discover our luxury oceanfront collection.
Learn More
Learn More
109 Shorewood Place
Villa -
2
bedrooms
2
baths
8
guests
5
(50)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
510 Mainsail is a gorgeous two-bedroom, two-and-a-half-bath, top-floor villa with breathtaking panoramic views of Shelter Cove Harbour. Designer-decorated, this property is perfect for a Hilton Head vacation and comfortably accommodates up to four people. Th
Water View
Water View
Enjoy stunning water views from every room. Explore our water view properties.
Learn More
Learn More
510 Mainsail
Villa -
2
bedrooms
2
baths
1
half bath
6
guests
5
(25)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This beautiful villa is perfect for relaxing and unwinding. The spacious great room features vaulted ceilings and unbelievable nature and water views.
Walk into this beautifully decorated villa and be greeted by lagoon views. The kitchen was recently update
3322 Lake Forest
Villa -
2
bedrooms
2
baths
5
guests
4.9
(38)
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
Where the beach is your backyard. Discover our luxury oceanfront collection.
Learn More
Learn More
2211 Seacrest
Villa -
2
bedrooms
2
baths
8
guests
4.9
(82)
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
1838 Beachside Tennis
Villa -
2
bedrooms
2
baths
6
guests
5
(54)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
533 Shorewood is an amazing 2-bedroom, 2-bathroom oceanfront villa with a pool and ocean views! This stunning beach condo sleeps 7 and is on the 5th floor with elevator access, featuring all new furniture and décor, a community pool, beach access, and more!
Oceanfront
Oceanfront
Where the beach is your backyard. Discover our luxury oceanfront collection.
Learn More
Learn More
533 Shorewood Place
Villa -
2
bedrooms
2
baths
7
guests
4.9
(33)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This gorgeous Sea Pines villa has been recently renovated and features golf and lagoon views. Walk into an open-concept kitchen, dining room, and living room. Relax on either of the comfortable couches in the living room and watch your favorite programs on th
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
3 Lighthouse Road Villa
Villa -
2
bedrooms
2
baths
6
guests
5
(98)
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
1584 Lagoon Villas
Villa -
2
bedrooms
2
baths
6
guests
5
(31)
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