FALL | 10% Off Select Properties
Unlock 10% off with a Non-Refundable Rate - USE CODE: FALL
Discover the beauty of fall with an exclusive 10% discount on select properties! Whether you're looking for a cozy 1 or 2-bedroom retreat or a spacious 3-bedroom villa, this is the perfect opportunity to enjoy these handpicked properties at a reduced rate.
Valid for new stays only, between 3-27 nights. Valid for stays between 8/16/24 - 11/21/24. All payments are final and non-refundable.
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
43 properties available
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!
533 Shorewood Place

Villa -
$216.00 - $664.00 / per night
2
bedrooms
2
baths
7
guests
4.8
(9)
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 -
$253.00 - $626.00 / per night
2
bedrooms
2
baths
6
guests
5
(17)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This cozy villa has two spacious bedrooms and large closets and is minutes from Harbour Town. When you first walk in, the kitchen is open to the dining area and living room. The living room offers plenty of seating to relax after a day out in the sun. Heading
2334 Racquet Club
Villa -
$135.00 - $529.00 / per night
2
bedrooms
2
baths
1
half bath
5
guests
5
(11)
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
510 Mainsail
Villa -
$178.00 - $470.00 / per night
2
bedrooms
2
baths
1
half bath
6
guests
5
(8)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
103 Seacrest is beautifully decorated and fully renovated for your comfort and convenience. Here, you will experience only the best. This charming property features two bedrooms, creating a cozy and inviting atmosphere for your stay. Allow me to paint a pictu
103 Seacrest

Villa -
$162.00 - $426.00 / per night
2
bedrooms
2
baths
6
guests
5
(6)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Enjoy the amazing ocean views from this lovely 2-bedroom, 2-bathroom renovated Windsor II villa. The dining table offers seating for 6, and the adjacent breakfast bar offers bar stool seating for 3.
Enjoy the spacious living room with a brand new sleeper sof
2216 Windsor II
Villa -
$204.00 - $525.00 / per night
2
bedrooms
2
baths
6
guests
5
(7)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This stunningly decorated 2-bedroom villa is just steps away from Harbourtown. The open-concept living space offers breathtaking views of the Calibogue Sound. Walking in on the first level, you are met with a spacious living room with comfy couches. Open to t
729 Schooner Court
Villa -
$158.00 - $906.00 / per night
2
bedrooms
2
baths
1
half bath
4
guests
4.8
(14)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
401 Windsor Place is a beautifully appointed villa in Palmetto Dunes with ocean views! Start your vacation memories today!
As you walk through the front door to be greeted with the ocean view, the light shines across the open-plan layout. An attractive livin
401 Windsor Place
Villa -
$190.00 - $537.00 / per night
2
bedrooms
2
baths
6
guests
4.9
(18)
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 -
$154.00 - $399.00 / per night
2
bedrooms
2
baths
6
guests
5
(6)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This magnificently remodeled North Shore Place villa features two bedrooms. Walking into an open-concept floor plan.
The master bedroom has a beautiful king bed and private ensuite bath. The ensuite bathroom features a walk-in shower. The guest bedroom has
103 North Shore Place
Villa -
$162.00 - $363.00 / per night
2
bedrooms
2
baths
6
guests
4.9
(11)
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 -
$115.00 - $295.00 / per night
1
bedroom
1
bath
1
half bath
4
guests
5
(6)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
1765 Bluff Villas is a stunning 3rd-floor villa in the South Beach area of Sea Pines. This completely renovated 2022 villa features comfortable furnishings in the living and dining areas. Come in to relax and take in the views. The private balcony is furnishe
1765 Bluff Villas
Villa -
$115.00 - $312.00 / per night
1
bedroom
1
bath
4
guests
5
(10)
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