Memorial Day
Looking for a spontaneous getaway this Memorial Day? We have fantastic last-minute bookings available on Hilton Head Island! Enjoy sun-soaked beaches, world-class golf courses, and vibrant dining options. If you're looking for a cozy beach cottage or a luxurious villa, we have the perfect properties for you. Don't miss out on making unforgettable memories—book your last-minute Memorial Day escape with us today!
We have no hidden fees! Our pricing is transparent, what you see is what you are paying. Click here to see our pricing breakdown.
18 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This spacious home embodies beach cottage vibes with its open layout and tastefully decorated interior! Soaring ceilings and lots of windows provide the great room with plenty of natural sunlight. In the living room, you will find plenty of plush seating arou
31 Sand Dollar Road
House -
$283.00 - $599.00 / per night
4
bedrooms
2
baths
10
guests
4.9
(20)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Brand New Construction 3rd row home in Palmetto Dunes!
130 Mooring Buoy is a beautiful 5-bedroom, 4.5-bath luxury home nestled in the beautiful Palmetto Dunes Oceanfront Resort. Just three rows from the beach, this home is meticulously designed for your perf
130 Mooring Buoy

House -
$746.00 - $1,846.00 / per night
5
bedrooms
4
baths
1
half bath
14
guests
5
(17)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
1206 Sea Crest is a spacious 2nd-floor corner villa in the Sea Crest complex where you can enjoy direct oceanfront views.
As you enter the front door into a small foyer, you will notice the very nice plank-style flooring. To the left is a guest bedroom with
1206 Seacrest
Villa -
$262.00 - $649.00 / per night
3
bedrooms
3
baths
10
guests
4.9
(18)
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
57 Fazio Villas

Villa -
$154.00 - $458.00 / per night
3
bedrooms
3
baths
7
guests
4.9
(25)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
No details were missed in this amazing 3-bedroom Palmetto Dunes home. Amazing golf course views greet you as soon as you walk in the door. The large living room\'s main sitting area has a sleeper sofa, a loveseat, and a desk.
Heading further through this ho
10 Troon

House -
$199.00 - $525.00 / per night
3
bedrooms
2
baths
1
half bath
8
guests
5
(18)
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
253 Captains Quarters
Villa -
$135.00 - $341.00 / per night
1
bedroom
1
bath
4
guests
4.9
(20)
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

House -
$614.00 - $2,035.00 / per night
6
bedrooms
6
baths
16
guests
5
(4)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Experience the perfect beach getaway at this newly renovated, top-floor villa in the heart of South Forest Beach. Just one block from the shore, dining, bars, Coligny Plaza, and Lowcountry Celebration Park, this chic 3-bedroom, 2-bath retreat comfortably slee
428 Forest Beach Villas
Villa -
$169.00 - $420.00 / per night
3
bedrooms
2
baths
7
guests
5
(7)
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
504 Barrington Arms
Villa -
$298.00 - $717.00 / per night
3
bedrooms
3
baths
8
guests
5
(21)
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
1 Sandy Beach Trail

House -
$550.00 - $1,381.00 / per night
6
bedrooms
5
baths
1
half bath
15
guests
5
(5)
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
3 Iron Clad
House -
$776.00 - $1,799.00 / per night
6
bedrooms
7
baths
12
guests
4.8
(23)
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 - $461.00 / per night
2
bedrooms
2
baths
6
guests
5
(10)
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