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104 rentals found
12 Whelk, Steps to the Beach, Private Po...
4.3
(12)

Welcome to 12 Whelk Street, Hilton Head Island's premier vacation destination, where beachside luxury meets unmatched convenience. Just 145 feet from the pristine sands of Bradley Beach, this newly modernized four-story property offers striking...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Sandcastle by the Sea - brand-new, priva...
4.6
(16)

Sandcastle 97Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in a gated beachside community, Sandcastle by the Sea is a family-friendly 6BR/4BA...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
Beachfront beauty with pool access - fir...

Sea PointeOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This chic five-bedroom home is just steps away from Singleton Beach and the shared community pool...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
Lovely house with gourmet kitchen, scree...
4.0
(6)

Black SkimmerOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This property in the Sea Pines development sits among the natural beauty of Hilton Head Island's...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
Sea Pines Home w/ Private Pool, Family-F...
4.6
(17)

North Sea Pines Drive 44Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please read our important pool heat information to help you have the best vacation...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Oceanfront, Sea Pines, Pool & Private Be...
5.0
(65)

This oceanfront beach home is for a marvelous family (or multi-family) holiday. It combines an original but refreshed beach "bungalow" with an extension that adds a master bedroom suite, office/study, formal dining room, powder room, elevator, and...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
Two-story home with pool, balcony, deck,...
5.0
(5)

Piping Plover 12Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Piping Plover 12 is an immaculate and gorgeous 2nd row home located near South Beach in...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 20
Spacious family home with WiFi, private ...
4.4
(21)

Summer HouseOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'With a fireplace, a pool, cavernous common areas, and plenty of beds to lay your head down at...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
9 Singleton Beach, Newly Renovated, Ocea...
5.0
(2)

*New Construction Update(Spring 2025): Updated Kitchen, Updated Master Bathrooms, Updated Half Bathroom, (Jack n Jill Bathrooms to be refreshed winter 2025), New Washer and Dryer sets*9 Singleton Beach, Hilton Head Island. This oceanfront gem is a...

  • Hilton Head
  • 7 Bedrooms
  • 5 Bathrooms
  • Sleeps 20
3rd row Luxury rental - Low Min nights  ...
5.0
(14)

* Enormous Open floor plan for generational gatherings* Luxury Furnishings & Linens* Hot Tub / Pool on living level * Luxury Soaps, Shampoo's & Lotions * Free Packages for some stays* Welcome Packages upon arrival * 24 hour access to...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Close to beach, pickleball, tennis & gol...
4.0
(2)

Flagg 2-Serene RetreatOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'You’ve found gold with this charming, family-friendly home, with a serene yet...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Secluded Sea Pines retreat with private ...
4.2
(13)

Royal RetreatOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to this luxury estate boasting two separate poolside structures and ample seating areas...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 20
Beautiful Oceanfront Home with Large Pri...

This enormous six bedroom seven bathroom oceanfront home has everything you've ever wanted in a vacation! As you enter the home you're greeted by a cavernous ceiling with huge modern chandelier. On your left is the formal dining room, which...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Oceanfront home with huge windows and a ...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This handsome, nine-bedroom Beachcomber home sports a private pool and spa and provides broad living spaces, as well as fantastic vistas of the beach and the...

  • Hilton Head
  • 9 Bedrooms
  • 10 Bathrooms
  • Sleeps 28
10 Collier Beach, Oceanfront, Elevator, ...
4.9
(7)

10 Collier Beach, Hilton Head Island is an escape to heaven in this striking 6-bedroom, 7-bathroom oceanfront home, offering impressive ocean vistas and the ultimate in privacy. Unwind by the private pool, appreciate direct access to the beach, and...

  • Hilton Head
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 16
32 Corine, Pickleball, Seasonal Beach Sh...
4.8
(24)

32 Corrine Lane is a charmingly decorated 6-bedroom, 6-bath open concept home that is really a extravagant getaway for families or enormous groups. The presence of three primary king bedroom suites, private balconies and a private pool ensure that...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 15
5 Bedroom Home w/ Private Pool & 6Seater...
5.0
(5)

Welcome to Island Impact Vacation Rental at 91 Sandcastle Court, Hilton Head, South Carolina! Constructed in 2020, this new single family home was designed with the goal to make many memories and allow others to do the same while on vacation. This...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
Dog-friendly home with private pool, WiF...
4.5
(10)

Crabline Court 31Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find the ideal group hideaway at this family-friendly beach home, located just a half-mile...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14