Labor Day Vacation Rentals

Labor Day Weekend is the perfect way to say goodbye to summer, and Hilton Head Island offers everything you need for an unforgettable holiday escape. With warm temperatures, uncrowded beaches compared to the peak summer season, championship golf, waterfront dining, and endless outdoor adventures, Labor Day is one of the best times to experience the island. 

Whether you're planning a family vacation, a couples' retreat, or a long weekend with friends, Hilton Head Island combines coastal relaxation with exciting activities that make every day of your holiday memorable. It's an ideal opportunity to enjoy the island before the slower pace of fall arrives.

Early September brings warm ocean temperatures and sunny days that are perfect for spending time on Hilton Head's famous beaches. Stretch out on the sand with a good book, swim in the Atlantic, or take a leisurely walk along more than 12 miles of picturesque shoreline. 

Popular beach destinations like Coligny Beach Park, Sea Pines Beach Club, Folly Field Beach Park, and Driessen Beach Park offer convenient amenities and easy access, making it simple to spend the entire day by the ocean. The slightly smaller crowds compared to midsummer allow for a more relaxed beach experience while still enjoying the vibrant holiday atmosphere.


Properties Available 34 properties available
114 Forest Beach Villa offers spacious 2 bedroom, 2 bathroom condo with island views. This elevated 1st-floor is uniquely furnished with a King & Queen beds, making it the perfect getaway spot for 2 couples! The open floor plan gives that special "Lowcountry" feel! The living area offers open feeling. The private balcony can be accessed from slidi
Near Coligny Plaza Near Coligny Plaza
Near Coligny Plaza
Professionally Managed By Hilton Head Rentals - Town of Hilton Head Island Vacation Rental Permit #025797
Forest Beach Villa 114
Forest Beach
Total Price: $1,656.57
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.8 (5)
This fully updated 2 Bedroom, 2 Bath Ocean Villa is situated on the 3rd floor of the Atlantis Building within the Oceanfront Island Club Gated Community. Guests of 3301 Island Club can look forward to breathtaking oceanfront views and inspiring sunrises from their private balcony. The ocean view living room features comfortable updated furnishings
3rd Floor Oceanview 3rd Floor Oceanview
3rd Floor Oceanview
Professionally Managed By Hilton Head Rentals - Town of Hilton Head Island Vacation Rental Permit #021528
Island Club 3301
Folly Field
Total Price: $2,100.86
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.7 (13)
1 KINGSTON COVE Located in Shipyard Plantation this charming elevated 3 Bedroom home is just steps from the Pool and offers a spacious Sun Room overlooking a Large Tranquil Lagoon. The home features a new Kitchen with Granite Countertops and Center Island. 3 Flat Screen TV\'s and a Gas Grill. Guests of 1 Kingston Cove can Walk or Bike easily to th
Complex Pool Complex Pool
Complex Pool
Professionally Managed By Sea Turtle Getaways - Town of Hilton Head Island Vacation Rental Permit #028855
Kingston Cove 1
Shipyard
Total Price: $2,256.60
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (17)
This two-story townhouse has been beautifully updated and is located within the gated community of Shipyard Resort, perfect for both beach and golf enthusiasts. With 3 bedrooms and 3.5 baths, this townhouse is ideal for families and groups of friends. The first floor features a spacious living room with a sleeper sofa and flat screen TV. A half ba
Complex Pool Complex Pool
Complex Pool
Professionally Managed By Hilton Head Rentals - Town of Hilton Head Island Vacation Rental Permit #029457
Beachwalk 153
Shipyard
Total Price: $2,513.42
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (26)
196 COLONNADE CLUB Situated on the second floor, this lovely 3 bedroom villa offers tranquil views of the Lagoon & Golf Course. Each of the 3 bedrooms offers a Private Bath and there is a Private Screened in Balcony located off of the Living Room. The Kitchen has been completely updated and offers new Cabinetry, Granite Counter tops & Stainless St
Complex Pool Complex Pool
Complex Pool
Professionally Managed By Sea Turtle Getaways - Town of Hilton Head Island Vacation Rental Permit #026046
Colonnade Club 196
Shipyard
Total Price: $1,866.77
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 4.7 (13)
Welcome to 55 Wood Duck Road! Located within the Sea Pines Resort and in the Club Course neighborhood; this modernized single level ranch home offers 3 Bedrooms 3 Full Baths offering tranquil views of nature and the golf course. This Ground Level Home has a modern feel with a renovated Galley kitchen with updated stainless appliances and living
Pet Friendly Pet Friendly
Pet Friendly
Professionally Managed By Hilton Head Rentals - Town of Hilton Head Island Vacation Rental Permit #036457
Wood Duck Road 55
Sea Pines Pet Friendly
Total Price: $2,672.09
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 4.8 (7)
A Honeymoon Paradise or a perfect villa for a couple with a small family. Located in the heart of Harbour Town on Deer Island, the Sea Loft villas offer a unique vacation experience with nature. This particular villa is located at the end of the cul-de-sac and offers sound views to the left and marsh views to the right. Enjoy watching all of the
Harbour Town Harbour Town
Harbour Town
Professionally Managed By Sea Turtle Getaways - Town of Hilton Head Island Vacation Rental Permit #068870
Sea Loft 2065
Sea Pines Resort
Total Price: $1,840.52
Bedrooms 1 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.7 (4)
This Beautiful 2 Bedroom, 2 Bath Ocean Villa is situated on the 4th Floor of the Atlantis Building, within the Oceanfront Island Club Gated Community. It has been completely updated and offers breathtaking Oceanfront Views and inspiring Sunrises. The Ocean View Living Room features comfortable updated furnishings, a Large 55" Flat Screen TV, and a
4th Floor Oceanview 4th Floor Oceanview
4th Floor Oceanview
Professionally Managed By Hilton Head Rentals - Town of Hilton Head Island Vacation Rental Permit #071198
Island Club 3401
Folly Field
Total Price: $2,189.74
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (25)
This 2 Bedroom, 2 Bath Ocean Villa is situated on the 2nd floor of the Neptune Building within the Oceanfront Island Club Gated Community. Guests of 4205 Island Club can look forward to ocean views and inspiring sunrises from their private balcony. The ocean view living room features comfortable updated furnishings, TV, and ample seating on the p
2nd Floor Oceanview 2nd Floor Oceanview
2nd Floor Oceanview
Professionally Managed By Hilton Head Rentals - Town of Hilton Head Island Vacation Rental Permit #075198
Island Club 4205
Folly Field
Total Price: $1,834.29
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.6 (3)
This 2 Bedroom, 2 Bath Ocean Villa is situated on the 2nd floor of the Atlantis Building within the Oceanfront Island Club Gated Community. Guests of 3206 Island Club can look forward to ocean views and inspiring sunrises from their private balcony. The ocean view living room features comfortable updated furnishings, TV, and ample seating on the
Oceanfront Complex Oceanfront Complex
Oceanfront Complex
Professionally Managed By Hilton Head Rentals - Town of Hilton Head Island Vacation Rental Permit #028452
Island Club 3206
Folly Field
Total Price: $1,923.13
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (3)
15 BITTERN STREET This comfortable Beach Home with Cottage is casually decorated & offers the perfect setting for a relaxed beach vacation. Just 4 houses from the beach, the home features a private pool & poolside deck area. Guests of 15 Bittern can walk easily to Coligny Plaza with more than 60 shops and restaurants and the beach is literally jus
4th Row Near Ocean 4th Row Near Ocean
4th Row Near Ocean
Professionally Managed By Sea Turtle Getaways - Town of Hilton Head Island Rental Permit #028425
Bittern 15
Forest Beach
Total Price: $3,394.27
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.4 (32)
1106 Island Club is a slightly elevated 1st floor flat. The living room provides ample seating and an additional 55" flat screen TV. Sliding glass doors lead from the living room to the private balcony, which offers stunning views of the ocean. The dining room can comfortably seat 6 guests, with 3 additional breakfast bar stools for extra seating.
Oceanfront Complex Oceanfront Complex
Oceanfront Complex
Professionally Managed By Hilton Head Rentals - Town of Hilton Head Island Vacation Rental Permit #028621
Island Club 1106
Folly Field
Total Price: $1,745.44
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 4.8 (20)

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