Labor Day Vacation Rentals

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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 76 properties available
203 SHOREWOOD This lovely 2nd floor villa offers Panoramic Oceanfront views and has been tastefully decorated. The Oceanfront Master Bedroom offers a King bed, Flat Screen TV & DVD player plus a Private Bath. The second bedroom features 2 Twin beds, TV, DVD player and Private Bath. The Living Room provides breathtaking Oceanfront Views and there i
Hot HOT 54
Shorewood 203
Forest Beach
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.7 (58)
12 SURF SCOTER This charming 4th Row Ocean Home appeals to Sea Pines Beach Lovers of all ages. The Great Room features hardwood flooring and cozy, comfortable furnishings and the large Screened Porch offers relaxing evening breezes and overlooks your Private Pool & Spa. With King, King, 2 Bunks and Queen + Twin bed. This home is ideal for couple
Hot HOT 58
Surf Scoter 12
Sea Pines Resort
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 4.7 (31)
This 4th floor 2 bedroom, 2 bathroom condo is located directly on the oceanfront and offers stunning views of the Atlantic Ocean. Guests can watch the dolphins and shrimp boats go by, and even catch a glimpse of the Tybee Island Lighthouse on the horizon. The condo has an open floor plan that can accommodate up to 6 guests. The living area has a q
Hot HOT 54
Shorewood 408
Forest Beach
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (32)
308 SHOREWOOD Ideal for beach lovers, this charming 3rd floor villa offers exceptional Oceanfront views and is within easy walking distance to Coligny Plaza with more than 60 shops & restaurants. The Oceanfront Master bedroom offers a King bed & Private Bath and the Guest bedroom has 2 Twin beds & Private Bath. The villa offers an oceanfront Livin
Hot HOT 52
Shorewood 308
Forest Beach
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.5 (31)
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
Hot HOT 12
Kingston Cove 1
Shipyard
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (17)
310 SHOREWOOD Ideal for beach lovers, this charming 3rd floor villa offers exceptional Oceanfront views and is within easy walking distance to Coligny Plaza with more than 60 shops & restaurants. The Oceanfront Master Bedroom offers a King bed & Private Bath and the Guest bedroom has a Queen & Twin bed plus a Private Bath. The villa offers an Ocea
Hot HOT 18
Shorewood 310
Forest Beach
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.6 (54)
2256 HERITAGE This 2 bedroom townhouse is the perfect choice for guests who enjoy Golf, Tennis & all of the various amenities that Sea Pines has to offer. This updated villa offers a King in the master and a Queen and Twin in the 2nd bedroom. Overlooking a lagoon, with a peaceful setting where you can watch the different birds of the Island. Guest
Hot HOT 11
Heritage Villa 2256
Sea Pines Resort
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 4.8 (16)
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
Hot HOT 67
Island Club 3401
Folly Field
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (25)
240 EVIAN This charming townhouse is nestled within the Private Community of Evian in Shipyard Plantation. This nicely appointed two story townhouse offers tranquil Lagoon & Golf Views. The Living Room features a large Flat Screen TV & Wet Bar. Each bedroom also has a Flat Screen TV. The Pool for guests of Evian is situated on a 5 acre Lagoon & 6
Hot HOT 16
Evian 240
Shipyard Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.6 (53)
70 FULL SWEEP This unique home offers an open floor plan on one floor. Plenty of privacy, directly on a lagoon, with only one neighboring house. Exterior features include a Private Pool with a Spacious Deck to sit back and enjoy all of the wildlife in the area. Easy bike ride to the beach or a 10 minute leisurely walk. Free Wi-Fi. Limit 10. Gue
Hot HOT 12
Full Sweep 70
Palmetto Dunes
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 (11)
2235 HERITAGE This 2 bedroom townhouse is the perfect location for guests who enjoy Golf, Tennis & all of the various amenities that Sea Pines has to offer. This updated villa offers a King in the master and a Queen & Bunk Bed in the 2nd bedroom. Overlooking a peaceful lagoon, with a peaceful setting where you can watch all the different birds. Gu
Hot HOT 45
Heritage Villa 2235
Sea Pines Resort Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
This villa is a spacious 2 bedroom, 2 bathroom unit located on the fourth floor, providing stunning views of the Beach, Atlantic Ocean, and Calibogue Sound. Guests can spot dolphins and shrimp boats from the beachfront living room, which is equipped with a 44" flat screen TV. The private balcony is an ideal spot for al fresco dining, with ample sea
Hot HOT 17
Beachside Tennis 1842
Sea Pines
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (26)

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