Monthly Vacation Guide - May 2026

Monthly Vacation Guide - May 2026

Hilton Head Island is a destination for all seasons! But this month is looking better than ever here on our beautiful barrier island. Hilton Head is nestled on the southern tip of the South Carolina coastline with a sub-tropical climate, an average of 215 sunny days a year, and mild temps to enjoy our pristine beaches, serene waterways, untouched nature preserves and award-winning golf and tennis facilities year round. 

Every month brings new experiences, unique adventures, seasonal events and laid-back Lowcountry living on Hilton Head. Check out this monthly vacation guide to help plan your trip this month while traveling to our little slice of paradise.


THINGS TO DO 

1. Music & Taste on the Harbour - Enjoy live music from local bands and savor seasonal appetizers on the waterfront at Shelter Cove Harbour on May 7th and 14th.

2. Hilton Head Art Festival - Stroll through Shelter Cove from May 22nd - 24th for the Hilton Head Art Festival, featuring a vibrant collection of handmade crafts and live local music.

3. Paddle Through Local Waters - Paddle through the island's scenic salt marshes this May, as the calm spring waters and mild breezes offer the perfect setting for a peaceful excursion.


PLACES TO EAT 

1. Harbourside - Savor fresh crab legs and signature frozen cocktails at Harbourside, with an open-air patio, live music, and views of the iconic lighthouse.

2. Java Burrito Company - Stop by Java Burrito for fresh, made-to-order burritos using locally sourced ingredients, paired with a full-service craft coffee bar.

3. Coco's On The Beach - Head to Coco’s on the Beach for fresh margaritas and Caribbean vibes in a colorful shack with island music and ocean views in a casual, barefoot setting.


WHERE TO STAY 

1. Gunnery Lane 4 - This five bedroom Sea Pines home offers bright, open interiors with plenty of natural light, a private pool, and plenty of room for the whole family.

2. Hilton Head Resorts 2320 (Pictured) - This two bedroom condo features a fresh open layout, coastal decor, and a convenient location near the resort pools and beach.

3. Colonnade Club 159 - This three bedroom condo boasts golf course and lagoon views from a private patio, access to a sparkling community pool, and spacious interiors.


The most important factor in planning for your Hilton Head vacation is finding a home away from home.

Sunset Rentals has been proudly serving guests on the island for more than 25 years – come and experience the Sunset Advantage on Hilton Head!

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