When is the best time to visit Shipyard Plantation, Hilton Head Island, SC?

Shipyard Plantation, Hilton Head Island is most affordable and least crowded in the shoulder seasons, late spring (April-May) and early fall (September-October). Summer is peak for beach activity but rates are 30-60% higher. Off-season (November-March) offers the quietest stays and sometimes the most character.

How are the waterfront rentals in Shipyard Plantation, Hilton Head Island chosen?

Each property in Shipyard Plantation, Hilton Head Island is hand-picked for genuine waterfront access, not water view, not a short walk from the beach, but doors-to-water. Listings are selected from public booking platforms (Vrbo, Airbnb, Booking.com, Whimstay) for genuine waterfront access and accurate location. Rates are set by the host and visible at the booking link.

Are the properties on SleepByTheBeach available on Vrbo or Airbnb?

Yes, each property links directly to its listing on Vrbo, Airbnb, Booking.com, Whimstay, or the host's own booking system. We curate from public listings; we don't own or manage these properties. We may earn a small commission when you book through our affiliate links at no cost to you.

What makes Shipyard Plantation, Hilton Head Island different from other beach towns?

Curated rentals in Shipyard Plantation. It has the character of a small coastal town without the density of major resort destinations. Our curation focuses on quiet, authentic stays within walking distance of the water.

Shipyard Plantation, Hilton Head Island

Curated rentals in Shipyard Plantation

See the 3 waterfront rentals → Get the weekly letter

4923 waterfront rentals·10 shores·Every listing on the water·Updated 2026-10-15

Hilton Head's foot-shaped barrier island sits just across the Georgia line. Gated plantation communities (Sea Pines, Palmetto Dunes, Shipyard) house most luxury rentals. Golf is everywhere, the beach is firm enough to bike, and October is the sweet spot for weather plus price.

StateSC

Peak seasonJune to August

Best forWaterfront stays

Featured3 rentals

The curated list · 3 rentals

Where we would stay in Shipyard Plantation, Hilton Head Island.

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No. 01

Shipmaster Villa 801 - Perfect Beach and Golf

Condo

2 bedroom sleeps 6 private pool

Beach, Pool, Golf! This lovely Shipyard villa has it all!!! Nothing beats a day in the sun and sand, start planning your trip now! Shipyard Oceanfront Resort 2 Bedroom 2.5 Bathroom Villa which includes 3 premier golf courses for a golf vacation, Van de Meer Tennis for the tennis player, Shipyard Beach Club and the Sonesta Hotel. Shipyard has it all for your perfect beach vacation Stay within Shipyard Plantation ocean front resort in a 2 Bedroom 2.5 Bathroom villa with 2 master bedrooms and private baths overlooking the golf course, one of Hilton Head's premier gated communities. This roomy private end unit villa has the space for your group to relax.

Check rates on Whimstay →

No. 02

Splendid condo, pool, full kitchen, & patio

Condo

2 bedroom sleeps 6 private pool

Greens 153 Nestled within the exclusive Shipyard Plantation in Hilton Head, SC, The Greens condominiums offer a serene retreat for your vacation getaway. Just a short two and a half blocks from the Atlantic Ocean, the Sonesta Oceanfront resort, and the Van der Meer Tennis Academy, this condo provides the perfect location for beach lovers and sports enthusiasts alike. Step inside this spacious condo to discover a beautifully upgraded kitchen featuring granite countertops and stainless steel appliances, perfect for preparing meals during your stay. The open layout creates a welcoming atmosphere, ideal for relaxing after a day of exploring all that Hilton Head has to offer.

Check rates on Whimstay →

No. 03

Spacious condo with pool, tennis courts, & golf on-site

Condo

1 bedroom sleeps 4 private pool

Greens 204 The Greens condominiums are within Shipyard Plantation, a private residential and resort community with many biking and walking paths. The complex encompasses two and a half blocks of the Atlantic Ocean, the Sonesta oceanfront resort, and the Van der Meer Tennis Academy. The condo offers a spacious layout, an upgraded kitchen with granite and stainless steel appliances, plus all-new carpets, tile, new wood laminate, furniture, new bathroom vanities, and new drapes. This home is beautiful and has all the comforts you expect including two flat-screen TVs and free WiFi.

Check rates on Whimstay →

Search every stay in Shipyard Plantation, Hilton Head Island on Booking.com

Hotels, beach houses, apartments, and resorts. Free cancellation on most rooms. Then add a flight in or a rental car for dune drives.

Search stays → Flights to Shipyard Plantation, Hilton Head Island Car rental

Or browse the same coast on Vrbo:

Browse Vrbo →

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Curated luxury alternative

Prefer a boutique hotel or villa?

If a hand-picked, design-led hotel sounds better than a vacation rental, Skylark Travel Group covers the same destinations with curated boutique stays, Mr & Mrs Smith, exclusive deals, real human concierge.

Discover Skylark → See exclusive deals

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Hand-picked for genuine waterfront. New finds and off-season picks, sent when there is something worth sending. No spam.