Hilton Head Island vacation rentals

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Top-rated vacation rentals in Hilton Head Island

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Condo in Hilton Head Island
Ocean Front Resort Villa
Freshly decorated in coastal cottage decor, this 540 sq ft one bedroom villa sleeps up to 6 and is located within the activity-filled Hilton Head Beach and Tennis Resort. The villa was recently remodeled with all new kitchen, bathroom and fixtures and is just 50 steps to gorgeous beach. The views from the living room include ocean, oceanfront pool , beach bar and grill, and pond with fountain. The villa is full of amenities including beach towels, beach chairs, beach umbrella and much more.
$95 per night
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Condo in Hilton Head Island
FREE 3rd NT Dec- Feb-Beachfront-KING Bed
Message me for the free night or book it & I can adjust the rate immediately OCEAN VIEW-Amazing View-Beachfront 65” & 43” smart TV’s Beachfront-3 MIN WALK to ocean KING BED! Beautiful updates Beachfront condo. Hilton Head Island is a favorite US Island. Enjoy the tropical landscape with miles of bike trails Sleeps 4- 1 KING BED w/bunks in the same room Bunks are not TWIN SIZE but kid size. Beachfront RESORT, private beach, 2 restaurants, beachfront pool, fitness center & bike rental
$60 per night
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Villa in Hilton Head Island
Beautiful Ocean Palms Villa at the Westin Resort
Guests will enjoy Full Access to the 5 Star Westin Resort, located on the Oceanfront, with 3 Pools, Restaurants, Spa and Fitness Centre Free Daily Tennis and Golf Two Bedroom Two Bath 1350 sqft Villa Open Concept Living / Dining Large Full Kitchen / Wet Bar Wrap Around Balcony / Screened Porch with walkout to the Main Pool and Garden Big Screen Smart TV's in All Rooms Master Bedroom features King Bed Guest Bedroom can be set up as a King or Two Twin Beds Private Bathrooms for each Bedroom
$115 per night
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Vacation rentals for every style

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Stay near Hilton Head Island's top sights

Photo of Coastal Discovery Museum
Coastal Discovery Museum101 locals recommend
Photo of Shelter Cove Towne Centre
Shelter Cove Towne Centre79 locals recommend
Photo of Sea Pines Forest Preserve
Sea Pines Forest Preserve61 locals recommend
Photo of Coligny Plaza Shopping Center
Coligny Plaza Shopping Center180 locals recommend
Photo of The Sea Pines Resort
The Sea Pines Resort12 locals recommend
Photo of Harbour Town Lighthouse & Museum
Harbour Town Lighthouse & Museum124 locals recommend

Hilton Head Island beach vacation rentals

Condo in Hilton Head Island
Shelter Cove Broad Creek Beauty, sunrise, sunset
$99 per night
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Townhouse in Hilton Head Island
124 Windward Village - 2 BR/2BA Townhouse -Shipyar
$100 per night
Condo in Hilton Head Island
Ocean Palm Villa - Free Golf! Short walk to Beach!
$131 per night
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Condo in Hilton Head Island
⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐
$109 per night
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Townhouse in Hilton Head Island
Greens Villa #108 - 2 bedrooms Near Ocean
$100 per night
Condo in Hilton Head Island
Luxury First Floor Villa Free Tennis & Golf Daily
$160 per night
Condo in Hilton Head Island
Ocean Front Resort Condo
$83 per night
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Condo in Hilton Head
Relax on the Beach at Seawatch - 2 Bedroom Condo!
$134 per night
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Villa in Hilton Head Island
Ocean Palms Luxury Villa Free Daily Tennis & Golf
$154 per night
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Townhouse in Hilton Head Island
Hilton Head Beach Club - 3 Bedroom w/ a private pa
$110 per night
Condo in Hilton Head Island
Harborfront Hilton Head Condo with Sunset Views!
$94 per night
Condo in Hilton Head Island
Beachwalk 174 - Shipyard 3BR/3.5 BA Townhouse
$125 per night

Hilton Head Island condo rentals

Condo in Hilton Head Island
Oceanfront Designer! 65"TV BAR! Tennis+GYM Netflix
$98 per night
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Private room in Hilton Head Island
Located in the South Forest Beach area, HHI, SC.
$54 per night
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Condo in Hilton Head Island
*Slashed Prices* - Amazing ocean view villa
$97 per night
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Condo in Hilton Head Island
Largest villa on Hilton Head Island
$185 per night
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Condo in Hilton Head Island
A great value! Beach just steps away Hilton Head
$120 per night
Condo in Hilton Head Island
Oceanfront Designer! KING Bed 65"TV BAR Tennis GYM
$146 per night
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Condo in Hilton Head Island
Beach condo with pool and stunning nature views
$86 per night
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Condo in Hilton Head Island
Designer KING BED! BAR Tennis GYM Ocean View Patio
$86 per night
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Condo in Hilton Head Island
Ocean Overlook - The Ultimate Vacation Experience
$133 per night
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Condo in Hilton Head Island
Special Place, Relax & Unwind Near Beautiful Beach
$112 per night
Condo in Hilton Head Island
* CORAL REEF 2 BEDROOM CONDO HILTON HEAD
$97 per night
Condo in Hilton Head Island
Beach Resort-OceanView Villa-Stylish Total Remodel
$85 per night
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Hilton Head Island house rentals

Home in Hilton Head Island
Luxe Treetop Escape w/ Fire Pit & Ocean Views!
$279 per night
Home in Hilton Head Island
Ocean View "Siren's Lookout" Treehouse
$395 per night
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Home in Saint Helena Island
The Tidewatch: Beachfront Retreat on Harbor Island
$187 per night
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Home in Hilton Head Island
Harbour Town Treehouse/Sea Pines-Calibogue Lookout
$350 per night
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Home in Hilton Head Island
Sycamore at the Sound — live like a local!
$199 per night
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Home in Hilton Head Island
Private Beach Cottage, Bridal Cottage, Beach Lawn
$471 per night
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Home in Hilton Head Island
Wonderful Island's Retreat (With Private Pool)
$290 per night
Home in Hilton Head Island
Airy Treehouse w/ Bikes; Walk to Harbour Town!
$258 per night
Home in Hilton Head Island
Beach House, Heated Pool, Elevator, Walk To Beach, Fire Pit
$172 per night
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Home in South Beach
Hilton Head 22 Black Skimmer Rd Oceanfront
$850 per night
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Home in Hilton Head Island
*Cozy Deer Island near Harbor Town*
$121 per night
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Home in Hilton Head Island
Only 2 Blocks from the Beach and Coligny Plaza!!
$199 per night

Your guide to Hilton Head Island

All About Hilton Head

There are 24 golf courses and 12 miles of soft-sand beaches spread over Hilton Head Island’s 25,000 acres. Add scenic walking trails, breezy, tropical weather, and an obsession with tennis and there’s a good chance you’re here to recreate and relax. This is an island of swaying palms, easy resort-style living, and the Southern flare for hospitality for which this neck of the woods is known. Hilton Head Island is also steeped in history, with a prominent Gullah-Geechee influence that infuses this little corner of the lowcountry with a cultural richness. There are also restaurants serving traditional Southern fare, oyster shucking stalls, and folk music and artisan wares steeped in West African tradition. With so much layered history everywhere you look, you may have come here to play, but you’ll likely leave having learned a lot too.


When is the best time to stay in a vacation rental in Hilton Head Island?

If you want to visit Hilton Head Island at its busiest and most lively time of year, come during the high summer months of June, July, and August. A golf tournament every spring draws throngs of visitors, but otherwise April and May tend to be quieter times to enjoy the calmer side of island life. Visiting in September or October will also mean mild weather and few crowds, though be careful to check the hurricane forecast as tropical storms can hit in late-autumn. The Island quiets down throughout the winter, and if you choose to come at this time of year, you may just find yourself with a 25,000 acre private island resort at your fingertips — though know that it won’t be the best time for swimming in the ocean.


What are the top things to do in Hilton Head Island?

Learn about Gullah culture

The Gullah-Geechee people of Hilton Head and the surrounding lowcountry are the descendants of enslaved West Africans who, due to the remoteness of their island plantations, managed to preserve their heritage and cultural identity throughout the centuries. Take a boat tour along the waterways that link these island communities, go on a trail walk led by a Gullah elder, or savor Gullah culture in one of the best ways possible — by tasting its influence on so much of Southern cuisine.

Golf

With two dozen golf courses on Hilton Head Island, you can rest assured that this is an excellent place to putt. The island is something of a pilgrimage site for golf aficionados, with the pros and fans alike coming down every year for the regular pro tours and annual tournaments. Note that some of the island’s golf clubs are private or membership only, but fear not, there are still more than 15 public courses that anybody can enjoy.

Sea Pines Forest Preserve

Sea Pines Forest Preserve is a haven of natural beauty, wildlife, and history. Wander along wetland boardwalks, hike through forest trails, and watch alligators bask in the marshes. While here, don’t miss the 4,000-year-old Sea Pines Shell Ring, an important indigenous archeological site, and leave some time to get lost in the secret forest, past a vanishing swamp.