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.
$100 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
$63 per night
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Condo in Hilton Head Island
FREE 3rd NT Dec- Feb OCEAN FRONT King Bed
Gorgeous remodel! THIRD NIGHT FREE is offered DEC-FEB for CONSECUTIVE nights only Message me & I'll send the rate adjustment as a special offer or book 3 NTS & and I will immediately adjust the rate OCEAN BEACHFRONT RESORT 3 MIN WALK to beachfront Beachfront pool Tropical bike paths throughout island offer amazing views King Bed w/ kid size bunks (not twin size) in the same room. A non-locking door separates the living room sleeping area from the King Bed & bunks Max 4 ADULTS/2 kids
$69 per night
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Stay near Hilton Head Island's top sights

Photo of Coligny Plaza Shopping Center
Coligny Plaza Shopping Center180 locals recommend
Photo of Shelter Cove Towne Centre
Shelter Cove Towne Centre79 locals recommend
Photo of Tanger Outlets Hilton Head
Tanger Outlets Hilton Head150 locals recommend
Photo of The Sea Pines Resort
The Sea Pines Resort12 locals recommend
Photo of Fish Haul Beach Park
Fish Haul Beach Park34 locals recommend
Photo of Coastal Discovery Museum
Coastal Discovery Museum101 locals recommend

Hilton Head Island beach vacation rentals

Condo in Hilton Head Island
Oceanview Designer! KING BED Bar! 65"TV Tennis GYM
$89 per night
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Condo in Hilton Head Island
Newly remodeled! Stylish HHBT condo - ocean view!
$78 per night
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Condo in Hilton Head Island
BEACHFRONT KING BED VILLA, PVT BALCONY, SELF CKIN
$85 per night
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Condo in Hilton Head Island
Ocean view! 1 bedroom beach condo
$93 per night
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Condo in Hilton Head Island
OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6
$130 per night
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Condo in Hilton Head Island
New for 2022! Oceanview, King Bed and Bikes
$117 per night
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Condo in Hilton Head Island
The Breakers- Direct Oceanfront
$150 per night
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Condo in Hilton Head Island
2BD/2BATH Villa! Near Beach! HHR Building 3!
$72 per night
Condo in Hilton Head Island
⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐
$114 per night
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Condo in Hilton Head Island
Beach Resort-OceanView Villa-Stylish Total Remodel
$74 per night
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Condo in Hilton Head Island
Breathtaking OCEANFRONT view/Pool/Steps to Coligny
$110 per night
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Condo in Hilton Head Island
Harborfront Hilton Head Condo with Sunset Views!
$94 per night

Hilton Head Island condo rentals

Condo in Hilton Head Island
Walk to the Beach, Pools, Hot Tub and Tennis!
$66 per night
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Condo in Hilton Head Island
AWESOME Retreat! King bed! Ocean View! 2 Bikes 218
$145 per night
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Condo in Hilton Head Island
Ocean Front Resort Condo
$99 per night
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Condo in Hilton Head Island
Amazing Ocean View, Free Bikes and Chairs
$112 per night
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Condo in Hilton Head Island
Hilton Head. 3 Pools/1 Indoor. Easy Beach Access.
$101 per night
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Condo in Hilton Head Island
(3)Building 1 out/indoor pool/boardwalk to beach!
$63 per night
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Condo in Hilton Head Island
High End Condo! CLEAN! Ocean View~2 Bikes! #109
$105 per night
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Condo in Hilton Head Island
Oceanfront Villa on Hilton Head Island 🏝
$57 per night
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Condo in Hilton Head Island
2BD/2BATH Villa! Near Beach! HHR Building 1!
$72 per night
Condo in Hilton Head Island
2BD/2BATH Villa! Near Beach! HHR Building 4!
$72 per night
Condo in Hilton Head Island
Hilton Head OCEANFRONT 💙 The Sandpiper's Nest
$229 per night
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Condo in Hilton Head Island
Hilton Head Resort, Steps to the beach!
$125 per night
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Downtown Hilton Head Island vacation rentals

Rental unit in Hilton Head Island
Newly Renovated 1 Bedroom/1 Bath Condo w/Sofa Bed
$99 per night
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Condo in Hilton Head Island
Beautiful 2Bed, 2 Bath - Walking Beach Access
$82 per night
Condo in Hilton Head Island
Couple’s Getaway | Beachfront + Walk Everywhere
$66 per night
Condo in Hilton Head Island
Direct Ocean View Seaside Villas
$184 per night
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Condo in Hilton Head Island
Newly Remodeled Beach Condo
$108 per night
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Condo in Hilton Head Island
Beach Views, Hilton Head Beach Condo
$107 per night
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Condo in Hilton Head Island
(4) Location! Walk to Coligny Beach Shops Dining!
$68 per night
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Condo in Hilton Head Island
Walk To The Beach! 3 Pools, Tennis/Pickleball
$89 per night
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Condo in Hilton Head Island
Entire Beach Front Resort Condo
$96 per night
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Condo in Hilton Head Island
Newly Renovated Ocean View Villa, Hilton Head
$110 per night
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Condo in Hilton Head Island
Hilton Head BIKE 'n BED - Perfect Couple's Getaway
$111 per night
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Condo in Hilton Head Island
Cozy Renovated Unit Great Location
$89 per night
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Stays in Sea Pines

Vacation home in Hilton Head Island
Sealoft in Sea Pines-Water Views 2033 Deer Island
$153 per night
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Condo in Hilton Head
Villa w/ Golf Course Views, Walk to Harbour Town!
$119 per night
Home in Hilton Head Island
Luxe Treetop Escape w/ Fire Pit & Ocean Views!
$279 per night
Condo in Hilton Head Island
Stunning Sea Pines Treetop Oasis | Deck & Grill | Half-Mile to Harbour Town
$131 per night

Stays in Palmetto Dunes

Cottage in Hilton Head Island
Gypsy Sea Cottage - A Seaside Retreat
$117 per night
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Condo in Hilton Head Island
Ocean Views at Villamare, Steps to the Beach!
$250 per night
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Condo in Hilton Head Island
Hilton Head Oceanfront-Captains Walk
$232 per night
Condo in Hilton Head Island
Ocean Overlook II - The Penthouse Experience
$129 per night
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Stays in Harbour Town

Home in Hilton Head Island
Peaceful Harbour Town Treehouse with Marsh Views
$213 per night
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Condo in Hilton Head Island
1 BR/1 BA 1st Floor/King Bed/Sofa Bed/Heated Pool
$99 per night
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Condo in Hilton Head Island
Hilton Head Island Getaway in Harbour Town!
$150 per night
Condo in Hilton Head Island
Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access
$107 per night
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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.