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Hilton Head Island vacation rentals

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Top-rated vacation rentals in Hilton Head Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Condo in Hilton Head Island
100% NEW Oceanfront Designer! KING BED 75"TV 2Bars
PANORAMIC OCEANFRONT VIEWS THE MOMENT YOU OPEN THE DOOR! 100% New Luxury Renovation 2023 by HGTV Featured Decorator! KING BED 75" SmartTV + 65" SmartTV FREE: NETFLIX,PRIME, WIFI,CABLE SPA BATH Coastal Décor Beach Chairs, Umbrella, Boogie Boards, Ice Chest Coffee Bar TOP FLOOR RESORT: No Resort Fees Beachfront Pool w/Tiki Bar & Grille 3 Restaurants & 2 Bars FREE: Tennis, Gym, Pickleball, Basketball, Volleyball & More Bike Rental Concierge Guard Gate 24 Hour Security Trolley Stop Bradley Beach
$292 per night
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Condo in Hilton Head Island
Beach Resort-OceanView Villa-Stylish Total Remodel
FULLY REMODELED OCEAN VIEW VILLA Located in Hilton Head Beach & Tennis Resort, this beautiful 540 Square foot Villa is perfect for a small family or couple looking for a relaxing and fun getaway. The second floor balcony offers a view of both the ocean and pool, as well as, offering the soothing sounds of the ocean waves Located within a gated community and with access to the beach just steps away. The resort also features 2 private pools, 3 restaurants, bike rentals, a private gym & more!
$199 per night
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Condo in Hilton Head Island
Designer Oceanfront! KING BED 65"TV Bar Tennis GYM
PANORAMIC OCEANFRONT VIEWS THE MOMENT YOU OPEN THE DOOR! Luxury 100% Renovation by HGTV Featured Decorator! Coastal Décor (2) 65" SmartTVs KING BED FREE: NETFLIX, PRIME, WIFI, CABLE Expanded Bedroom Coffee Bar Full Kitchen Beach Chairs, Umbrella, Boogie Boards , Ice Chest, Pool Noodles Spa Bath RESORT: Beachfront Pool w/Tiki Bar & Grille! 3 Restaurants & 2 Bars FREE: Tennis, Gym, Pickleball, Beach Volleyball & More Bike Rentals Concierge Guarded Gate & 24 Hour Security on Bradley Beach
$378 per night
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Stay near Hilton Head Island's top sights

Photo of Coligny Beach Park
Coligny Beach Park117 locals recommend
Photo of Coligny Plaza Shopping Center
Coligny Plaza Shopping Center180 locals recommend
Photo of Tanger Outlets Hilton Head
Tanger Outlets Hilton Head150 locals recommend
Photo of The Salty Dog Cafe
The Salty Dog Cafe120 locals recommend
Photo of Hilton Head Island Beach & Tennis Resort
Hilton Head Island Beach & Tennis Resort10 locals recommend
Photo of Shelter Cove Towne Centre
Shelter Cove Towne Centre79 locals recommend

Hilton Head Island beach vacation rentals

Rental unit in Hilton Head Island
(1) Renovated/walk to beach from Fiddler's Cove!
$125 per night
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Condo in Hilton Head Island
Ocean Overlook II - The Penthouse Experience
$413 per night
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Condo in Hilton Head Island
Breathtaking OCEAN view/Top Floor/Pool/Coligny
$334 per night
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Condo in Hilton Head Island
Newly remodeled! Stylish HHBT condo - ocean view!
$221 per night
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Condo in Hilton Head Island
Sunny, Fresh, Beach Retreat 3 min walk to the sand
$275 per night
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Condo in Hilton Head Island
Newly Remodeled Beach Condo
$192 per night
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Condo in Hilton Head Island
⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐
$290 per night
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Condo in Hilton Head Island
Beachfront Resort- KING Bed-Partial Ocean View
$168 per night
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Condo in Hilton Head Island
OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6
$260 per night
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Condo in Hilton Head Island
New for 2022! Oceanview, King Bed and Bikes
$253 per night
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Condo in Hilton Head Island
(7) Location!- walk to beach and shops @ Coligny!
$182 per night
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Condo in Hilton Head Island
BEACHFRONT KING BED VILLA, PVT BALCONY, SELF CKIN
$183 per night
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Downtown Hilton Head Island vacation rentals

Condo in Hilton Head Island
Lovely 2-bedroom Condo with pool
$158 per night
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Condo in Hilton Head Island
Stylish Remodeled Ocean View Villa at Seaside
$217 per night
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Condo in Hilton Head Island
Ocean Front Resort Villa
$149 per night
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Condo in Hilton Head Island
Elegant couples retreat - 2021 remodel oceanview!
$207 per night
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Condo in Hilton Head Island
(2) Renovated, beachfront complex w/3 restaurants!
$210 per night
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Condo in Hilton Head Island
Oceanview Designer! KING BED 65"TV Bar Tennis GYM
$270 per night
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Condo in Hilton Head Island
3 min walk to Folly Field Beach Modern & Fun 1bdrm
$207 per night
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Condo in Hilton Head Island
(5) Location! Walk to Coligny Beach Shops Dining!
$200 per night
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Condo in Hilton Head Island
Beach Escape w/ Multi Sleeping Arrangements
$154 per night
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Condo in Hilton Head Island
Hilton Head Beach & Tennis Resort Ocean View!
$269 per night
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Condo in Hilton Head Island
Hilton Head. 3 Pools/1 Indoor. Easy Beach Access.
$190 per night
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Condo in Hilton Head Island
Ocean Oasis! Peaceful beach villa with 2 bikes
$214 per night
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Weekend vacation rentals in Hilton Head Island

Condo in Hilton Head Island
Our Little Beach House In Hilton Head Island
$191 per night
Condo in Hilton Head Island
2BD/2BATH Villa! Near Beach! HHR Building 1!
$173 per night
Condo in Hilton Head Island
SEAS the DAY - 3 pools - boardwalk to beach
$234 per night
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Condo in Hilton Head Island
Harborfront Hilton Head Condo with Sunset Views!
$127 per night
Condo in Hilton Head Island
Just Beachy HHI, Updated and Ocean View!
$192 per night
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Condo in Hilton Head Island
Oceanside Beach Retreat
$175 per night
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Villa in Hilton Head Island
OCEAN VIEW VILLA...75 yards to the beach
$130 per night
Condo in Hilton Head Island
(3)Building 1 out/indoor pool/boardwalk to beach!
$155 per night
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Condo in Hilton Head Island
Hilton Head OCEANFRONT 💙 The Sandpiper's Nest
$405 per night
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Condo in Hilton Head Island
Entire Beach Front Resort Condo
$175 per night
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Condo in Hilton Head Island
Amazing Ocean View, Free Bikes and Chairs
$233 per night
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Condo in Hilton Head Island
Walk The Beach In Our Updated Resort Condo
$138 per night
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Stays in Sea Pines

Condo in Hilton Head Island
5 Star Location & Property: Walk to the Lighthouse
$217 per night
Home in Hilton Head Island
Harbour Town Treehouse/Sea Pines-Calibogue Lookout
$364 per night
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Condo in Hilton Head Island
Harbour Town Paradise! Amazing Sunset Views
$263 per night
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Condo in Hilton Head Island
Beach condo: Heated POOL! FREE early check-in!
$368 per night
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Stays in Palmetto Dunes

Condo in Hilton Head Island
Ocean Views at Villamare, Steps to the Beach!
$599 per night
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Condo in Hilton Head Island
SuiteLife @ 1208 Villamare • Ocean Views • Pools
$695 per night
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Vacation home in Hilton Head Island
Lovely Lagoon View in Palmetto Dunes Two Bedroom
$214 per night
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Condo in Hilton Head Island
Villamare Villa w/ Pool Access & Beautiful Views!
$250 per night

Stays in Harbour Town

Condo in Hilton Head Island
Heart of Harbour Town - Beach | Pool | Golf | 2BR/2.5BA - Pool Access
$267 per night
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Home in Hilton Head Island
Luxury Harbour Town Treehouse on Deer Island
$383 per night
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Condo in Hilton Head Island
1 BR/1 BA 1st Floor/King Bed/Sofa Bed/Heated Pool
$231 per night
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Rental unit in Hilton Head Island
Harbour Town Gem
$214 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.