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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
Oceanfront Designer! KING BED Bar 65"TV Tennis GYM
Panoramic Oceanfront Views the moment you open the door!! ●CONDO: HGTV Featured Decorator - Luxe Coastal 100% Renovation KING BED / Expanded Bedroom! FREE: Netflix, WIFI, Cable, Phone Two 65" SmartTVs Coffee Bar Beach Chairs, Umbrella, Boogie Boards , Ice Chest, Pool Noodles Keyless Entry Designer Bath ●RESORT: Oceanfront Pool w/Tiki Bar & Grille 3 Restaurants & 2 Bars FREE: Tennis, Gym, Pickleball, Beach Volleyball & More! Bike Rentals Concierge Guarded Gate & 24 Hour Security! Bradley Beach
$178 per night
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Condo in Hilton Head Island
Ocean Front Resort Condo
Enjoy Coastal Cottage Living in a lovely 540 sq ft one bedroom vacation villa within the activity-filled gated resort of Hilton Head Beach and Tennis. Completely remodeled from with all new fixtures, furnishings, housewares and accessories, this charming beach villa has just opened its doors for guests in March 2019. Amenities include coffee, cocoa, popcorn, breakfast treats and bottled water to consume; and beach towels, chairs, umbrellas and other items to borrow while here.
$99 per night
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Condo in Hilton Head Island
BEACHFRONT KING BED VILLA, PVT BALCONY, SELF CKIN
Freshly decorated in coastal decor, this beachfront condo sleeps up to 4 and is located right by Coligny, Hilton Head's chicest neighborhood. Freshly furnished unit includes a spacious king bed and queen sofa sleeper, both fitted with luxurious memory foam mattresses. Just a three minute walk to sandy beaches, and you can catch a glimpse of gentle tides from your own private balcony! The villa is full of amenities including beach chairs, beach umbrella, games and much more.
$81 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 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 Coastal Discovery Museum
Coastal Discovery Museum101 locals recommend

Hilton Head Island beach vacation rentals

Condo in Hilton Head Island
FREE 3rd NT Dec- Feb-Beachfront-KING Bed
$69 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
OceanFront Upscale 1 Bdrm Condo/HeatedPool/Sleeps6
$128 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
Designer! KING BED Bar 65"TV Tennis GYM Oceanview!
$96 per night
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Condo in Hilton Head Island
New for 2022! Oceanview, King Bed and Bikes
$113 per night
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Condo in Hilton Head Island
FREE 3rd NT Dec- Feb OCEAN FRONT King Bed
$113 per night
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Condo in Hilton Head Island
Beach Resort-OceanView Villa-Stylish Total Remodel
$78 per night
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Condo in Hilton Head Island
⭐Oceanfront Villa•Heated Pool•South Forest Beach⭐
$130 per night
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Condo in Hilton Head Island
Ocean view! 1 bedroom beach condo
$149 per night
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Condo in Hilton Head Island
Breathtaking OCEANFRONT view/Pool/Steps to Coligny
$118 per night
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Condo in Hilton Head Island
AWESOME Retreat! King bed! Ocean View! 2 Bikes 218
$125 per night
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Hilton Head Island condo rentals

Condo in Hilton Head Island
Walk to the Beach, Pools, Hot Tub and Tennis!
$70 per night
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Condo in Hilton Head Island
Harborfront Hilton Head Condo with Sunset Views!
$94 per night
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
Ocean Front Resort Villa
$108 per night
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Condo in Hilton Head Island
Amazing Ocean View, Free Bikes and Chairs
$125 per night
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Condo in Hilton Head Island
(3)Building 1 out/indoor pool/boardwalk to beach!
$53 per night
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Condo in Hilton Head Island
Oceanview Villa, Direct Beach Access & Pool
$110 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
Hilton Head. 3 Pools/1 Indoor. Easy Beach Access.
$81 per night
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Condo in Hilton Head Island
Oceanfront Villa on Hilton Head Island 🏝
$58 per night
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Condo in Hilton Head Island
Hilton Head OCEANFRONT 💙 The Sandpiper's Nest
$231 per night
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Condo in Hilton Head Island
Couple’s Getaway | Beachfront + Walk Everywhere
$70 per night

Downtown Hilton Head Island vacation rentals

Condo in Hilton Head Island
Beautiful 2Bed, 2 Bath - Walking Beach Access
$82 per night
Condo in Hilton Head Island
Hilton Head Resort, Steps to the beach!
$111 per night
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Condo in Hilton Head Island
Clean & Fresh Condo in the Heart of Hilton Head
$59 per night
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Condo in Hilton Head Island
HHI villa, Walk to beach, 3 Pools, Indoor pool-w/d
$99 per night
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Condo in Hilton Head Island
HHR - Beach Villa (Heated Indoor Pool & Hot Tub)
$109 per night
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Condo in Hilton Head Island
Newly Remodeled Beach Condo
$119 per night
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Condo in Hilton Head Island
Shabby chic decor, chairs and bikes included
$96 per night
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Rental unit in Hilton Head Island
(1) Renovated/walk to beach from Fiddler's Cove!
$65 per night
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Condo in Hilton Head Island
Entire Beach Front Resort Condo
$109 per night
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Condo in Hilton Head Island
Newly Renovated Ocean View Villa, Hilton Head
$109 per night
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Condo in Hilton Head Island
COLIGNY! OCEAN VIEWS! 2 BIKES! 1 BDRM/1 BA #214
$102 per night
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Condo in Hilton Head Island
(4) Location! Walk to Coligny Beach Shops Dining!
$74 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.