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Hilton Head Romantic Vacation Rentals

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769 rentals in Hilton Head.
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Oceanfront Resort: Clean and Comfortable: Walk to the beach
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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Hilton Head Resort, Family Friendly, Beautiful Beaches, Great Ammenities
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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3406 Resort Condo - Beach, 3 Pools, Hot Tub, Sauna, Tennis, Restaurants, Fitness
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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RELAX or HAVE FUN: 2 bed condo (walk to beach)
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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2BR Beach Escape and Condo at Hilton Head
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Spacious Palmetto Dunes Home on Golf Course
Rental Home
7 bedrooms
7 bathrooms
Sleeps 23
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Cozy 2 BR 2 bath Villa, Walk to beach, tennis courts, pool
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Just Remodeled! Oceanfront 43 Ocean Club Villa. Pool, Free Bikes, WiFi,
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Ocean One 422 - Beachside 4th Floor Condo
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
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2-Bed, 2-Bath. Short Walk to Private Beach access and pool.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Memorable - 2 Master Suites, On The Harbour Town Golf Course, Large Shady Yard,
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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Courtside 110 - Townhouse -3 Bedroom Short Walk to the Beach
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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1BR Seaside Villas 2nd Floor Condo with Ocean and Pool View
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Book Your Summer Stay! Oceanfront Villa!
Rental Home
1 bedroom
1 bathroom
Sleeps 6
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Sea Pines Plantation Club Villa #443 - Great Location!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Beachside Resort-Indoor/Outdoor Pools/Tennis/Hot Tub/WIFI
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 7
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Hilton Head Island Sea Pines villa with nearest access to beach and golf cbeach
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Shorewood 202 - Direct Oceanfront Beautiful Condo!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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Steps away from the BEACH!!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
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Courtside 61- 2 bedroom - Ground Floor - Pool View - Free Tennis
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
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53 Springwood Villas - 2 bedroom Coligny Townhouse
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Ocean Villa on Hilton Head Island, SC - Steps from the beach and pool.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Springwood 44 - 2 bedroom Townhouse
Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
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23 Dune - Mimi's Place - Private Beach Access, Large Pool, Giant Pool Deck
Rental Home
7 bedrooms
7 bathrooms
Sleeps 19
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Gorgeous Forest Beach Villa - surf & sand just steps to the beach!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Breakers 110 - 1st Floor Updated Ocean Front
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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49 Dune Lane - Sweet Carolina, 8 Bedroom Oceanfront
Rental Home
8 bedrooms
9 bathrooms
Sleeps 26
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2 bed/2 bath Hilton Head Resort Ocean Villa-Best Location in Hilton Head Resort
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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35 Dune Lane - Southern Comfort
Rental Home
7 bedrooms
8 bathrooms
Sleeps 22
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117 Dune Lane - Spectacular Oceanfront Beach Home with Large Pool
Rental Home
6 bedrooms
5 bathrooms
Sleeps 16
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47 Dune Lane - My Sunshine, Oceanfront 5 Bedroom, North Forest Beach
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
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220 Forest Beach Villas - 2 bedroom, near Coligny Condo across from the beach!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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182 Beachwalk - Shipyard Condo, 7 minutes to the beach
Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
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43 Dune Lane - 7 Bedroom, 2nd Row Home
Rental Home
7 bedrooms
7 bathrooms
Sleeps 16
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17 Heron Street - 200 Feet to the Beach!
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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6 Quail - Pet Friendly 6 Bedroom, 3rd Row from the Beach
Rental Home
6 bedrooms
5 bathrooms
Sleeps 19
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Spectacular Home with Brand New Pool in Harbour Town! Rare December cancellation
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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Charming 3 Br Home, Private Pool And Dock On Serene Lagoon In Palmetto Dunes.
Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
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5 Star Ratings - Ocean View - South Beach Marina
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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2 Min Walk 2 Beach, Golf, Tennis, Pickleball, Pvt Heated Pool, SPA, Bikes, Kayak
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
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Adorably furnished and renovated Ocean Villa condo with upgrades galore!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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3 BR w/Direct Ocean Front View; Don't Wait! Only 2 Spring/Summer Weeks Left!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Stylishly Renovated Villa With Fabulous Views and All Amenities
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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Ocean Dunes 318-***Sale Next Week/Very Contemporary/Million Dollar View/2Bikes
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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3rd Row On Beach Path...Steps to Ocean! Major Renovations Just Completed!
Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
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Awesome Ocean View - Beautifully Remodeled - Relax at the Beach!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Luxury Oceanfront Penthouse 2018 Total Remodel Done! Breathtaking Views!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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20 % OFF - Harbour Cove - Remodeled Luxury Steps from Lighthouse in HarbourTown
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
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Closest Villamare Condo to the Beach! With Extra Large Living Area
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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5/5 Rated, Premier Partner villa awaits your arrival!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Hilton Head Island Vacation Rentals and Beach Condos
“A golfer’s paradise.” That’s what Hilton Head Island is often called, with its 24 championship courses and beautiful year round weather. But stay a week in one of its breezy beach rentals or condo rentals and you’ll quickly realize there’s more to this Southern oasis than golf. Only 12 miles by five miles wide, Hilton Head’s sparkling sandy shoreline is considered one of the best family beaches in the United States. Beach rentals provide amazing water activities and outdoor recreation for families and friends of all ages. Gorgeous condo rentals inland offer a plethora of land pursuits for the energetic and sporty vacationer.
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Hilton Head Island Vacation Rentals and Beach Condos
“A golfer’s paradise.” That’s what Hilton Head Island is often called, with its 24 championship courses and beautiful year round weather. But stay a week in one of its breezy beach rentals or condo rentals and you’ll quickly realize there’s more to this Southern oasis than golf. Only 12 miles by five miles wide, Hilton Head’s sparkling sandy shoreline is considered one of the best family beaches in the United States. Beach rentals provide amazing water activities and outdoor recreation for families and friends of all ages. Gorgeous condo rentals inland offer a plethora of land pursuits for the energetic and sporty vacationer.
The Ultimate Family Vacation Starts on Hilton Head Island
Spacious vacation rentals – from beachfront villas and traditional country homes to airy summer chateaus – make Hilton Head Island the ideal family getaway. With mini golf at Pirate’s Island and Adventure Cove, the grown-ups aren’t the only ones hitting the links. Condo rentals on the south end of Hilton Head are minutes from The Sandbox, An Interactive Children’s Museum, offering educational play between kids and parents, like the Rhythm and Hues painting exhibit. Give the little ones a break from the sun at the indoor Island Playground, complete with inflatable slides, obstacle courses and a toddler exploration area.
Hilton Head Island Attractions For Adults
Vacation rentals on Hilton Head Island also offer incredible attractions for adults and older children. Venture inland for miles of paved bike paths leading down gorgeous scenic trails. Fly along ziplines over magnificent live oaks and gaze at the boats, bogs and bottlenose dolphins residing in Broad Creek Marina. The wildlife outside your condo rental is vast and exquisite. Take a Hilton Head forest hayride to see bobcats, minks, deer, otters and eclectic species of birds, or hit the petting zoo and horseback tours at Lawton Stables.
Experience Cuisine, Nightlife and Spirits Like Never Before
Vacation rentals on Hilton Head Island offer a social scene that families or couples will love. The island boasts over 250 restaurants and authentic cuisine. Hudson’s Seafood House on the docks is Hilton Head’s oldest establishment, serving up the freshest of oceanic chow with astounding views of the Intracoastal Waterway. Enjoy a romantic night under the starry skies at WiseGuys, a local see-and-be-seen hotspot with an award-winning wine list. Get your southern barbecue fix from The Smokehouse, plating local favorites like Gullah rice, gumbo, fried okra and delectable peach cobbler.
Vacation Rentals on Hilton Head Island Are Can’t-Miss
Enjoy numerous recreational activities or just relax on the pristine beaches of Hilton Head Island. TripAdvisor is the only place for the best deals on beach rentals, condos, vacation homes and more.