Hilton Head Island Vacation Rentals

Hilton Head Island Vacation Rentals & Vacation Homes!

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These Hilton Head Island vacation homes, condos, villas, cabins, cottages, chalets, and bed & breakfasts are presented by their owners or agents. Please contact them directly with your inquiries. Click on the underlined descriptions below for more details and property photos.

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City  Bedrooms
Weekly Rate  Interests 

  Preferred Listings
Sea Pines Plantation Private 4 Bedroom Vacation Home Rental - managed by "Hilton Head Luxury Rentals"
  • Sea Pines
  • House (single)
  • 4 bedrooms, sleeps 10
  • 3 bathrooms
  • Weekly rates
    From $2,195 to $4,995 USD
 

3 Black Duck
5 Bedroom, 5.5 Bath
2nd Row Private Home
Sea Pines Plantation - managed by "Hilton Head Luxury Rentals"
  • Sea Pines
  • House (single)
  • 5 bedrooms, sleeps 12
  • 5.5 bathrooms
  • Weekly rates
    From $514 to $6,300 USD
 

Shelter Cove is part of Prestigious Palmetto Dunes Resort - 3 Deluxe Condo Styles
  • Palmetto Dunes
  • Condo
  • 2 bedrooms, sleeps 6
  • 2 bathrooms
     

    Seascape #3222 - Hilton Head Island
    • South Forest Beach
    • Villa
    • 3 bedrooms
    • 2 bathrooms
       

      Sea Pines 5 Bedroom Oceanfront Home with Pool
      • Sea Pines
      • Villa
      • 5 bedrooms, sleeps 14
      • 4 bathrooms
      • Weekly rates
        From $3,950 to $7,900 USD
       

      Oceanfront 5 Bedroom Home w ith Private Pool & Spa
      • Palmetto Dunes
      • House (single)
      • 5 bedrooms, sleeps 14
      • 5.5 bathrooms
         

        32 Sand Dollar
        Oceanfront Private Home
        4 Bedrooms,4 Baths
        Folly Field - managed by "Hilton Head Luxury Rentals"
        • Folly Field
        • House (single)
        • 4 bedrooms, sleeps 10
        • 4 bathrooms
        • Weekly rates
          From $428 to $5,250 USD
         

        Beautiful Ocean Views and Affordable for You - Hilton Head Island
        • Folly Field
        • Condo
        • 2 bedrooms, sleeps 6
        • 2 bathrooms
        • Weekly rates
          From $425 to $800 USD
         

        7 Bedroom Oceanview Home with Private Pool & Spa
        • Forest Beach
        • House (single)
        • 7 bedrooms, sleeps 16
        • 8 bathrooms
        • Weekly rates
          From $4,500 to $9,000 USD
         

        7th Row Ocean Home with Private Pool & Spa
        • Sea Pines
        • House (single)
        • 5 bedrooms, sleeps 12
        • 4 bathrooms
        • Weekly rates
          From $3,125 to $4,800 USD
         

        A Great Vacation Escape - Fiddler's Cove with Virtual Tours!
        • Folly Field
        • Villa
        • 2+ bedrooms, sleeps 6
        • 2 bathrooms
           

          The Surfside House - Oceanfront Including Oceanfront Pool!
          • North Forest Beach
          • House (single)
          • 5 bedrooms, sleeps 12-14+
          • 4 bathrooms
             

            Crabline 5 Bedroom Home
            Private Small Pool
            Elevator
            "Ralph Lauren" Style Decor - managed by "Hilton Head Luxury Rentals"
            • Singleton Beach
            • House (single)
            • 5 bedrooms, sleeps 12
            • 5 bathrooms
            • Weekly rates
              From $185 to $2,495 USD
             

            Golf & Pet Friendly Hilton Head Condo
            • Palmetto Dunes
            • Condo
            • 2 bedrooms, sleeps 6-8
            • 2 bathrooms
               

              The Dune House-Beautiful Oceanfront Vacation Home
              • North Forest Beach
              • House (single)
              • 6 bedrooms, sleeps 10+
              • 5 bathrooms
                 

                Halcyon Days Luxury Oceanfront Rental - Hilton Head Island
                • Forest Beach
                • House (single)
                • 8 bedrooms
                • 8.5 bathrooms
                • Weekly rates
                  From $3,950 to $13,950 USD
                 

                Hilton Head Beach & Tennis Condo - "A True Ocean Front Condo"
                • Folly Field
                • Condo
                • 1 bedrooms, sleeps 5
                • 1 bathrooms
                   

                  2BR/2½ BA, 3 Blocks from the Beach, Free Tennis & 2 Pools
                  • South Forest Beach
                  • Townhouse
                  • 2 bedrooms, sleeps 4-6
                  • 2.5 bathrooms
                     

                    6 Bedroom Oceanfront Home with Pool, Spa, Putt-Putt & Billiard Room
                    • Singleton Beach
                    • House (single)
                    • 6 bedrooms, sleeps 16
                    • 6.5 bathrooms
                       

                      5 Bedroom Oceanview Home with Private Pool & Spa
                      • Forest Beach
                      • House (single)
                      • 5 bedrooms, sleeps 14
                      • 5.5 bathrooms
                      • Weekly rates
                        From $3,125 to $6,250 USD
                       

                      5 Bedroom 2nd Row Oceanview Home with Private Pool & Spa
                      • Folly Field
                      • House (single)
                      • 5 bedrooms, sleeps 12
                      • 5.5 bathrooms
                         

                        Turnberry Villa
                        • South Forest Beach
                        • Townhouse
                        • 2 bedrooms, sleeps 4
                        • 2 bathrooms
                           

                          Hilton Head Condo at the Spa on Port Royal Sound - Best Value on the Island!
                          • Port Royal
                          • Villa
                          • 1 bedrooms, sleeps 2
                          • 1 bathrooms
                             

                            Shipyard Plantation Villa with Pool, Spa & Beach Access - Hilton Head Island
                            • Shipyard
                            • Condo
                            • 2 bedrooms, sleeps 4-6
                            • 2 bathrooms
                            • Weekly rates
                              From $560 to $875 USD
                             

                            17 Sweetgrass Manor - 2nd Row Ocean View Home
                            • Bradley Beach
                            • House (single)
                            • 6 bedrooms
                            • 7 bathrooms
                            • Weekly rates
                              From $3,250 to $6,500 USD
                             

                            Waterside by Spinnaker - Featuring the Largest Aquatic Facility on Hilton Head Island
                            • Forest Beach
                            • Resort
                            • 1-3 bedrooms
                               

                              507 Shorewood - Hilton Head Island
                              • Forest Beach
                              • Condo
                              • 3 bedrooms, sleeps 6
                              • 3 bathrooms
                              • Weekly rates
                                From $1,200 to $2,000 USD
                               

                              16 Full Sweep - Private Pool with Lagoon & Golf Views
                              • Palmetto Dunes
                              • House (single)
                              • 4 bedrooms
                              • 4.5 bathrooms
                              • Weekly rates
                                From $3,500 to $5,000 USD
                               

                              Bradley Beach - 7 Swingle Manor - 6th Row Ocean Home with Private Pool
                              • Bradley Beach
                              • House (single)
                              • 5 bedrooms, sleeps 14
                              • 5 bathrooms
                              • Weekly rates
                                From $2,500 to $5,000 USD
                               

                              HILTON HEAD ISLAND VACATION VILLA - # A2C SANDS VILLAGE
                              • Forest Beach
                              • Villa
                              • 2 bedrooms, sleeps 6
                              • 1 bathrooms
                              • Weekly rates
                                From $800 to $900 USD
                               

                              Ocean View Hilton Head Beach and Tennis Resort
                              • Hilton Head Plantation
                              • Condo
                              • 1 bedrooms
                              • Weekly rates
                                From $500 to $800 USD
                               

                               
                                Rental Locations   (Listed alphabetically by City or Town)
                               

                                City BR(s) BA(s) Sleeps Description
                              Bradley Beach 5 BR 5 BA 14 Bradley Beach - 7 Swingle Manor - 6th Row Ocean Home with Private Pool
                              Bradley Beach 5 BR 5 BA 12 Bradley Beach Oceanfrony Vacation Home with Pool & Hot Tub
                              Bradley Beach 6 BR 7 BA 17 Sweetgrass Manor - 2nd Row Ocean View Home
                              Folly Field 1 BR 1 BA 5 Hilton Head Beach & Tennis Condo - "A True Ocean Front Condo"
                              Folly Field 2 BR 2 BA 6 Bargin Rental on Hilton Head Island
                              Folly Field 2 BR 2 BA 6 Beautiful Ocean Views and Affordable for You - Hilton Head Island
                              Folly Field 2+ BR 2 BA 6 A Great Vacation Escape - Fiddler's Cove with Virtual Tours!
                              Folly Field 4 BR 4 BA 10 32 Sand Dollar
                              Oceanfront Private Home
                              4 Bedrooms,4 Baths
                              Folly Field - managed by "Hilton Head Luxury Rentals"
                              Folly Field 5 BR 5.5 BA 12 5 Bedroom 2nd Row Oceanview Home with Private Pool & Spa
                              Forest Beach 1-3 BR BA Waterside by Spinnaker - Featuring the Largest Aquatic Facility on Hilton Head Island
                              Forest Beach 1 BR 1 BA 4 Ocean Front Seaside Villas - South Forest Beach
                              Forest Beach 1 BR 1 BA 4 Oceanfront View from Private Balcony - Breakers
                              Forest Beach 2 BR 1 BA 6 HILTON HEAD ISLAND VACATION VILLA - # A2C SANDS VILLAGE
                              Forest Beach 2 BR 2.5 BA 4-7 #1 Hilton Head Location - Walk to Beach - Spotless - Pet Friendly
                              Forest Beach 3 BR 2 BA 8 Ocean Home with Private pool Secluded
                              Forest Beach 3 BR 3 BA 6 507 Shorewood - Hilton Head Island
                              Forest Beach 3 BR 2 BA 8 3 Bedroom Home Private Pool Walk to Beach
                              Forest Beach 4 BR 3.5 BA 8 4 Bedroom Home Golf View Private Pool
                              Forest Beach 4 BR 3 BA 12 Forest Beach 4 Bedroom Home with Private Pool
                              Forest Beach 5 BR 4.5 BA 12 5 Bedroom Home with Private Pool steps to the Beach!
                              Forest Beach 5 BR 5.5 BA 14 5 Bedroom Oceanview Home with Private Pool & Spa
                              Forest Beach 6 BR 6.5 BA 12 6 Bedroom Home with Private Pool & Spa
                              Forest Beach 7 BR 8 BA 16 7 Bedroom Oceanview Home with Private Pool & Spa
                              Forest Beach 8 BR 8.5 BA Halcyon Days Luxury Oceanfront Rental - Hilton Head Island
                              Hilton Head Plantation 1 BR BA Ocean View Hilton Head Beach and Tennis Resort
                              North Forest Beach 4 BR 3 BA 10 30 Pelican
                              4 Bedroom, 3 Bath
                              4th Row Private Home
                              North Forest Beach - managed by "Hilton Head Luxury Rentals"
                              North Forest Beach 4 BR 3 BA 12 Private 4 Bedroom Home
                              Private Pool
                              North Forest Beach
                              150 Feet to Beach - managed by "Hilton Head Luxury Rentals"
                              North Forest Beach 5 BR 4 BA 12-14+ The Surfside House - Oceanfront Including Oceanfront Pool!
                              North Forest Beach 6 BR 5 BA 10+ The Dune House-Beautiful Oceanfront Vacation Home
                              Palmetto Dunes 1 & 2 BR 1 & 2 BA 2-4 1 & 2 Bedroom Windsor Place Villas
                              Palmetto Dunes 2 BR 2 BA 6-8 Golf & Pet Friendly Hilton Head Condo
                              Palmetto Dunes 2 - 3 BR 2 BA 4-6 Turnberry Village
                              2 Bedroom Townhomes
                              Pet Friendly
                              Palmetto Dunes Plantation - managed by "Hilton Head Luxury Rentals"
                              Palmetto Dunes 2 - 3 BR 2 BA 8 Fazio
                              2 & 3 Bedroom Townhomes
                              Palmetto Dunes - managed by "Hilton Head Luxury Rentals"
                              Palmetto Dunes 2 BR 2 BA 8 Villamare
                              Oceanfront Property
                              1 & 2 Bedroom
                              Palmetto Dunes Plantation - managed by "Hilton Head Luxury Rentals"
                              Palmetto Dunes 2 BR 2 BA 6 Shelter Cove is part of Prestigious Palmetto Dunes Resort - 3 Deluxe Condo Styles
                              Palmetto Dunes 4 BR 4.5 BA 16 Full Sweep - Private Pool with Lagoon & Golf Views
                              Palmetto Dunes 5 BR 5.5 BA 14 Oceanfront 5 Bedroom Home w ith Private Pool & Spa
                              Port Royal 1 BR 1 BA 4-6 Hilton Head, South Carolina - Beautiful Oceanfront Condo
                              Port Royal 1 BR 1 BA 2 Hilton Head Condo at the Spa on Port Royal Sound - Best Value on the Island!
                              Port Royal 1 BR 1 BA 4-6 Beach & Tennis Resort
                              1 & 2 Bedroom Condos
                              Affordable Family Fun
                              Oceanfront Property - managed by "Hilton Head Luxury Rentals"
                              Port Royal 2 BR 2 BA 6 Hilton Head, South Carolina 2 Bedroom Oceanfront Condo
                              Sea Pines 2 BR 2 BA 6 Lighthouse Tennis Villas
                              2 Bedroom
                              Free Tennis
                              Sea Pines Plantation - managed by "Hilton Head Luxury Rentals"
                              Sea Pines 3 BR 3 BA 8 Racquet Club
                              2 & 3 Bedroom Townhomes
                              Sea Pines Plantation
                              Walk to Harbour Town - Free Tennis - managed by "Hilton Head Luxury Rentals"
                              Sea Pines 3 BR 3 BA 8-10 Sea Pines Plantation Luxury Oceanside House with Golf View - Near Beach, Free Bikes, Pool, Tennis / Pet Friendly
                              Sea Pines 3 BR 3.5 BA 8 3 Bedroom Home Golf View Private Pool near Beach
                              Sea Pines 3+ Loft BR 3.5 BA 8 Near Beach & Ocean, Lagoon View, Free Tennis, Bikes, Pool, Internet / easy bike or walk access to Harbour Town or South Beach in Sea Pines Plantation
                              Sea Pines 3 BR 3 BA 10 Sea Pines 4 Bedroom Vacation Home with Pool
                              Sea Pines 3 BR 2.5 BA Pet Friendly Sea Pines Vacation Home with Pool
                              Sea Pines 4 BR 3 BA 8 Sea Pines Plantation Vacation Home with Ocean Views - 2nd House from the Beach
                              Sea Pines 4 BR 4.5 BA 10 Sea Pines Vacation Home with Private Pool
                              Sea Pines 4 BR 3 BA 14 4 Bedroom Oceanfront Home with Private Pool & Spa
                              Sea Pines 4 BR 3 BA 10 Sea Pines Plantation Private 4 Bedroom Vacation Home Rental - managed by "Hilton Head Luxury Rentals"
                              Sea Pines 4 BR 3 BA 9 2 Rice Lane - Sea Pines with Pool
                              Sea Pines 5 BR 5.5 BA 12 3 Black Duck
                              5 Bedroom, 5.5 Bath
                              2nd Row Private Home
                              Sea Pines Plantation - managed by "Hilton Head Luxury Rentals"
                              Sea Pines 5 BR 3.5 BA 12 Sea Pines Vacation Home
                              Sea Pines 5 BR 4 BA 10 12 Grey Widgeon - 2nd Row Ocean View - Hilton Head Island
                              Sea Pines 5 BR 4 BA 14 Sea Pines 5 Bedroom Oceanfront Home with Pool
                              Sea Pines 5 BR 6 BA Private Sea Pines Plantation - managed by "Hilton Head Luxury Rentals"
                              Sea Pines 5 BR 4 BA 12 7th Row Ocean Home with Private Pool & Spa
                              Sea Pines 5 BR 4.5 BA 12 Oceanfront 5 Bedroom Home
                              Private Pool&Hot Tub
                              North Forest Beach - managed by "Hilton Head Luxury Rentals"
                              Shipyard 1 BR 2 BA 4 Beachwalk
                              1 & 2 Bedroom Condos
                              Shipyard Plantation - managed by "Hilton Head Luxury Rentals"
                              Shipyard 1 BR 1 BA 4-6 Breakers
                              1 bedroom
                              Oceanview condos
                              Coligy Plaza Area - managed by "Hilton Head Luxury Rentals"
                              Shipyard 2 BR 2 BA 6 Collonnade villas Shipyard Plantation - managed by "Hilton Head Luxury Rentals"
                              Shipyard 2 BR 2 BA 4-6 Shipyard Plantation Villa with Pool, Spa & Beach Access - Hilton Head Island
                              Shipyard 2 BR 2 BA 6 Evian 2 Bedroom Villa - HHI
                              Shipyard 2 BR 2 BA 4-6 Evian
                              2 Bedroom Condos
                              Pet Friendly
                              Free Tennis
                              Shipyard Plantation - managed by "Hilton Head Luxury Rentals"
                              Shipyard 2 - 3 BR 2 BA 8 The Greens
                              1 & 2 & 3 Bedroom Townhome Villas
                              Shipyard Plantation - managed by "Hilton Head Luxury Rentals"
                              Shipyard 3 BR 3.5 BA 6-8 Tennis Master
                              2 & 3 Bedroom Townhomes
                              Pool Views
                              Shipyard Plantation - managed by "Hilton Head Luxury Rentals"
                              Shipyard 3 BR 2 BA 8 Kingston Cove
                              Private Home
                              Shipyard Plantation - managed by "Hilton Head Luxury Rentals"
                              Shipyard 4 BR 3 BA 8 Secluded 4 Bedroom home near Beach
                              Singleton Beach 5 BR 5 BA 12 Crabline 5 Bedroom Home
                              Private Small Pool
                              Elevator
                              "Ralph Lauren" Style Decor - managed by "Hilton Head Luxury Rentals"
                              Singleton Beach 6 BR 6.5 BA 16 6 Bedroom Oceanfront Home with Pool, Spa, Putt-Putt & Billiard Room
                              South Forest Beach 1 BR 1 BA 4-6 Seaside Villas
                              1 Bedroom Condos
                              Oceanfront Property
                              South Forest Beach - managed by "Hilton Head Luxury Rentals"
                              South Forest Beach 1-3 BR BA Seascape #3073
                              South Forest Beach 1 BR 1 BA 6 South Forest Beach with Exquisite Ocean View - 120 Sea Side
                              South Forest Beach 2 BR 2 BA 6 Xanadu Villa
                              South Forest Beach 2 BR 2.5 BA 4-6 2BR/2½ BA, 3 Blocks from the Beach, Free Tennis & 2 Pools
                              South Forest Beach 2 BR 2.5 BA 6 Ocean Breeze
                              2 Bedroom Condos
                              Some Pet Friendly
                              South Forest Beach - managed by "Hilton Head Luxury Rentals"
                              South Forest Beach 2 BR 2 BA 4 Turnberry Villa
                              South Forest Beach 3 BR 2 BA Seascape #3222 - Hilton Head Island
                              South Forest Beach 4 BR 3 BA 10-12 OCEANFRONT 4/3 BATH HOME WITH POOL - EXCELLENT OWNERS RATES - Pet's Considered

                              Featured
                              Property Managers

                              www.HiltonHeadHideaways.com
                              Affordable Pet Friendly, Luxurious Vacation Homes and Villas. Enjoy great Fishing, Golfing, Tennis and more!
                              No one rents luxury vacation properties for less, unless its a lot less property!





                              Sea Pines Plantation Private 4 Bedroom Vacation Home Rental - managed by "Hilton Head Luxury Rentals"
                              Sea Pines House (single), 4 bedrooms, sleeps 10, 3 bathrooms Weekly rates from $2,195 to $4,995 USD