Vacation Rentals with Pool in Hilton Head

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Filtering by: Swimming pool

2,118 vacation rentals

(17) Excellent 

    24

    2 bed/2 bath Hilton Head Resort Ocean Villa

    Coastal South Carolina / Hilton Head

    Hilton Head apartment

    2 4 5 nights min

    • 2 bedrooms
    • sleeps 4
    • 5 nights min
    • Beach / lakeside relaxation
    • Nearest beach 0 mi
    • Swimming pool

    Price per night from

    $200

    Responds fast!
    avg. 14 minutes

    Price per night from

    $200

    (9) Excellent 

      25

      Courtside 117 - Forest Beach Townhouse Recently Updated

      Coastal South Carolina / Hilton Head

      Hilton Head house

      2 6 min stay varies

      • 2 bedrooms
      • sleeps 6
      • min stay varies
      • Swimming pool
      • Ask about children
      • Air conditioning
      “Great family time” I love it very nice :) cant wait to booked my next vacacion.
      …see more

      Price per night from

      $100

      Responds fast!
      avg. 4 minutes

      Price per night from

      $100

      (11) Very Good 

        29

        Ocean One 419 -Updated Lovely Oceanfront 4th Floor Condo

        Coastal South Carolina / Hilton Head

        Hilton Head apartment

        3 10 min stay varies

        • 3 bedrooms
        • sleeps 10
        • min stay varies
        • Swimming pool
        • Ask about children
        • Air conditioning
        “Just what we needed to relax for Labor day” Wonderful place, wonderful beach and pooltime! Seashore Vacations was wonderful to deal with too.
        …see more

        Price per night from

        $241

        Responds fast!
        avg. 4 minutes

        Price per night from

        $241

        (6) Very Good 

          35

          362 Sea Side Villa 1 Bedroom- steps from the beach

          Coastal South Carolina / Hilton Head

          Hilton Head villa

          1 4 min stay varies

          • 1 bedroom
          • sleeps 4
          • min stay varies
          • Beach / lakeside relaxation
          • Nearest beach 0 mi
          • Swimming pool
          “worth it” Located within easy reach (two miles) of Sea Pines where rest of family was staying and about a half mile from amenities at Coligny Circle on nice stretch of beach. Condo was small, but toward front of complex with good beach view from balc
          …see more

          Price per night from

          $172

          Responds fast!
          avg. 3 hours 47 minutes

          Price per night from

          $172

            20

            Evian 232

            Coastal South Carolina / Hilton Head

            Hilton Head villa

            2 7 min stay varies

            • 2 bedrooms
            • sleeps 7
            • min stay varies
            • Swimming pool
            • Child Friendly
            • Air conditioning

            Price per night from

            $126

            Price per night from

            $126

            (10) Very Good 

              30

              3BR/2BA - Beach Access - Wi-Fi - Pool/Tennis

              Coastal South Carolina / Hilton Head

              Hilton Head apartment

              3 9 min stay varies

              • 3 bedrooms
              • sleeps 9
              • min stay varies
              • Beach / lakeside relaxation
              • Nearest beach 0.1 mi
              • Swimming pool
              “Great Condo, clean and neat.” We are close to the beach. There's plenty to do on the island, even though the weather is a little cold this week. We've had a great time shopping and sight-seeing.
              …see more

              Price per night from

              $125

              Responds fast!
              avg. 1 hour 1 minutes

              Price per night from

              $125

              (4) Excellent 

                24

                'Sandy Feet Retreat' 2BR Hilton Head Resort Condo

                Coastal South Carolina / Hilton Head

                Hilton Head apartment

                2 6 min stay varies

                • 2 bedrooms
                • sleeps 6
                • min stay varies
                • Swimming pool
                • Child Friendly
                • Air conditioning

                Price per night from

                $132

                Responds fast!
                avg. 47 minutes

                Price per night from

                $132

                (4) Very Good 

                  19

                  Shipmaster 1902

                  Coastal South Carolina / Hilton Head

                  Hilton Head villa

                  3 6 min stay varies

                  • 3 bedrooms
                  • sleeps 6
                  • min stay varies
                  • Swimming pool
                  • Child Friendly
                  • Air conditioning
                  “Shipmaster 1902” Great condo with all the amenities. Had a fabulous time riding bikes, golfing and walking the beach, can't wait to do it again next year.
                  …see more

                  Price per night from

                  $155

                  Price per night from

                  $155

                  (3) Excellent 

                    24

                    Ocean Gate 9 - Forest Beach Townhouse

                    Coastal South Carolina / Hilton Head

                    Hilton Head house

                    2 6 min stay varies

                    • 2 bedrooms
                    • sleeps 6
                    • min stay varies
                    • Swimming pool
                    • Ask about children
                    • Air conditioning
                    “Nice stay” Quiet Villa close to beach. Nice pool and tennis court with little use. Villa amenities adequate. Furnishings fair, beds xtra-firm, but did the job. Could use some paint as of 8-11-13. But nothing disappointing. I will stay here again as th
                    …see more

                    Price per night from

                    $100

                    Responds fast!
                    avg. 4 minutes

                    Price per night from

                    $100

                    (7) Very Good 

                      17

                      Inverness Village 919

                      Coastal South Carolina / Hilton Head

                      Hilton Head villa

                      3 9 min stay varies

                      • 3 bedrooms
                      • sleeps 9
                      • min stay varies
                      • Swimming pool
                      • Child Friendly
                      • Air conditioning
                      “Great size for 2 small families” Beautiful condo- nice rooms - nice view of the lagoon. Great size! Short drive to the beach. Would definitely stay again!
                      …see more

                      Price per night from

                      $151

                      Price per night from

                      $151

                      (11) Excellent 

                        32

                        Ocean One 402 - Beachside 4th Floor Condo

                        Coastal South Carolina / Hilton Head

                        Hilton Head apartment

                        4 9 min stay varies

                        • 4 bedrooms
                        • sleeps 9
                        • min stay varies
                        • Swimming pool
                        • Ask about children
                        • Air conditioning
                        “Second Time Around” This was our 2nd stay at Ocean One 402. I am sorry to say this year the condo was the total opposite of last year in regards to cleanliness. We vacuumed as soon as we arrived and the furniture was thick with dust in every room. The
                        …see more

                        Price per night from

                        $237

                        Responds fast!
                        avg. 4 minutes

                        Price per night from

                        $237

                        (11) Excellent 

                          26

                          Beachwalk 122 - Beautiful 1st Floor Flat

                          Coastal South Carolina / Hilton Head

                          Hilton Head apartment

                          2 6 min stay varies

                          • 2 bedrooms
                          • sleeps 6
                          • min stay varies
                          • Swimming pool
                          • Ask about children
                          • Air conditioning
                          “Positive experience” Love the place - been here twice before and will likely try to get the same place next year. One thought though is that the sofa furniture is becoming a little uncomfortable with upholstery and pillows becoming mis-shapen. We felt
                          …see more

                          Price per night from

                          $119

                          Responds fast!
                          avg. 4 minutes

                          Price per night from

                          $119

                          (2) Very Good 

                            18

                            Queens Grant 601

                            Coastal South Carolina / Hilton Head

                            Hilton Head villa

                            2 6 min stay varies

                            • 2 bedrooms
                            • sleeps 6
                            • min stay varies
                            • Swimming pool
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $126

                            Price per night from

                            $126

                            (44) Very Good 

                              67

                              Ocean Front Resort, Updated and Comfortable -wifi

                              Coastal South Carolina / Hilton Head

                              Hilton Head villa

                              2 6 min stay varies

                              • 2 bedrooms
                              • sleeps 6
                              • min stay varies
                              • Beach / lakeside relaxation
                              • Nearest beach 0.4 mi
                              • Swimming pool
                              “Comfortable and affordable” Great place! Really enjoyed everything about it. Wish we could have stayed longer. Definitely somewhere to return to in the future!
                              …see more

                              Price per night from

                              $103

                              Responds fast!
                              avg. 2 hours 51 minutes

                              Price per night from

                              $103

                              (29) Excellent 

                                21

                                Ocean Villa on Hilton Head Island, SC

                                Coastal South Carolina / Hilton Head

                                Hilton Head apartment

                                1 4 4 nights min

                                • 1 bedroom
                                • sleeps 4
                                • 4 nights min
                                • Beach / lakeside relaxation
                                • Nearest beach 0 mi
                                • Swimming pool
                                “Great Accommodations and Location!” This was a wonderful vacation rental for our little family. The condo was perfectly decorated, very clean, and a quick walk to the beach. Irene (owner) was quick to answer all of our questions. I can't say enough
                                …see more

                                Price per night from

                                $150

                                Responds fast!
                                avg. 14 minutes

                                Price per night from

                                $150

                                (3) Excellent 

                                  11

                                  Tennis Master 1101 Private and Recently Updated, 5 Minute Walk to the Beach

                                  Coastal South Carolina / Hilton Head

                                  Hilton Head villa

                                  3 6 7 nights min

                                  • 3 bedrooms
                                  • sleeps 6
                                  • 7 nights min
                                  • Swimming pool
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $157

                                  Responds fast!
                                  avg. 3 hours 10 minutes

                                  Price per night from

                                  $157

                                    25

                                    Newly Furnished, Pool, Dog Friendly Home, 3 Bds, 2 Ba 11 Deer Run

                                    Coastal South Carolina / Hilton Head

                                    Hilton Head house

                                    3 8 min stay varies

                                    • 3 bedrooms
                                    • sleeps 8
                                    • min stay varies
                                    • Swimming pool
                                    • Ask about children
                                    • Air conditioning

                                    Price per night from

                                    $233

                                    Responds fast!
                                    avg. 5 minutes

                                    Price per night from

                                    $233

                                    (4) Excellent 

                                      17

                                      Evian 230

                                      Coastal South Carolina / Hilton Head

                                      Hilton Head villa

                                      2 5 min stay varies

                                      • 2 bedrooms
                                      • sleeps 5
                                      • min stay varies
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning
                                      “Wonderful stay in this comfortable condo” Loved this place! Kitchen had everything we needed to cook dinner. The pots and pans where great quality. The condo was clean except for a thin layer of plaster dust all over in kitchen and living room. Defini
                                      …see more

                                      Price per night from

                                      $119

                                      Price per night from

                                      $119

                                        28

                                        Carolina Club #440 is part of Spinnaker Resorts

                                        Coastal South Carolina / Hilton Head

                                        Hilton Head townhouse

                                        3 8 4 nights min

                                        • 3 bedrooms
                                        • sleeps 8
                                        • 4 nights min
                                        • Beach / lakeside relaxation
                                        • Swimming pool
                                        • Child Friendly

                                        Price per night from

                                        $287

                                        Price per night from

                                        $287

                                        (6) Excellent 

                                          21

                                          Queens Grant 597

                                          Coastal South Carolina / Hilton Head

                                          Hilton Head villa

                                          2 6 min stay varies

                                          • 2 bedrooms
                                          • sleeps 6
                                          • min stay varies
                                          • Swimming pool
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $123

                                          Price per night from

                                          $123

                                          (16) Excellent 

                                            28

                                            Ocean One 315 - Oceanfront 3rd Floor Condo

                                            Coastal South Carolina / Hilton Head

                                            Hilton Head apartment

                                            2 6 7 nights min

                                            • 2 bedrooms
                                            • sleeps 6
                                            • 7 nights min
                                            • Swimming pool
                                            • Ask about children
                                            • Air conditioning
                                            “Best condo yet.....” We always return to Ocean One due to its location and our wonderful experiences with the property. This unit has been our favorite so far. We will definitely return and hopefully be able to rent this unit again.
                                            …see more

                                            Price per night from

                                            $189

                                            Responds fast!
                                            avg. 4 minutes

                                            Price per night from

                                            $189

                                              24

                                              26 Gunnery, Nicely Updated, Free Bikes,Tennis, Dog Friendly

                                              Coastal South Carolina / Hilton Head

                                              Hilton Head house

                                              3 8 min stay varies

                                              • 3 bedrooms
                                              • sleeps 8
                                              • min stay varies
                                              • Swimming pool
                                              • Ask about children
                                              • Air conditioning

                                              Price per night from

                                              $150

                                              Responds fast!
                                              avg. 5 minutes

                                              Price per night from

                                              $150

                                              (2) Very Good 

                                                30

                                                Ocean One 202 - Beachside 2nd Floor Condo

                                                Coastal South Carolina / Hilton Head

                                                Hilton Head apartment

                                                4 10 min stay varies

                                                • 4 bedrooms
                                                • sleeps 10
                                                • min stay varies
                                                • Swimming pool
                                                • Ask about children
                                                • Air conditioning
                                                “Ocean One 202” Nice unit. Owner just needs to open the wallet a little and get a new TV in the main living room. Can't beat Ocean One's location.
                                                …see more

                                                Price per night from

                                                $253

                                                Responds fast!
                                                avg. 4 minutes

                                                Price per night from

                                                $253

                                                (6) Average 

                                                  19

                                                  Very Affordable Ocean View,50 Yards To The Beach!

                                                  Coastal South Carolina / Hilton Head

                                                  Hilton Head apartment

                                                  1 6 7 nights min

                                                  • 1 bedroom
                                                  • sleeps 6
                                                  • 7 nights min
                                                  • Beach / lakeside relaxation
                                                  • Swimming pool
                                                  • Child Friendly

                                                  Price per night from

                                                  $114

                                                  Price per night from

                                                  $114

                                                  (25) Excellent 

                                                  Certificate of Excellence

                                                    20

                                                    Book Early for Summer-Great Location

                                                    Coastal South Carolina / Hilton Head

                                                    Hilton Head apartment

                                                    2 7 3 nights min

                                                    • 2 bedrooms
                                                    • sleeps 7
                                                    • 3 nights min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 0.3 mi
                                                    • Swimming pool
                                                    “Awesome!!!!” Thank you for opening up your home to my family for the 3rd year! Once again we created great memories and my grandson had a wonderful time. Clean condo and great location,walking distance to the beach.Feels like home!
                                                    …see more

                                                    Certificate of Excellence

                                                    Price per night from

                                                    $229

                                                    Price per night from

                                                    $229

                                                    (1) Very Good 

                                                      19

                                                      328 Breakers,Newly Remodeled, Beautiful Oceanfront Beach Villa

                                                      Coastal South Carolina / Hilton Head

                                                      Hilton Head villa

                                                      1 4 min stay varies

                                                      • 1 bedroom
                                                      • sleeps 4
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Ask about children
                                                      • Air conditioning

                                                      Price per night from

                                                      $118

                                                      Responds fast!
                                                      avg. 5 minutes

                                                      Price per night from

                                                      $118

                                                      (12) Very Good 

                                                        20

                                                        Modern and Freah Hilton Head Condo - Walking Distance to the Beach

                                                        Coastal South Carolina / Hilton Head

                                                        Hilton Head apartment

                                                        2 5 3 nights min

                                                        • 2 bedrooms
                                                        • sleeps 5
                                                        • 3 nights min
                                                        • Beach / lakeside relaxation
                                                        • Swimming pool
                                                        • Child Friendly
                                                        “Very nice place.” All the amenities that you could ever need at the beach - nice indoor pool, outdoor pool, hot tub, sauna, exercise room and short walk to the beach. We loved Coco's and great food. Lois
                                                        …see more

                                                        Price per night from

                                                        $144

                                                        Price per night from

                                                        $144

                                                        (13) Excellent 

                                                        Certificate of Excellence

                                                          24

                                                          Easy 5 min walk to beach, shopping and dining!

                                                          Coastal South Carolina / Hilton Head

                                                          Hilton Head villa

                                                          2 6 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Beach / lakeside relaxation
                                                          • Swimming pool
                                                          • Child Friendly

                                                          Certificate of Excellence

                                                          Price per night from

                                                          $138

                                                          Responds fast!
                                                          avg. 1 hour 6 minutes

                                                          Price per night from

                                                          $138

                                                            24

                                                            Courtside 94 - Updated Ground Floor 2 bedroom

                                                            Coastal South Carolina / Hilton Head

                                                            Hilton Head apartment

                                                            2 8 min stay varies

                                                            • 2 bedrooms
                                                            • sleeps 8
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Ask about children
                                                            • Air conditioning

                                                            Price per night from

                                                            $101

                                                            Responds fast!
                                                            avg. 4 minutes

                                                            Price per night from

                                                            $101

                                                            (1) Excellent 

                                                              18

                                                              Queens Grant 628

                                                              Coastal South Carolina / Hilton Head

                                                              Hilton Head villa

                                                              2 6 min stay varies

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $130

                                                              Price per night from

                                                              $130

                                                              (2) Excellent 

                                                                25

                                                                Hampton Place 6506

                                                                Coastal South Carolina / Hilton Head

                                                                Hilton Head villa

                                                                2 6 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 6
                                                                • min stay varies
                                                                • Swimming pool
                                                                • Child Friendly
                                                                • Air conditioning
                                                                “Outstanding in all respects” This unit was beautifully decorated - new furniture and neutral colors. The kitchen was newer and well stocked with dishes and utensils. The view of the ocean was outstanding. Short walk to beach and the pool area was very
                                                                …see more

                                                                Price per night from

                                                                $279

                                                                Price per night from

                                                                $279

                                                                (5) Very Good 

                                                                  30

                                                                  Shorewood 431 - Oceanview 4th Floor

                                                                  Coastal South Carolina / Hilton Head

                                                                  Hilton Head apartment

                                                                  2 6 min stay varies

                                                                  • 2 bedrooms
                                                                  • sleeps 6
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Ask about children
                                                                  • Air conditioning
                                                                  “Luibrand Stay @ 431 Shorewood” The whole kitchen was renovated which was very nice. However the two bathrooms need renovation badly and the carpet needs to be cleaned. I love Shorewood
                                                                  …see more

                                                                  Price per night from

                                                                  $161

                                                                  Responds fast!
                                                                  avg. 4 minutes

                                                                  Price per night from

                                                                  $161

                                                                  (4) Excellent 

                                                                    18

                                                                    3 BR Nearest to Beach on Lagoon-Golf View-2 Decks

                                                                    Coastal South Carolina / Hilton Head

                                                                    Hilton Head villa

                                                                    3 8 min stay varies

                                                                    • 3 bedrooms
                                                                    • sleeps 8
                                                                    • min stay varies
                                                                    • Beach / lakeside relaxation
                                                                    • Swimming pool
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $264

                                                                    Responds fast!
                                                                    avg. 2 hours 52 minutes

                                                                    Price per night from

                                                                    $264

                                                                    (2) Excellent 

                                                                      19

                                                                      Direct Oceanfront Views, 339 Breakers. Sleeps 4

                                                                      Coastal South Carolina / Hilton Head

                                                                      Hilton Head villa

                                                                      1 4 min stay varies

                                                                      • 1 bedroom
                                                                      • sleeps 4
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Ask about children
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $125

                                                                      Responds fast!
                                                                      avg. 5 minutes

                                                                      Price per night from

                                                                      $125

                                                                      (6) Excellent 

                                                                        25

                                                                        Lake Forest 3304 - Sea Pines One Level Condo

                                                                        Coastal South Carolina / Hilton Head

                                                                        Hilton Head apartment

                                                                        2 6 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Swimming pool
                                                                        • Ask about children
                                                                        • Air conditioning
                                                                        “wonderful! all the 4s should be 5 tablet trouble” We loved the island and the property. I would only note that the cleaning crew unloaded a trash bag of ours from the outside trashcan and left it in the street. We saw them do this as we checked out,
                                                                        …see more

                                                                        Price per night from

                                                                        $110

                                                                        Responds fast!
                                                                        avg. 4 minutes

                                                                        Price per night from

                                                                        $110

                                                                        (4) Excellent 

                                                                          23

                                                                          Barrington Arms 506

                                                                          Coastal South Carolina / Hilton Head

                                                                          Hilton Head villa

                                                                          1 4 min stay varies

                                                                          • 1 bedroom
                                                                          • sleeps 4
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Air conditioning
                                                                          “Beautiful Spot” Our family really enjoyed Barrinton arms 506! We would very much like to return again in the future.
                                                                          …see more

                                                                          Price per night from

                                                                          $191

                                                                          Price per night from

                                                                          $191

                                                                          (4) Very Good 

                                                                            25

                                                                            48 Deer Run Lane

                                                                            Coastal South Carolina / Hilton Head

                                                                            Hilton Head house

                                                                            3 6 min stay varies

                                                                            • 3 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Air conditioning
                                                                            “Dutch” This house is very specious and clean. It lies perfectly at the end of a street and in a quiet area. You only need 7 minutes to walk to the beautiful beach. The bike path is behind the house and goes in all directions.
                                                                            …see more

                                                                            Price per night from

                                                                            $215

                                                                            Price per night from

                                                                            $215

                                                                            (9) Very Good 

                                                                            Certificate of Excellence

                                                                              13

                                                                              Great deal on gorgeous HHI!

                                                                              Coastal South Carolina / Hilton Head

                                                                              Hilton Head condo

                                                                              1 6 3 nights min

                                                                              • 1 bedroom
                                                                              • sleeps 6
                                                                              • 3 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Nearest beach 0 mi
                                                                              • Swimming pool

                                                                              Certificate of Excellence

                                                                              Price per night from

                                                                              $166

                                                                              Price per night from

                                                                              $166