Vacation Rentals with Pool in Dewey Beach

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Filtering by: Swimming pool

804 vacation rentals

(2) Excellent 

    22

    Dewey Beach Condo - with Beach and Pool Views. Life is Good!

    Delaware / Dewey Beach

    Dewey Beach condo

    2 5 min stay varies

    • 2 bedrooms
    • sleeps 5
    • min stay varies
    • Nearest beach 0 mi
    • Swimming pool
    • Child Friendly

    Price per night from

    $229

    Price per night from

    $229

    (3) Very Good 

      23

      26 Collins

      Delaware / Dewey Beach

      Dewey Beach house

      7 18 7 nights min

      • 7 bedrooms
      • sleeps 18
      • 7 nights min
      • Swimming pool
      • Child Friendly
      • Air conditioning
      “We love vacationing at Dewey Beach.” Renting 26Collins has all the amenities we arenlooking for. The street is very quiet and beach access is easy. This is our second year t have been at this location and all of my family wants to return next year. T

      Price per night from

      $400

      Price per night from

      $400

      (5) Very Good 

        36

        Ocean Block Town Home with Two Pools, Tennis and Free Activities Inc. Golf, Wate

        Delaware / Dewey Beach

        Dewey Beach house

        4 10 min stay varies

        • 4 bedrooms
        • sleeps 10
        • min stay varies
        • Swimming pool
        • Child Friendly
        • Air conditioning

        Price per night from

        $51

        Responds fast!
        avg. 3 minutes

        Price per night from

        $51

          11

          Res. Lighthouse Cove 416

          Delaware / Dewey Beach

          Dewey Beach house

          2 6 7 nights min

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

          Price per night from

          $100

          Price per night from

          $100

            43

            10 Chicago

            Delaware / Dewey Beach

            Dewey Beach house

            10 22 7 nights min

            • 10 bedrooms
            • sleeps 22
            • 7 nights min
            • Swimming pool
            • Child Friendly
            • Air conditioning

            Price per night from

            $857

            Price per night from

            $857

            (5) Very Good 

              22

              9b Rodney Ave.

              Delaware / Dewey Beach

              Dewey Beach house

              4 10 7 nights min

              • 4 bedrooms
              • sleeps 10
              • 7 nights min
              • Swimming pool
              • Child Friendly
              • Air conditioning
              “Great place” We stay at 9B Rodney and had a great vacation. The rental was very clean and just painted. I do think that $200 was a lot to pay for a small dog. I stay in Fl. for three weeks and the place is just as nice as this place and they don't cha

              Price per night from

              $214

              Price per night from

              $214

                14

                Res. Lighthouse Cove 411

                Delaware / Dewey Beach

                Dewey Beach house

                2 6 7 nights min

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

                Price per night from

                $100

                Price per night from

                $100

                Great rentals within 20 miles that match your search

                Distance approx 2.88 km from Dewey Beach

                  24

                  Endless Summer- Canal Beauty - Sleeps 17 - # Beach/Pool/Dock/Kayaks/BikeTrails

                  Delaware / Rehoboth Beach

                  Rehoboth Beach house

                  6 17 min stay varies

                  • 6 bedrooms
                  • sleeps 17
                  • min stay varies
                  • Nearest beach 0.1 mi
                  • Swimming pool
                  • Child Friendly

                  Price per night from

                  $1,258

                  Price per night from

                  $1,258

                  Distance approx 17.99 km from Dewey Beach

                    14

                    Hidden Harbour 392W

                    Delaware / Fenwick Island

                    Fenwick Island house

                    Studio 4 3 nights min

                    • Studio
                    • sleeps 4
                    • 3 nights min
                    • Swimming pool
                    • Child Friendly
                    • Car not necessary

                    Price per night from

                    $260

                    Price per night from

                    $260

                    Distance approx 19.05 km from Dewey Beach

                      29

                      NEW!Ocean City Condo w/Waterfront View & Amenities

                      Maryland / Ocean City

                      Ocean City condo

                      2 7 min stay varies

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

                      Price per night from

                      $223

                      Responds fast!
                      avg. 19 minutes

                      Price per night from

                      $223

                      Distance approx 18.2 km from Dewey Beach

                      (1) Excellent 

                        16

                        Fabulous Waterfront 3 BR + Den Townhome

                        Maryland / Ocean City

                        Ocean City townhouse

                        3 9 7 nights min

                        • 3 bedrooms
                        • sleeps 9
                        • 7 nights min
                        • Beach / lakeside relaxation
                        • Nearest beach 1 mi
                        • Swimming pool

                        Price per night from

                        $408

                        Price per night from

                        $408

                        Distance approx 5.94 km from Dewey Beach

                        (6) Excellent 

                          29

                          Puzzle House at South Shore Marina- Bethany Beach

                          Delaware / Bethany Beach

                          Bethany Beach apartment

                          4 10 min stay varies

                          • 4 bedrooms
                          • sleeps 10
                          • min stay varies
                          • Beach / lakeside relaxation
                          • Nearest beach 0.4 mi
                          • Swimming pool
                          “Awesome” Our family had an awesome time.There was A lot of room for everyone.The Kitchen was well equipped for the meals we made.We also loved the close proximity of the beach. We went to the Big Chill restaurant while we were there and had awesome cr

                          Price per night from

                          $343

                          Responds fast!
                          avg. 3 hours 57 minutes

                          Price per night from

                          $343

                          Distance approx 6.6 km from Dewey Beach

                            15

                            Fun in the Sun

                            Delaware / Lewes

                            Lewes apartment

                            2 6 7 nights min

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

                            Price per night from

                            $148

                            Price per night from

                            $148

                            Distance approx 18.93 km from Dewey Beach

                              30

                              2 BR/2 BA Condo in Oceanfront Building

                              Maryland / Ocean City

                              Ocean City condo

                              2 6 min stay varies

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

                              Price per night from

                              $172

                              Responds fast!
                              avg. 1 hour 35 minutes

                              Price per night from

                              $172

                              Distance approx 19.48 km from Dewey Beach

                                16

                                Cape May Beach Block 1 Bed Cape Roc Condo w/ Pool Summer Rental

                                Cape May County / Cape May

                                Cape May condo

                                1 6 7 nights min

                                • 1 bedroom
                                • sleeps 6
                                • 7 nights min
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $216

                                Price per night from

                                $216

                                Distance approx 10.68 km from Dewey Beach

                                (8) Excellent 

                                  25

                                  Discount available in August: Luxury Beach Golf Tennis Billiard Ping-Pong Pool

                                  Delaware / Bethany Beach

                                  Bethany Beach house

                                  8 26 min stay varies

                                  • 8 bedrooms
                                  • sleeps 26
                                  • min stay varies
                                  • Beach / lakeside relaxation
                                  • Nearest beach 1 mi
                                  • Swimming pool
                                  “Perfect for Large Groups” Having our large extended family under one roof made our vacation better than usual this year. This house is HUGE, with plenty of spaces for everyone to hang out. There are DVD players, games, a pool table, and other activiti

                                  Price per night from

                                  $499

                                  Price per night from

                                  $499

                                  Distance approx 16.89 km from Dewey Beach

                                    22

                                    Hawaiian Village Outrigger 109

                                    Delaware / Fenwick Island

                                    Fenwick Island condo

                                    1 5 min stay varies

                                    • 1 bedroom
                                    • sleeps 5
                                    • min stay varies
                                    • Swimming pool
                                    • Child Friendly
                                    • Car not necessary

                                    Price per night from

                                    $168

                                    Price per night from

                                    $168

                                    Distance approx 18.77 km from Dewey Beach

                                      11

                                      Contemporary upgraded sophisticated beach condo

                                      Maryland / Ocean City

                                      Ocean City condo

                                      2 7 7 nights min

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

                                      Price per night from

                                      $474

                                      Price per night from

                                      $474

                                      Distance approx 19 km from Dewey Beach

                                      (13) Excellent 

                                      Certificate of Excellence

                                        25

                                        Golden Sands #2012 -Luxury Ocean Front Beach Condo

                                        Maryland / Ocean City

                                        Ocean City apartment

                                        2 4 7 nights min

                                        • 2 bedrooms
                                        • sleeps 4
                                        • 7 nights min
                                        • Beach / lakeside relaxation
                                        • Nearest beach 0 mi
                                        • Swimming pool
                                        “A cozy, comfortable condo with beautiful view of the ocean.” Enjoyed watching dauphins from bedroom and balcony. Many national and state parks near by for bird watching. Excellent restaurants especially seafood.

                                        Certificate of Excellence

                                        Price per night from

                                        $326

                                        Responds fast!
                                        avg. 1 hour 56 minutes

                                        Price per night from

                                        $326

                                        Distance approx 15.59 km from Dewey Beach

                                        (9) Excellent 

                                          20

                                          30 Yds to Beach, heated Pool, 6 bdrms, 5.5 baths, 2 sleep-dens, well-appointed

                                          Delaware / Fenwick Island

                                          Fenwick Island house

                                          6 18 min stay varies

                                          • 6 bedrooms
                                          • sleeps 18
                                          • min stay varies
                                          • Swimming pool
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $574

                                          Price per night from

                                          $574

                                          Distance approx 18.63 km from Dewey Beach

                                          (50) Very Good 

                                          Certificate of Excellence

                                            24

                                            OCEANFRONT

                                            Maryland / Ocean City

                                            Ocean City condo

                                            2 8 min stay varies

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

                                            Certificate of Excellence

                                            Price per night from

                                            $109

                                            Responds fast!
                                            avg. 3 hours 53 minutes

                                            Price per night from

                                            $109

                                            Distance approx 10.8 km from Dewey Beach

                                            (7) Very Good 

                                              36

                                              Sally's Sandcastle 4 Blocks To Bethany Beach!

                                              Delaware / Bethany Beach

                                              Bethany Beach townhouse

                                              3 6 min stay varies

                                              • 3 bedrooms
                                              • sleeps 6
                                              • min stay varies
                                              • Nearest beach 1 mi
                                              • Swimming pool
                                              • Child Friendly

                                              Price per night from

                                              $126

                                              Price per night from

                                              $126

                                              Distance approx 18.38 km from Dewey Beach

                                                15

                                                Harbour Club 12G

                                                Maryland / Ocean City

                                                Ocean City apartment

                                                2 6 7 nights min

                                                • 2 bedrooms
                                                • sleeps 6
                                                • 7 nights min
                                                • Swimming pool
                                                • Child Friendly
                                                • Car not necessary

                                                Price per night from

                                                $110

                                                Price per night from

                                                $110

                                                Distance approx 2.12 km from Dewey Beach

                                                (16) Excellent 

                                                  30

                                                  Chic and affordable 4 bedroom home, bike to beach!

                                                  Delaware / Rehoboth Beach

                                                  Rehoboth Beach townhouse

                                                  4 10 min stay varies

                                                  • 4 bedrooms
                                                  • sleeps 10
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Air conditioning

                                                  Price per night from

                                                  $315

                                                  Responds fast!
                                                  avg. 2 hours 47 minutes

                                                  Price per night from

                                                  $315

                                                  Distance approx 18.91 km from Dewey Beach

                                                  (1) Excellent 

                                                    42

                                                    BEACHFRONT + PRIVATE 40-FT HEATED POOL + 20 PERSON JACUZZI /SWIM SPA

                                                    Cape May County / Cape May

                                                    Cape May house

                                                    6 20 2 nights min

                                                    • 6 bedrooms
                                                    • sleeps 20
                                                    • 2 nights min
                                                    • Beach / lakeside relaxation
                                                    • Swimming pool
                                                    • Child Friendly

                                                    Price per night from

                                                    $2,859

                                                    Price per night from

                                                    $2,859

                                                    Distance approx 18.92 km from Dewey Beach

                                                      9

                                                      Capri 1908

                                                      Maryland / Ocean City

                                                      Ocean City apartment

                                                      2 8 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 8
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Car not necessary

                                                      Price per night from

                                                      $123

                                                      Price per night from

                                                      $123

                                                      Distance approx 1.83 km from Dewey Beach

                                                        14

                                                        3 Bedroom Townhouse with 3 Pools & Tennis - on Quite Tree-lined Street

                                                        Delaware / Rehoboth Beach

                                                        Rehoboth Beach townhouse

                                                        3 8 7 nights min

                                                        • 3 bedrooms
                                                        • sleeps 8
                                                        • 7 nights min
                                                        • Nearest beach 2 mi
                                                        • Swimming pool
                                                        • Child Friendly

                                                        Price per night from

                                                        $262

                                                        Responds fast!
                                                        avg. 3 hours 26 minutes

                                                        Price per night from

                                                        $262

                                                        Distance approx 17.3 km from Dewey Beach

                                                          28

                                                          Seatime 303S

                                                          Delaware / Fenwick Island

                                                          Fenwick Island condo

                                                          1 6 min stay varies

                                                          • 1 bedroom
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Car not necessary
                                                          • Air conditioning

                                                          Price per night from

                                                          $123

                                                          Price per night from

                                                          $123

                                                          Distance approx 11.25 km from Dewey Beach

                                                          (33) Excellent 

                                                            10

                                                            Quiet End Unit TH Backing Woods (No Fees)

                                                            Delaware / Bethany Beach

                                                            Bethany Beach house

                                                            3 7 min stay varies

                                                            • 3 bedrooms
                                                            • sleeps 7
                                                            • min stay varies
                                                            • Nearest beach 3 mi
                                                            • Swimming pool
                                                            • Child Friendly
                                                            “Kacz Week” 4 adults and 2 young boys, 4 and 8, spent a week at this home. Had a wonderful time, really enjoyed the home, the community and the salt water pool. Minutes from the beach, we went to Fenwick State Park Beach many times. Great waves, peop

                                                            Price per night from

                                                            $125

                                                            Price per night from

                                                            $125

                                                            Distance approx 19.08 km from Dewey Beach

                                                            (1) Excellent 

                                                              13

                                                              #1107 at the Atlantis

                                                              Maryland / Ocean City

                                                              Ocean City condo

                                                              2 7 7 nights min

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

                                                              Price per night from

                                                              $115

                                                              Responds fast!
                                                              avg. 3 hours 28 minutes

                                                              Price per night from

                                                              $115

                                                              Distance approx 8.75 km from Dewey Beach

                                                                29

                                                                Premium Bay Forest End Unit, Beautiful, Spacious, Clean, Minutes To Beach

                                                                Delaware / Ocean View

                                                                Ocean View villa

                                                                4 8 min stay varies

                                                                • 4 bedrooms
                                                                • sleeps 8
                                                                • min stay varies
                                                                • Swimming pool
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $343

                                                                Responds fast!
                                                                avg. 1 hour 31 minutes

                                                                Price per night from

                                                                $343

                                                                Distance approx 18.81 km from Dewey Beach

                                                                  8

                                                                  Ocean Front Luxury-N OCMD-Big Deck Steps to Beach

                                                                  Maryland / Ocean City

                                                                  Ocean City apartment

                                                                  3 8 7 nights min

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

                                                                  Price per night from

                                                                  $515

                                                                  Price per night from

                                                                  $515

                                                                  Distance approx 2.52 km from Dewey Beach

                                                                    12

                                                                    Bright single family with nice yard

                                                                    Delaware / Rehoboth Beach

                                                                    Rehoboth Beach house

                                                                    4 10 min stay varies

                                                                    • 4 bedrooms
                                                                    • sleeps 10
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Child Friendly
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $77

                                                                    Price per night from

                                                                    $77

                                                                    Distance approx 18.61 km from Dewey Beach

                                                                      18

                                                                      Fountainhead Towers 303

                                                                      Maryland / Ocean City

                                                                      Ocean City condo

                                                                      1 6 3 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 6
                                                                      • 3 nights min
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Car not necessary

                                                                      Price per night from

                                                                      $258

                                                                      Price per night from

                                                                      $258

                                                                      Distance approx 19.08 km from Dewey Beach

                                                                        17

                                                                        Atlantis Condominium 1101

                                                                        Maryland / Ocean City

                                                                        Ocean City condo

                                                                        2 8 7 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 8
                                                                        • 7 nights min
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        • Car not necessary

                                                                        Price per night from

                                                                        $186

                                                                        Price per night from

                                                                        $186

                                                                        Distance approx 9.37 km from Dewey Beach

                                                                          25

                                                                          Large, Luxury 7 BR, 5 BA House, Indoor/Outdoor Pools, Tennis, Golf, Near Beach

                                                                          Delaware / Bethany Beach

                                                                          Bethany Beach house

                                                                          7 28 min stay varies

                                                                          • 7 bedrooms
                                                                          • sleeps 28
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $500

                                                                          Price per night from

                                                                          $500

                                                                          Distance approx 3.67 km from Dewey Beach

                                                                            11

                                                                            OUTLET CENTRAL - Convenient - DOG Friendly - Creekwood Condominium

                                                                            Delaware / Rehoboth Beach

                                                                            Rehoboth Beach condo

                                                                            2 6 min stay varies

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

                                                                            Price per night from

                                                                            $183

                                                                            Price per night from

                                                                            $183

                                                                            Distance approx 18.88 km from Dewey Beach

                                                                              23

                                                                              Irene 504 Condominium

                                                                              Maryland / Ocean City

                                                                              Ocean City condo

                                                                              2 8 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 8
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              • Car not necessary

                                                                              Price per night from

                                                                              $166

                                                                              Price per night from

                                                                              $166