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Winning Holidays

Winning Holidays is the new look of the Holiday Letting aspect of KD Winning Real Estate, first established in 1973 in a little shop in Stockton Street, Nelson Bay. Presence Today over 30 years later we are the largest and also longest established agency in Nelson Bay. We are also the only Port Stephens agency with two offices, one at Nelson Bay and one at Shoal Bay. Both offices are strategically located in prominent corner positions offering large window displays for your property. We have a total permanent staff of 30. Our senior staff average in excess of 6 years experience each, giving us a depth of knowledge to give our clients professional and expert advice with the foundation of long experience.

Our philosophy

We are proud members of the Real Estate Institute of NSW and conduct our business in a professional and ethical manner. Our staff regularly attend workshops and seminars so you know we are on top of changing legislation and property issues. We are completely locally owned and operated and look forward to servicing the real estate needs of this area for many years to come. That's why KD Winning are The Winning Team. We manage over 700 holiday and permanent rental properties located in Anna Bay, Boat Harbour, Corlette, Fingal Bay, Fishermans Bay, Little Beach, Nelson Bay, Salamander Bay, Shoal Bay, Soldiers Point & Taylors Beach.

Total Properties: 411
sort by HomeAway Sort
Gowrie Ave, Bay Parklands, Unit 42, 2, Grevillia (WIN-828)
    3 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 8
From £57
per night

Gowrie Ave, Bay Parklands, Unit 42, 2, Grevillia (WIN-828)

2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
  1. Port Stephens Holiday villas >
  2. Winning Holidays
#998707
    Special Offer Bay Weekender Deal Late Checkout Sunday (22 May - 20 September)
    Shoal Bay Road, Unit 01, 1 (WIN-235)
      3 Bedrooms,
    • 1 Bathroom
      • , Sleeps 6
    From £47
    per night

    Shoal Bay Road, Unit 01, 1 (WIN-235)

    2 - 7 night minimum stay
    • 3 BR,
    • 1 BA,
    • Sleeps 6
    1. Port Stephens Holiday villas >
    2. Winning Holidays
    #998776
      1 Review
      Sandy Point Road, 39, Corlette Luxury (WIN-5076)
        4 Bedrooms,
      • 2 Bathrooms
        • , Sleeps 8
      From £91
      per night

      Sandy Point Road, 39, Corlette Luxury (WIN-5076)

      2 - 7 night minimum stay
      • 4 BR,
      • 2 BA,
      • Sleeps 8
      1. Port Stephens Holiday villas >
      2. Winning Holidays
      #998837
        Market Street, 13, The Beach House (WIN-1108)
          3 Bedrooms,
        • 1 Bathroom
          • , Sleeps 7
        From £38
        per night

        Market Street, 13, The Beach House (WIN-1108)

        2 - 7 night minimum stay
        • 3 BR,
        • 1 BA,
        • Sleeps 7
        1. Port Stephens Holiday villas >
        2. Winning Holidays
        #998858
          Special Offer Bay Weekender Deal Late Checkout Sunday (22 May - 20 September)
          Clipper Close, 12, Calm Waters (WIN-5145)
            4 Bedrooms,
          • 2 Bathrooms
            • , Sleeps 10
          From £85
          per night

          Clipper Close, 12, Calm Waters (WIN-5145)

          2 - 7 night minimum stay
          • 4 BR,
          • 2 BA,
          • Sleeps 10
          1. Port Stephens Holiday villas >
          2. Winning Holidays
          #998616
            Verona Road, 08, 01, Pelicans Perch (WIN-1210)
              3 Bedrooms,
            • 1 Bathroom
              • , Sleeps 7
            From £31
            per night

            Verona Road, 08, 01, Pelicans Perch (WIN-1210)

            2 - 7 night minimum stay
            • 3 BR,
            • 1 BA,
            • Sleeps 7
            1. Port Stephens Holiday villas >
            2. Winning Holidays
            #998810
              Messines Street, Breakwater Apartment, 104 (WIN-1337)
                2 Bedrooms,
              • 2 Bathrooms
                • , Sleeps 5
              From £49
              per night

              Messines Street, Breakwater Apartment, 104 (WIN-1337)

              2 - 7 night minimum stay
              • 2 BR,
              • 2 BA,
              • Sleeps 5
              1. Port Stephens Holiday villas >
              2. Winning Holidays
              #998588
                Messines Street, Breakwater Apartment, 103 (WIN-204)
                  3 Bedrooms,
                • 2 Bathrooms
                  • , Sleeps 6
                From £111
                per night

                Messines Street, Breakwater Apartment, 103 (WIN-204)

                2 - 7 night minimum stay
                • 3 BR,
                • 2 BA,
                • Sleeps 6
                1. Port Stephens Holiday villas >
                2. Winning Holidays
                #998472
                  Cromarty Road, 40, Sunset Bay (WIN-1347)
                    3 Bedrooms,
                  • 2 Bathrooms
                    • , Sleeps 7
                  From £78
                  per night

                  Cromarty Road, 40, Sunset Bay (WIN-1347)

                  2 - 7 night minimum stay
                  • 3 BR,
                  • 2 BA,
                  • Sleeps 7
                  1. Port Stephens Holiday villas >
                  2. Winning Holidays
                  #998732
                    Dowling Street, Lagoons Estate, 06 (WIN-5102)
                      4 Bedrooms,
                    • 2 Bathrooms
                      • , Sleeps 8
                    From £70
                    per night

                    Dowling Street, Lagoons Estate, 06 (WIN-5102)

                    2 - 7 night minimum stay
                    • 4 BR,
                    • 2 BA,
                    • Sleeps 8
                    1. Port Stephens Holiday villas >
                    2. Winning Holidays
                    #998599
                      Lentara Street, 07, Fingal Luxury (WIN-447)
                        3 Bedrooms,
                      • 2 Bathrooms
                        • , Sleeps 6
                      From £47
                      per night

                      Lentara Street, 07, Fingal Luxury (WIN-447)

                      2 - 7 night minimum stay
                      • 3 BR,
                      • 2 BA,
                      • Sleeps 6
                      1. Port Stephens Holiday villas >
                      2. Winning Holidays
                      #998630
                        Magnus Street, Teramby Court, 02,104 (WIN-170)
                          2 Bedrooms,
                        • 1 Bathroom
                          • , Sleeps 5
                        From £27
                        per night

                        Magnus Street, Teramby Court, 02,104 (WIN-170)

                        2 - 7 night minimum stay
                        • 2 BR,
                        • 1 BA,
                        • Sleeps 5
                        1. Port Stephens Holiday villas >
                        2. Winning Holidays
                        #998857
                          Victoria Parade, Nelson Towers, Unit 05, 71A (WIN-754)
                            2 Bedrooms,
                          • 2 Bathrooms
                            • , Sleeps 6
                          From £60
                          per night

                          Victoria Parade, Nelson Towers, Unit 05, 71A (WIN-754)

                          2 - 7 night minimum stay
                          • 2 BR,
                          • 2 BA,
                          • Sleeps 6
                          1. Port Stephens Holiday villas >
                          2. Winning Holidays
                          #998784
                            Judith Street, 7A (WIN-1378)
                              3 Bedrooms,
                            • 2 Bathrooms
                              • , Sleeps 7
                            From £64
                            per night

                            Judith Street, 7A (WIN-1378)

                            2 - 7 night minimum stay
                            • 3 BR,
                            • 2 BA,
                            • Sleeps 7
                            1. Port Stephens Holiday villas >
                            2. Winning Holidays
                            #998568
                              Soldiers Point Road, 213, 1, Tuscan Waterfront (WIN-5072)
                                2 Bedrooms,
                              • 1 Bathroom
                                • , Sleeps 6
                              From £49
                              per night

                              Soldiers Point Road, 213, 1, Tuscan Waterfront (WIN-5072)

                              2 - 7 night minimum stay
                              • 2 BR,
                              • 1 BA,
                              • Sleeps 6
                              1. Port Stephens Holiday villas >
                              2. Winning Holidays
                              #998557
                                Corlette Point Road, 18, Sandy Shores (WIN-1285)
                                  4 Bedrooms,
                                • 2 Bathrooms
                                  • , Sleeps 12
                                From £91
                                per night

                                Corlette Point Road, 18, Sandy Shores (WIN-1285)

                                2 - 7 night minimum stay
                                • 4 BR,
                                • 2 BA,
                                • Sleeps 12
                                1. Port Stephens Holiday villas >
                                2. Winning Holidays
                                #998856
                                  Pirralea Parade, 19A, Dogs on Holidays Nelson Bay (WIN-167)
                                    3 Bedrooms,
                                  • 1 Bathroom
                                    • , Sleeps 7
                                  From £34
                                  per night

                                  Pirralea Parade, 19A, Dogs on Holidays Nelson Bay (WIN-167)

                                  2 - 7 night minimum stay
                                  • 3 BR,
                                  • 1 BA,
                                  • Sleeps 7
                                  1. Port Stephens Holiday villas >
                                  2. Winning Holidays
                                  #998581
                                    Government Road, 48, The Bay House (WIN-5126)
                                      5 Bedrooms,
                                    • 2 Bathrooms
                                      • , Sleeps 10
                                    From £86
                                    per night

                                    Government Road, 48, The Bay House (WIN-5126)

                                    2 - 7 night minimum stay
                                    • 5 BR,
                                    • 2 BA,
                                    • Sleeps 10
                                    1. Port Stephens Holiday villas >
                                    2. Winning Holidays
                                    #998800
                                      Special Offer Bay Weekender Deal - FREE Night Stay (17 June - 20 September)
                                      Market Street, Duplex 01, 11 (WIN-527)
                                        4 Bedrooms,
                                      • 2 Bathrooms
                                        • , Sleeps 11
                                      From £55
                                      per night

                                      Market Street, Duplex 01, 11 (WIN-527)

                                      2 - 7 night minimum stay
                                      • 4 BR,
                                      • 2 BA,
                                      • Sleeps 11
                                      1. Port Stephens Holiday villas >
                                      2. Winning Holidays
                                      #998846
                                        Shoal Bay Road, Aura Apartments, Unit 06, 59 (WIN-1303)
                                          2 Bedrooms,
                                        • 2 Bathrooms
                                          • , Sleeps 6
                                        From £50
                                        per night

                                        Shoal Bay Road, Aura Apartments, Unit 06, 59 (WIN-1303)

                                        2 - 7 night minimum stay
                                        • 2 BR,
                                        • 2 BA,
                                        • Sleeps 6
                                        1. Port Stephens Holiday villas >
                                        2. Winning Holidays
                                        #998820
                                          Magnus Street, The Poplars, 11, 34 (WIN-492)
                                            2 Bedrooms,
                                          • 1 Bathroom
                                            • , Sleeps 5
                                          From £29
                                          per night

                                          Magnus Street, The Poplars, 11, 34 (WIN-492)

                                          2 - 7 night minimum stay
                                          • 2 BR,
                                          • 1 BA,
                                          • Sleeps 5
                                          1. Port Stephens Holiday villas >
                                          2. Winning Holidays
                                          #998540
                                            Shoal Bay Road, Aura Apartments, Unit 02, 59 (WIN-1272)
                                              2 Bedrooms,
                                            • 2 Bathrooms
                                              • , Sleeps 4
                                            From £82
                                            per night

                                            Shoal Bay Road, Aura Apartments, Unit 02, 59 (WIN-1272)

                                            2 - 7 night minimum stay
                                            • 2 BR,
                                            • 2 BA,
                                            • Sleeps 4
                                            1. Port Stephens Holiday villas >
                                            2. Winning Holidays
                                            #998655
                                              Rigney Street, 68, Mountain View Cottage (WIN-5097)
                                                4 Bedrooms,
                                              • 1 Bathroom
                                                • , Sleeps 7
                                              From £51
                                              per night

                                              Rigney Street, 68, Mountain View Cottage (WIN-5097)

                                              2 - 7 night minimum stay
                                              • 4 BR,
                                              • 1 BA,
                                              • Sleeps 7
                                              1. Port Stephens Holiday villas >
                                              2. Winning Holidays
                                              #998798
                                                Taree Street, Unit 02, 01 (WIN-586)
                                                  2 Bedrooms,
                                                • 1 Bathroom
                                                  • , Sleeps 6
                                                From £32
                                                per night

                                                Taree Street, Unit 02, 01 (WIN-586)

                                                2 - 7 night minimum stay
                                                • 2 BR,
                                                • 1 BA,
                                                • Sleeps 6
                                                1. Port Stephens Holiday villas >
                                                2. Winning Holidays
                                                #998582
                                                  Soldiers Point Road, 02, 197 (WIN-275)
                                                    3 Bedrooms,
                                                  • 2 Bathrooms
                                                    • , Sleeps 9
                                                  From £86
                                                  per night

                                                  Soldiers Point Road, 02, 197 (WIN-275)

                                                  2 - 7 night minimum stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • Sleeps 9
                                                  1. Port Stephens Holiday villas >
                                                  2. Winning Holidays
                                                  #998791
                                                    Voyager Close, The Helm, Unit 03, 22 (WIN-798)
                                                      2 Bedrooms,
                                                    • 1 Bathroom
                                                      • , Sleeps 6
                                                    From £49
                                                    per night

                                                    Voyager Close, The Helm, Unit 03, 22 (WIN-798)

                                                    2 - 7 night minimum stay
                                                    • 2 BR,
                                                    • 1 BA,
                                                    • Sleeps 6
                                                    1. Port Stephens Holiday villas >
                                                    2. Winning Holidays
                                                    #998502
                                                      Shoal Bay Road, Aura Apartments, Unit 01, 59 (WIN-1277)
                                                        3 Bedrooms,
                                                      • 2 Bathrooms
                                                        • , Sleeps 6
                                                      From £97
                                                      per night

                                                      Shoal Bay Road, Aura Apartments, Unit 01, 59 (WIN-1277)

                                                      2 - 7 night minimum stay
                                                      • 3 BR,
                                                      • 2 BA,
                                                      • Sleeps 6
                                                      1. Port Stephens Holiday villas >
                                                      2. Winning Holidays
                                                      #998698
                                                        Victoria Parade, Nelson Towers, Unit 09, 71a (WIN-5074)
                                                          2 Bedrooms,
                                                        • 1 Bathroom
                                                          • , Sleeps 4
                                                        From £60
                                                        per night

                                                        Victoria Parade, Nelson Towers, Unit 09, 71a (WIN-5074)

                                                        2 - 7 night minimum stay
                                                        • 2 BR,
                                                        • 1 BA,
                                                        • Sleeps 4
                                                        1. Port Stephens Holiday villas >
                                                        2. Winning Holidays
                                                        #998523
                                                          Gretel Close, 5, Beach House (WIN-259)
                                                            3 Bedrooms,
                                                          • 2 Bathrooms
                                                            • , Sleeps 7
                                                          From £52
                                                          per night

                                                          Gretel Close, 5, Beach House (WIN-259)

                                                          2 - 7 night minimum stay
                                                          • 3 BR,
                                                          • 2 BA,
                                                          • Sleeps 7
                                                          1. Port Stephens Holiday villas >
                                                          2. Winning Holidays
                                                          #998831
                                                            Shoal Bay Road, Aura Apartments, Unit 03, 59 (WIN-1284)
                                                              3 Bedrooms,
                                                            • 2 Bathrooms
                                                              • , Sleeps 6
                                                            From £97
                                                            per night

                                                            Shoal Bay Road, Aura Apartments, Unit 03, 59 (WIN-1284)

                                                            2 - 7 night minimum stay
                                                            • 3 BR,
                                                            • 2 BA,
                                                            • Sleeps 6
                                                            1. Port Stephens Holiday villas >
                                                            2. Winning Holidays
                                                            #998096
                                                              • 1 - 30 of 411
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