Houses in Southold and Condos - Holiday Lettings - Holiday Rentals Southold

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314 Holiday homes

    5

    Southold holiday cottage rental

    North Fork / Southold

    2 4 14 nights min

    • 2 bedrooms
    • sleeps 4
    • 14 nights min
    • Beach / lakeside relaxation
    • Child friendly
    • Pet friendly

    from £260 / night

    £1,732 / week

    Book View

    from £260 / night

    (2) Excellent 

      17

      Holiday home letting

      North Fork / Southold

      3 6 14 nights min

      • 3 bedrooms
      • sleeps 6
      • 14 nights min
      • Beach / lakeside relaxation
      • Nearest beach 0.4 km
      • Child friendly

      from £325 / night

      £2,165 / week

      Book View

      from £325 / night

        34

        Holiday home with golf nearby in Southold

        North Fork / Southold

        2 4 5 nights min

        • 2 bedrooms
        • sleeps 4
        • 5 nights min
        • Nearest beach 1 km
        • Child friendly
        • Air conditioning

        from £303 / night

        £1,732 / week

        Book View

        from £303 / night

          15

          Holiday home in Southold

          North Fork / Southold

          3 6 7 nights min

          • 3 bedrooms
          • sleeps 6
          • 7 nights min
          • Child friendly
          • Air conditioning
          • Private garden

          from £405 / night

          £2,831 / week

          Book View

          from £405 / night

          (1) Excellent 

            19

            Southold holiday home rental

            North Fork / Southold

            3 8 7 nights min

            • 3 bedrooms
            • sleeps 8
            • 7 nights min
            • Nearest beach 0.8 km
            • Swimming pool
            • Child friendly

            from £262 / night

            £1,829 / week

            Book View

            from £262 / night

              18

              Home rental in Southold

              North Fork / Southold

              5 10 14 nights min

              • 5 bedrooms
              • sleeps 10
              • 14 nights min
              • Beach / lakeside relaxation
              • Child friendly
              • Air conditioning

              from £436 / night

              £3,049 / week

              Book View

              Responds fast!
              avg. 2 hours 58 minutes

              from £436 / night

                24

                Holiday home in Southold

                North Fork / Southold

                2 6 14 nights min

                • 2 bedrooms
                • sleeps 6
                • 14 nights min
                • Child friendly
                • Air conditioning

                from £305 / night

                £2,134 / week

                Book View

                Responds fast!
                avg. 9 minutes

                from £305 / night

                  19

                  Home rental in Southold

                  North Fork / Southold

                  3 6 14 nights min

                  • 3 bedrooms
                  • sleeps 6
                  • 14 nights min
                  • Child friendly
                  • Air conditioning
                  • Private garden

                  from £327 / night

                  £2,287 / week

                  Book View

                  from £327 / night

                  Great rentals within 20 miles that match your search

                  Distance approx 6.66 miles from Southold

                    15

                    East Marion holiday home rental

                    North Fork / East Marion

                    3 6 14 nights min

                    • 3 bedrooms
                    • sleeps 6
                    • 14 nights min
                    • Air conditioning
                    • Pet friendly
                    • Private garden

                    from £407 / night

                    £2,850 / week

                    Book View

                    from £407 / night

                    Distance approx 3.32 miles from Southold Show on Map

                    (11) Excellent 

                    Certificate of Excellence

                      14

                      Holiday apartment in Greenport

                      North Fork / Greenport

                      2 6 min stay varies

                      • 2 bedrooms
                      • sleeps 6
                      • min stay varies
                      • Beach / lakeside relaxation
                      • Nearest beach 0 km
                      • Swimming pool

                      Certificate of Excellence

                      from £217 / night

                      £1,841 - £2,425 / week

                      Book View

                      Responds fast!
                      avg. 3 hours 42 minutes

                      from £217 / night

                      Distance approx 14.3 miles from Southold

                        6

                        Holiday home in East Hampton

                        Hamptons / East Hampton

                        3 10 7 nights min

                        • 3 bedrooms
                        • sleeps 10
                        • 7 nights min
                        • Beach / lakeside relaxation
                        • Child friendly
                        • Ask about pets

                        from £493 / night

                        £3,452 - £4,660 / week

                        Book View

                        from £493 / night

                        Distance approx 13.21 miles from Southold

                          18

                          East Hampton holiday home rental

                          Hamptons / East Hampton

                          4 8 7 nights min

                          • 4 bedrooms
                          • sleeps 8
                          • 7 nights min
                          • Beach / lakeside relaxation
                          • Nearest beach 6 km
                          • Ask owner if suitable for children

                          from £432 / night

                          £1,726 / week

                          Book View

                          from £432 / night

                          Distance approx 13.98 miles from Southold

                          (1) Excellent 

                            23

                            East Hampton holiday home rental

                            Hamptons / East Hampton

                            3 6 min stay varies

                            • 3 bedrooms
                            • sleeps 6
                            • min stay varies
                            • Beach / lakeside relaxation
                            • Nearest beach 5 km
                            • Child friendly

                            from £311 / night

                            £1,951 - £3,635 / week

                            Book View

                            from £311 / night

                            Distance approx 16.47 miles from Southold

                              23

                              Holiday home in Amagansett

                              Hamptons / Amagansett

                              3 6 3 nights min

                              • 3 bedrooms
                              • sleeps 6
                              • 3 nights min
                              • Nearest beach 8 km
                              • Swimming pool
                              • Child friendly

                              from £777 / night

                              £5,436 / week

                              Book View

                              from £777 / night

                              Distance approx 11.98 miles from Southold

                              (14) Excellent 

                                24

                                East Hampton holiday home rental

                                Hamptons / East Hampton

                                3 6 min stay varies

                                • 3 bedrooms
                                • sleeps 6
                                • min stay varies
                                • Beach / lakeside relaxation
                                • Nearest beach 3 km
                                • Swimming pool

                                from £310 / night

                                £2,165 - £4,330 / week

                                Book View

                                Responds fast!
                                avg. 2 hours 53 minutes

                                from £310 / night

                                Distance approx 15.27 miles from Southold

                                (1) Excellent 

                                  6

                                  East Hampton holiday home rental

                                  Hamptons / East Hampton

                                  2 4 min stay varies

                                  • 2 bedrooms
                                  • sleeps 4
                                  • min stay varies
                                  • Nearest beach 4 km
                                  • Swimming pool
                                  • Air conditioning

                                  from £217 / night

                                  £1,516 - £4,330 / week

                                  Book View

                                  from £217 / night

                                  Distance approx 14.63 miles from Southold

                                    15

                                    Holiday home in East Hampton

                                    Hamptons / East Hampton

                                    3 6 14 nights min

                                    • 3 bedrooms
                                    • sleeps 6
                                    • 14 nights min
                                    • Swimming pool
                                    • Child friendly
                                    • Air conditioning

                                    from £446 / night

                                    £3,122 / week

                                    Book View

                                    from £446 / night

                                    Distance approx 13.9 miles from Southold

                                      11

                                      Home rental in East Hampton with swimming pool

                                      Hamptons / East Hampton

                                      5 12 min stay varies

                                      • 5 bedrooms
                                      • sleeps 12
                                      • min stay varies
                                      • Swimming pool
                                      • Child friendly
                                      • Private garden

                                      from £665 / night

                                      £4,654 / week

                                      Book View

                                      from £665 / night

                                      Distance approx 11.01 miles from Southold

                                      (2) Very Good 

                                        9

                                        Holiday apartment in Jamesport

                                        North Fork / Jamesport

                                        1 2 2 nights min

                                        • 1 bedroom
                                        • sleeps 2
                                        • 2 nights min
                                        • Nearest beach 2 km
                                        • Car not necessary
                                        • Air conditioning

                                        from £172 / night

                                        £1,202 / week

                                        Book View

                                        from £172 / night

                                        Distance approx 12.35 miles from Southold

                                          9

                                          Holiday home letting

                                          Hamptons / East Hampton

                                          3 6 4 nights min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 4 nights min
                                          • Child friendly

                                          from £1,299 / night

                                          £9,527 / week

                                          Book View

                                          from £1,299 / night

                                          Distance approx 11.67 miles from Southold

                                          (4) Excellent 

                                            23

                                            Holiday home in East Hampton

                                            Hamptons / East Hampton

                                            4 10 3 nights min

                                            • 4 bedrooms
                                            • sleeps 10
                                            • 3 nights min
                                            • Beach / lakeside relaxation
                                            • Nearest beach 0.16 km
                                            • Swimming pool

                                            from £1,295 / night

                                            £7,334 / week

                                            Book View

                                            Responds fast!
                                            avg. 2 hours 11 minutes

                                            from £1,295 / night

                                            Distance approx 12.56 miles from Southold

                                              15

                                              Holiday cottage rental

                                              Hamptons / Southampton

                                              4 10 min stay varies

                                              • 4 bedrooms
                                              • sleeps 10
                                              • min stay varies
                                              • Beach / lakeside relaxation
                                              • Swimming pool
                                              • Air conditioning

                                              from £1,559 / night

                                              £6,495 / week

                                              Book View

                                              from £1,559 / night

                                              Distance approx 9.66 miles from Southold

                                                24

                                                Water Mill holiday home rental

                                                Hamptons / Water Mill

                                                6 14 min stay varies

                                                • 6 bedrooms
                                                • sleeps 14
                                                • min stay varies
                                                • Nearest beach 6 km
                                                • Swimming pool
                                                • Child friendly

                                                from £585 / night

                                                £4,092 / week

                                                Book View

                                                from £585 / night

                                                Distance approx 12.02 miles from Southold

                                                  4

                                                  Southampton holiday hotel apartment rental

                                                  Hamptons / Southampton

                                                  1 4 1 night min

                                                  • 1 bedroom
                                                  • sleeps 4
                                                  • 1 night min
                                                  • Child friendly
                                                  • Air conditioning

                                                  from £186 / night

                                                  £1,297 / week

                                                  Book View

                                                  from £186 / night

                                                  Distance approx 19.74 miles from Southold

                                                  (2)  

                                                    21

                                                    Holiday home in Westhampton Beach

                                                    Hamptons / Westhampton Beach

                                                    5 12 3 nights min

                                                    • 5 bedrooms
                                                    • sleeps 12
                                                    • 3 nights min
                                                    • Nearest beach 1 km
                                                    • Swimming pool
                                                    • Child friendly

                                                    from £399 / night

                                                    £3,989 - £38,738 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 47 minutes

                                                    from £399 / night

                                                    Distance approx 12.19 miles from Southold

                                                      27

                                                      Holiday home rental

                                                      Hamptons / Wainscott

                                                      6 12 2 nights min

                                                      • 6 bedrooms
                                                      • sleeps 12
                                                      • 2 nights min
                                                      • Swimming pool
                                                      • Child friendly
                                                      • Air conditioning

                                                      from £866 / night

                                                      £5,196 / week

                                                      Book View

                                                      from £866 / night

                                                      Distance approx 12.17 miles from Southold

                                                        17

                                                        Holiday home in Southampton

                                                        Hamptons / Southampton

                                                        4 9 7 nights min

                                                        • 4 bedrooms
                                                        • sleeps 9
                                                        • 7 nights min
                                                        • Swimming pool
                                                        • Child friendly
                                                        • Air conditioning

                                                        from £1,330 / night

                                                        £9,308 / week

                                                        Book View

                                                        from £1,330 / night

                                                        Distance approx 13.94 miles from Southold

                                                          10

                                                          Holiday home in East Hampton

                                                          Hamptons / East Hampton

                                                          4 8 min stay varies

                                                          • 4 bedrooms
                                                          • sleeps 8
                                                          • min stay varies
                                                          • Air conditioning

                                                          from £518 / night

                                                          £3,624 - £4,228 / week

                                                          Book View

                                                          from £518 / night

                                                          Distance approx 14.61 miles from Southold

                                                            17

                                                            Holiday home in East Hampton

                                                            Hamptons / East Hampton

                                                            4 9 min stay varies

                                                            • 4 bedrooms
                                                            • sleeps 9
                                                            • min stay varies
                                                            • Beach / lakeside relaxation
                                                            • Swimming pool
                                                            • Child friendly

                                                            from £488 / night

                                                            £3,413 / week

                                                            Book View

                                                            from £488 / night

                                                            Distance approx 9.96 miles from Southold

                                                              14

                                                              Water Mill holiday home let

                                                              Hamptons / Water Mill

                                                              2 6 14 nights min

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • 14 nights min
                                                              • Child friendly
                                                              • Pet friendly

                                                              from £691 / night

                                                              £4,832 / week

                                                              Book View

                                                              from £691 / night

                                                              Distance approx 14.04 miles from Southold

                                                                12

                                                                Holiday home in East Hampton

                                                                Hamptons / East Hampton

                                                                3 6 30 nights min

                                                                • 3 bedrooms
                                                                • sleeps 6
                                                                • 30 nights min
                                                                • Child friendly
                                                                • Air conditioning

                                                                from £722 / night

                                                                £5,196 / week

                                                                Book View

                                                                from £722 / night

                                                                Distance approx 12.02 miles from Southold

                                                                  9

                                                                  Southampton holiday hotel apartment rental

                                                                  Hamptons / Southampton

                                                                  1 4 1 night min

                                                                  • 1 bedroom
                                                                  • sleeps 4
                                                                  • 1 night min
                                                                  • Child friendly
                                                                  • Air conditioning

                                                                  from £186 / night

                                                                  £1,297 / week

                                                                  Book View

                                                                  from £186 / night

                                                                  Distance approx 6.2 miles from Southold

                                                                  (1) Excellent 

                                                                    21

                                                                    Apartment rental in East Marion

                                                                    North Fork / East Marion

                                                                    1 2 2 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 2
                                                                    • 2 nights min
                                                                    • Air conditioning
                                                                    • Private garden

                                                                    from £282 / night

                                                                    £1,971 / week

                                                                    Book View

                                                                    from £282 / night

                                                                    Distance approx 13.1 miles from Southold

                                                                      11

                                                                      Home rental in East Hampton

                                                                      Hamptons / East Hampton

                                                                      8 16 7 nights min

                                                                      • 8 bedrooms
                                                                      • sleeps 16
                                                                      • 7 nights min
                                                                      • Swimming pool
                                                                      • Child friendly
                                                                      • Air conditioning

                                                                      from £6,495 / night

                                                                      £43,301 / week

                                                                      Book View

                                                                      from £6,495 / night

                                                                      Distance approx 12.04 miles from Southold

                                                                        19

                                                                        Holiday home rental

                                                                        Hamptons / Wainscott

                                                                        4 10 min stay varies

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

                                                                        from £311 / night

                                                                        £2,660 - £4,876 / week

                                                                        Book View

                                                                        from £311 / night

                                                                        Distance approx 18.39 miles from Southold

                                                                        (1) Excellent 

                                                                          20

                                                                          Amagansett holiday home rental

                                                                          Hamptons / Amagansett

                                                                          4 8 30 nights min

                                                                          • 4 bedrooms
                                                                          • sleeps 8
                                                                          • 30 nights min
                                                                          • Beach / lakeside relaxation
                                                                          • Child friendly

                                                                          from £1,877 / night

                                                                          £13,135 / week

                                                                          Book View

                                                                          from £1,877 / night

                                                                          Distance approx 12.02 miles from Southold

                                                                            10

                                                                            Holiday hotel apartment in Southampton

                                                                            Hamptons / Southampton

                                                                            1 4 1 night min

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • 1 night min
                                                                            • Child friendly
                                                                            • Air conditioning

                                                                            from £155 / night

                                                                            £1,086 / week

                                                                            Book View

                                                                            from £155 / night

                                                                            Distance approx 14 miles from Southold

                                                                              12

                                                                              Home letting in Southampton

                                                                              Hamptons / Southampton

                                                                              4 8 30 nights min

                                                                              • 4 bedrooms
                                                                              • sleeps 8
                                                                              • 30 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Nearest beach 0.3 km
                                                                              • Child friendly

                                                                              from £503 / night

                                                                              £3,517 / week

                                                                              Book View

                                                                              from £503 / night

                                                                              Distance approx 7.64 miles from Southold

                                                                                7

                                                                                Southampton holiday home rental

                                                                                Hamptons / Southampton

                                                                                4 10 14 nights min

                                                                                • 4 bedrooms
                                                                                • sleeps 10
                                                                                • 14 nights min
                                                                                • Swimming pool
                                                                                • Child friendly
                                                                                • Air conditioning

                                                                                from £710 / night

                                                                                £6,206 / week

                                                                                Book View

                                                                                from £710 / night

                                                                                Distance approx 6.43 miles from Southold

                                                                                  41

                                                                                  East Marion holiday home rental

                                                                                  North Fork / East Marion

                                                                                  4 8 2 nights min

                                                                                  • 4 bedrooms
                                                                                  • sleeps 8
                                                                                  • 2 nights min
                                                                                  • Child friendly
                                                                                  • Air conditioning
                                                                                  • Private garden

                                                                                  from £561 / night

                                                                                  £3,452 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 2 hours 1 minutes

                                                                                  from £561 / night

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