diff --git a/plugins/providers/virtualbox/driver/version_5_0.rb b/plugins/providers/virtualbox/driver/version_5_0.rb
index e8522e7ac..aff0607ee 100644
--- a/plugins/providers/virtualbox/driver/version_5_0.rb
+++ b/plugins/providers/virtualbox/driver/version_5_0.rb
@@ -689,12 +689,21 @@ module VagrantPlugins
         def ssh_port(expected_port)
           @logger.debug("Searching for SSH port: #{expected_port.inspect}")
 
-          # Look for the forwarded port only by comparing the guest port
-          read_forwarded_ports.each do |_, _, hostport, guestport|
-            return hostport if guestport == expected_port
-          end
+          # Look for the forwarded port. Valid based on the guest port, but will do
+          # scoring based matching to determine best value when multiple results are
+          # available.
+          matches = read_forwarded_ports.map do |_, name, hostport, guestport, host_ip|
+            next if guestport != expected_port
+            match = [0, hostport]
+            match[0] += 1 if name == "ssh"
+            match[0] += 1 if name.downcase == "ssh"
+            match[0] += 1 if host_ip == "127.0.0.1"
+            match
+          end.compact
 
-          nil
+          result = matches.sort_by(&:first).last
+
+          result.last if result
         end
 
         def resume
diff --git a/test/unit/plugins/providers/virtualbox/driver/version_5_0_test.rb b/test/unit/plugins/providers/virtualbox/driver/version_5_0_test.rb
index 1e833afcc..2cc124027 100644
--- a/test/unit/plugins/providers/virtualbox/driver/version_5_0_test.rb
+++ b/test/unit/plugins/providers/virtualbox/driver/version_5_0_test.rb
@@ -79,4 +79,57 @@ describe VagrantPlugins::ProviderVirtualBox::Driver::Version_5_0 do
       end
     end
   end
+
+  describe "#ssh_port" do
+    let(:forwards) {
+      [[1, "ssh", 2222, 22, "127.0.0.1"],
+        [1, "ssh", 8080, 80, ""]]
+    }
+
+    before { allow(subject).to receive(:read_forwarded_ports).and_return(forwards) }
+
+    it "should return the host port" do
+      expect(subject.ssh_port(22)).to eq(2222)
+    end
+
+    context "when multiple matches are available" do
+      let(:forwards) {
+        [[1, "ssh", 2222, 22, "127.0.0.1"],
+          [1, "", 2221, 22, ""]]
+      }
+
+      it "should choose localhost port forward" do
+        expect(subject.ssh_port(22)).to eq(2222)
+      end
+
+      context "when multiple named matches are available" do
+        let(:forwards) {
+          [[1, "ssh", 2222, 22, "127.0.0.1"],
+            [1, "SSH", 2221, 22, "127.0.0.1"]]
+        }
+
+        it "should choose lowercased name forward" do
+          expect(subject.ssh_port(22)).to eq(2222)
+        end
+      end
+    end
+
+    context "when only ports are defined" do
+      let(:forwards) {
+        [[1, "", 2222, 22, ""]]
+      }
+
+      it "should return the host port" do
+        expect(subject.ssh_port(22)).to eq(2222)
+      end
+    end
+
+    context "when no matches are available" do
+      let(:forwards) { [] }
+
+      it "should return nil" do
+        expect(subject.ssh_port(22)).to be_nil
+      end
+    end
+  end
 end