diff --git a/CHANGELOG.md b/CHANGELOG.md
index aa202fd19..d69c21ef1 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -33,6 +33,7 @@ IMPROVEMENTS:
   - guests/solaris,solaris11: support inserting generated key [GH-5182]
       [GH-5290]
   - providers/docker: images are pulled prior to starting [GH-5249]
+  - provisioners/ansible: store the first ssh private key in the auto-generated inventory [GH-5765]
   - provisioners/chef: add capability for checking if Chef is installed on Windows [GH-5669]
   - provisioners/puppet: add support for Puppet 4 and configuration options [GH-5601]
   - provisioners/puppet: add support for `synced_folder_args` in apply [GH-5359]
diff --git a/plugins/provisioners/ansible/provisioner.rb b/plugins/provisioners/ansible/provisioner.rb
index 3d699ac57..6000621af 100644
--- a/plugins/provisioners/ansible/provisioner.rb
+++ b/plugins/provisioners/ansible/provisioner.rb
@@ -20,8 +20,8 @@ module VagrantPlugins
         # Ansible provisioner options
         #
 
-        # Connect with Vagrant SSH identity
-        options = %W[--private-key=#{@ssh_info[:private_key_path][0]} --user=#{@ssh_info[:username]}]
+        # By default, connect with Vagrant SSH username
+        options = %W[--user=#{@ssh_info[:username]}]
 
         # Connect with native OpenSSH client
         # Other modes (e.g. paramiko) are not officially supported,
@@ -127,7 +127,7 @@ module VagrantPlugins
             m = @machine.env.machine(*am)
             m_ssh_info = m.ssh_info
             if !m_ssh_info.nil?
-              inventory += "#{m.name} ansible_ssh_host=#{m_ssh_info[:host]} ansible_ssh_port=#{m_ssh_info[:port]}\n"
+              inventory += "#{m.name} ansible_ssh_host=#{m_ssh_info[:host]} ansible_ssh_port=#{m_ssh_info[:port]} ansible_ssh_private_key_file=#{m_ssh_info[:private_key_path][0]}\n"
               inventory_machines[m.name] = m
             else
               @logger.error("Auto-generated inventory: Impossible to get SSH information for machine '#{m.name} (#{m.provider_name})'. This machine should be recreated.")
@@ -242,8 +242,10 @@ module VagrantPlugins
         ssh_options << "-o IdentitiesOnly=yes" unless Vagrant::Util::Platform.solaris?
 
         # Multiple Private Keys
-        @ssh_info[:private_key_path].drop(1).each do |key|
-          ssh_options << "-o IdentityFile=#{key}"
+        unless !config.inventory_path && @ssh_info[:private_key_path].size == 1
+          @ssh_info[:private_key_path].each do |key|
+            ssh_options << "-o IdentityFile=#{key}"
+          end
         end
 
         # SSH Forwarding
diff --git a/test/unit/plugins/provisioners/ansible/provisioner_test.rb b/test/unit/plugins/provisioners/ansible/provisioner_test.rb
index 5600a1753..ac1a80f97 100644
--- a/test/unit/plugins/provisioners/ansible/provisioner_test.rb
+++ b/test/unit/plugins/provisioners/ansible/provisioner_test.rb
@@ -67,16 +67,15 @@ VF
   #
 
   def self.it_should_set_arguments_and_environment_variables(
-    expected_args_count = 7, expected_vars_count = 4, expected_host_key_checking = false, expected_transport_mode = "ssh")
+    expected_args_count = 6, expected_vars_count = 4, expected_host_key_checking = false, expected_transport_mode = "ssh")
 
     it "sets implicit arguments in a specific order" do
       expect(Vagrant::Util::Subprocess).to receive(:execute).with { |*args|
 
         expect(args[0]).to eq("ansible-playbook")
-        expect(args[1]).to eq("--private-key=#{machine.ssh_info[:private_key_path][0]}")
-        expect(args[2]).to eq("--user=#{machine.ssh_info[:username]}")
-        expect(args[3]).to eq("--connection=ssh")
-        expect(args[4]).to eq("--timeout=30")
+        expect(args[1]).to eq("--user=#{machine.ssh_info[:username]}")
+        expect(args[2]).to eq("--connection=ssh")
+        expect(args[3]).to eq("--timeout=30")
 
         inventory_count = args.count { |x| x =~ /^--inventory-file=.+$/ }
         expect(inventory_count).to be > 0
@@ -169,7 +168,7 @@ VF
         expect(config.inventory_path).to be_nil
         expect(File.exists?(generated_inventory_file)).to be_true
         inventory_content = File.read(generated_inventory_file)
-        expect(inventory_content).to include("#{machine.name} ansible_ssh_host=#{machine.ssh_info[:host]} ansible_ssh_port=#{machine.ssh_info[:port]}\n")
+        expect(inventory_content).to include("#{machine.name} ansible_ssh_host=#{machine.ssh_info[:host]} ansible_ssh_port=#{machine.ssh_info[:port]} ansible_ssh_private_key_file=#{machine.ssh_info[:private_key_path][0]}\n")
         expect(inventory_content).to include("# MISSING: '#{iso_env.machine_names[1]}' machine was probably removed without using Vagrant. This machine should be recreated.\n")
       }
     end
@@ -277,7 +276,7 @@ VF
         config.host_key_checking = true
       end
 
-      it_should_set_arguments_and_environment_variables 7, 4, true
+      it_should_set_arguments_and_environment_variables 6, 4, true
     end
 
     describe "with boolean (flag) options disabled" do
@@ -289,7 +288,7 @@ VF
         config.sudo_user = 'root'
       end
 
-      it_should_set_arguments_and_environment_variables 8
+      it_should_set_arguments_and_environment_variables 7
       it_should_set_optional_arguments({ "sudo_user" => "--sudo-user=root" })
 
       it "it does not set boolean flag when corresponding option is set to false" do
@@ -318,7 +317,7 @@ VF
                                 "--new-arg=yeah"]
       end
 
-      it_should_set_arguments_and_environment_variables 18, 4, false, "paramiko"
+      it_should_set_arguments_and_environment_variables 17, 4, false, "paramiko"
 
       it "sets all raw arguments" do
         expect(Vagrant::Util::Subprocess).to receive(:execute).with { |*args|
@@ -374,7 +373,7 @@ VF
         config.ask_vault_pass = true
       end
 
-      it_should_set_arguments_and_environment_variables 8
+      it_should_set_arguments_and_environment_variables 7
 
       it "should ask the vault password" do
         expect(Vagrant::Util::Subprocess).to receive(:execute).with { |*args|
@@ -388,7 +387,7 @@ VF
         config.vault_password_file = existing_file
       end
 
-      it_should_set_arguments_and_environment_variables 8
+      it_should_set_arguments_and_environment_variables 7
 
       it "uses the given vault password file" do
         expect(Vagrant::Util::Subprocess).to receive(:execute).with { |*args|
@@ -402,7 +401,7 @@ VF
         config.raw_ssh_args = ['-o ControlMaster=no', '-o ForwardAgent=no']
       end
 
-      it_should_set_arguments_and_environment_variables 7, 4
+      it_should_set_arguments_and_environment_variables 6, 4
       it_should_explicitly_enable_ansible_ssh_control_persist_defaults
 
       it "passes custom SSH options via ANSIBLE_SSH_ARGS with the highest priority" do
@@ -436,7 +435,7 @@ VF
         ssh_info[:private_key_path] = ['/path/to/my/key', '/an/other/identity', '/yet/an/other/key']
       end
 
-      it_should_set_arguments_and_environment_variables 7, 4
+      it_should_set_arguments_and_environment_variables 6, 4
       it_should_explicitly_enable_ansible_ssh_control_persist_defaults
 
       it "passes additional Identity Files via ANSIBLE_SSH_ARGS" do
@@ -453,7 +452,7 @@ VF
         ssh_info[:forward_agent] = true
       end
 
-      it_should_set_arguments_and_environment_variables 7, 4
+      it_should_set_arguments_and_environment_variables 6, 4
       it_should_explicitly_enable_ansible_ssh_control_persist_defaults
 
       it "enables SSH-Forwarding via ANSIBLE_SSH_ARGS" do
@@ -469,12 +468,12 @@ VF
         config.verbose = 'v'
       end
 
-      it_should_set_arguments_and_environment_variables 8
+      it_should_set_arguments_and_environment_variables 7
       it_should_set_optional_arguments({ "verbose" => "-v" })
 
       it "shows the ansible-playbook command" do
         expect(machine.env.ui).to receive(:detail).with { |full_command|
-          expect(full_command).to eq("PYTHONUNBUFFERED=1 ANSIBLE_HOST_KEY_CHECKING=false ANSIBLE_FORCE_COLOR=true ANSIBLE_SSH_ARGS='-o UserKnownHostsFile=/dev/null -o IdentitiesOnly=yes -o ControlMaster=auto -o ControlPersist=60s' ansible-playbook --private-key=/path/to/my/key --user=testuser --connection=ssh --timeout=30 --limit='machine1' --inventory-file=#{generated_inventory_dir} -v playbook.yml")
+          expect(full_command).to eq("PYTHONUNBUFFERED=1 ANSIBLE_HOST_KEY_CHECKING=false ANSIBLE_FORCE_COLOR=true ANSIBLE_SSH_ARGS='-o UserKnownHostsFile=/dev/null -o IdentitiesOnly=yes -o ControlMaster=auto -o ControlPersist=60s' ansible-playbook --user=testuser --connection=ssh --timeout=30 --limit='machine1' --inventory-file=#{generated_inventory_dir} -v playbook.yml")
         }
       end
     end
@@ -514,7 +513,7 @@ VF
         config.skip_tags = %w(foo bar)
         config.limit = 'machine*:&vagrant:!that_one'
         config.start_at_task = 'an awesome task'
-        config.raw_arguments = ["--why-not", "--su-user=foot", "--ask-su-pass", "--limit=all"]
+        config.raw_arguments = ["--why-not", "--su-user=foot", "--ask-su-pass", "--limit=all", "--private-key=./myself.key"]
 
         # environment variables
         config.host_key_checking = true
@@ -538,15 +537,17 @@ VF
 
       it "also includes given raw arguments" do
         expect(Vagrant::Util::Subprocess).to receive(:execute).with { |*args|
+          expect(args).to include("--why-not")
           expect(args).to include("--su-user=foot")
           expect(args).to include("--ask-su-pass")
-          expect(args).to include("--why-not")
+          expect(args).to include("--limit=all")
+          expect(args).to include("--private-key=./myself.key")
         }
       end
 
       it "shows the ansible-playbook command, with additional quotes when required" do
         expect(machine.env.ui).to receive(:detail).with { |full_command|
-          expect(full_command).to eq("PYTHONUNBUFFERED=1 ANSIBLE_HOST_KEY_CHECKING=true ANSIBLE_FORCE_COLOR=true ANSIBLE_SSH_ARGS='-o IdentitiesOnly=yes -o IdentityFile=/my/key2 -o ForwardAgent=yes -o ControlMaster=no -o ControlMaster=auto -o ControlPersist=60s' ansible-playbook --private-key=/my/key1 --user=testuser --connection=ssh --timeout=30 --limit='machine*:&vagrant:!that_one' --inventory-file=#{generated_inventory_dir} --extra-vars=@#{File.expand_path(__FILE__)} --sudo --sudo-user=deployer -vvv --ask-sudo-pass --ask-vault-pass --vault-password-file=#{File.expand_path(__FILE__)} --tags=db,www --skip-tags=foo,bar --start-at-task='an awesome task' --why-not --su-user=foot --ask-su-pass --limit='all' playbook.yml")
+          expect(full_command).to eq("PYTHONUNBUFFERED=1 ANSIBLE_HOST_KEY_CHECKING=true ANSIBLE_FORCE_COLOR=true ANSIBLE_SSH_ARGS='-o IdentitiesOnly=yes -o IdentityFile=/my/key1 -o IdentityFile=/my/key2 -o ForwardAgent=yes -o ControlMaster=no -o ControlMaster=auto -o ControlPersist=60s' ansible-playbook --user=testuser --connection=ssh --timeout=30 --limit='machine*:&vagrant:!that_one' --inventory-file=#{generated_inventory_dir} --extra-vars=@#{File.expand_path(__FILE__)} --sudo --sudo-user=deployer -vvv --ask-sudo-pass --ask-vault-pass --vault-password-file=#{File.expand_path(__FILE__)} --tags=db,www --skip-tags=foo,bar --start-at-task='an awesome task' --why-not --su-user=foot --ask-su-pass --limit='all' --private-key=./myself.key playbook.yml")
         }
       end
     end
diff --git a/website/docs/source/v2/provisioning/ansible.html.md b/website/docs/source/v2/provisioning/ansible.html.md
index 21d469a97..48e392210 100644
--- a/website/docs/source/v2/provisioning/ansible.html.md
+++ b/website/docs/source/v2/provisioning/ansible.html.md
@@ -61,8 +61,8 @@ Vagrant would generate an inventory file that might look like:
 ```
 # Generated by Vagrant
 
-machine1 ansible_ssh_host=127.0.0.1 ansible_ssh_port=2200
-machine2 ansible_ssh_host=127.0.0.1 ansible_ssh_port=2201
+machine1 ansible_ssh_host=127.0.0.1 ansible_ssh_port=2200 ansible_ssh_private_key_file=/home/.../.vagrant/machines/machine1/virtualbox/private_key
+machine2 ansible_ssh_host=127.0.0.1 ansible_ssh_port=2201 ansible_ssh_private_key_file=/home/.../.vagrant/machines/machine2/virtualbox/private_key
 
 [group1]
 machine1
@@ -79,6 +79,7 @@ group2
 
  * The generation of group variables blocks (e.g. `[group1:vars]`) are intentionally not supported, as it is [not recommended to store group variables in the main inventory file](http://docs.ansible.com/intro_inventory.html#splitting-out-host-and-group-specific-data). A good practice is to store these group (or host) variables in `YAML` files stored in `group_vars/` or `host_vars/` directories in the playbook (or inventory) directory.
  * Unmanaged machines and undefined groups are not added to the inventory, to avoid useless Ansible errors (e.g. *unreachable host* or *undefined child group*)
+ * Prior to Vagrant 1.7.3, the `ansible_ssh_private_key_file` variable was not set in generated inventory, but passed as command line argument to `ansible-playbook` command.
 
 For example, `machine3`, `group3` and `group1:vars` in the example below would not be added to the generated inventory file:
 
@@ -227,30 +228,47 @@ by the sudo command.
 Vagrant is designed to provision [multi-machine environments](/v2/multi-machine) in sequence, but the following configuration pattern can be used to take advantage of Ansible parallelism:
 
 ```
-  # By default, Vagrant 1.7+ automatically inserts a different
-  # insecure keypair for each new VM created. The easiest way
-  # to use the same keypair for all the machines is to disable
-  # this feature and rely on the legacy insecure key.
-  config.ssh.insert_key = false
+# Vagrant 1.7+ automatically inserts a different
+# insecure keypair for each new VM created. The easiest way
+# to use the same keypair for all the machines is to disable
+# this feature and rely on the legacy insecure key.
+# config.ssh.insert_key = false
+#
+# Note:
+# As of Vagrant 1.7.3, it is no longer necessary to disable
+# the keypair creation when using the auto-generated inventory.
 
-  config.vm.define 'machine2' do |machine|
-    machine.vm.hostname = 'machine2'
-    machine.vm.network "private_network", ip: "192.168.77.22"
-  end
+N = 3
+(1..N).each do |machine_id|
+  config.vm.define "machine#{machine_id}" do |machine|
 
-  config.vm.define 'machine1' do |machine|
-    machine.vm.hostname = 'machine1'
-    machine.vm.network "private_network", ip: "192.168.77.21"
+    machine.vm.hostname = "machine#{machine_id}"
+    machine.vm.network "private_network", ip: "192.168.77.#{20+machine_id}"
 
-    machine.vm.provision :ansible do |ansible|
-      ansible.playbook = "playbook.yml"
+    if machine_id == N
 
-      # Disable default limit (required with Vagrant 1.5+)
-      ansible.limit = 'all'
+      # TODO add a comment
+      machine.vm.provision :ansible do |ansible|
+        ansible.playbook = "playbook.yml"
+
+        # Disable default limit (required with Vagrant 1.5+)
+        ansible.limit = 'all'
+      end
     end
+
   end
+end
 ```
 
+**Caveats:**
+
+- Vagrant will only
+
+
+TODO: add a note about mixing parallel and custom inventory
+TODO: multiple keys are not supported with parallelism, except if you pass them as raw_ssh_args!
+
+
 ### Provide a local `ansible.cfg` file
 
 Certain settings in Ansible are (only) adjustable via a [configuration file](http://docs.ansible.com/intro_configuration.html), and you might want to ship such a file in your Vagrant project.
@@ -283,3 +301,26 @@ In a situation like the above, to override the `remote_user` specified in a play
 ```
 ansible.extra_vars = { ansible_ssh_user: 'vagrant' }
 ```
+
+### Force Paramiko Connection Mode
+
+The Ansible provisioner is implemented with native OpenSSH support in mind, and there is no official support for [paramiko](https://github.com/paramiko/paramiko/) (A native Python SSHv2 protocol library).
+
+If you really need to use this connection mode, it is though possible to enable paramiko as illustrated in the following configuration examples:
+
+
+With auto-generated inventory:
+
+```
+ansible.raw_arguments = ["--connection=paramiko"]
+```
+
+With a custom inventory, the private key must be specified (e.g. via an `ansible.cfg` configuration file, `--private-key` argument, or as part of your inventory file):
+
+```
+ansible.inventory_path = "./my-inventory"
+ansible.raw_arguments  = [
+  "--connection=paramiko",
+  "--private-key=/home/.../.vagrant/machines/.../private_key"
+]
+```
\ No newline at end of file