diff --git a/changelog/fix-4444-payment-request-bookable-product-support b/changelog/fix-4444-payment-request-bookable-product-support
new file mode 100644
index 00000000000..0a471e21e50
--- /dev/null
+++ b/changelog/fix-4444-payment-request-bookable-product-support
@@ -0,0 +1,4 @@
+Significance: minor
+Type: add
+
+Add support for bookable products to payment request buttons on product pages.
diff --git a/client/checkout/api/index.js b/client/checkout/api/index.js
index 3ccaa9026a8..4629e96bf8c 100644
--- a/client/checkout/api/index.js
+++ b/client/checkout/api/index.js
@@ -495,6 +495,19 @@ export default class WCPayAPI {
 		} );
 	}
 
+	/**
+	 * Empty the cart.
+	 *
+	 * @param {number} bookingId Booking ID (optional).
+	 * @return {Promise} Promise for the request to the server.
+	 */
+	paymentRequestEmptyCart( bookingId ) {
+		return this.request( getPaymentRequestAjaxURL( 'empty_cart' ), {
+			security: getPaymentRequestData( 'nonce' )?.empty_cart,
+			booking_id: bookingId,
+		} );
+	}
+
 	/**
 	 * Get selected product data from variable product page.
 	 *
diff --git a/client/payment-request/index.js b/client/payment-request/index.js
index 698ac1a5810..eee6252bd96 100644
--- a/client/payment-request/index.js
+++ b/client/payment-request/index.js
@@ -179,6 +179,10 @@ jQuery( ( $ ) => {
 					.val();
 			}
 
+			if ( $( '.wc-bookings-booking-form' ).length ) {
+				productId = $( '.wc-booking-product-id' ).val();
+			}
+
 			const data = {
 				product_id: productId,
 				qty: $( '.quantity .qty' ).val(),
@@ -187,10 +191,10 @@ jQuery( ( $ ) => {
 					: [],
 			};
 
-			// Add addons data to the POST body
+			// Add extension data to the POST body
 			const formData = $( 'form.cart' ).serializeArray();
 			$.each( formData, ( i, field ) => {
-				if ( /^addon-/.test( field.name ) ) {
+				if ( /^(addon-|wc_)/.test( field.name ) ) {
 					if ( /\[\]$/.test( field.name ) ) {
 						const fieldName = field.name.substring(
 							0,
@@ -295,6 +299,10 @@ jQuery( ( $ ) => {
 					.val();
 			}
 
+			if ( $( '.wc-bookings-booking-form' ).length ) {
+				productId = $( '.wc-booking-product-id' ).val();
+			}
+
 			const addons =
 				$( '#product-addons-total' ).data( 'price_data' ) || [];
 			const addonValue = addons.reduce(
@@ -616,4 +624,40 @@ jQuery( ( $ ) => {
 	$( document.body ).on( 'updated_checkout', () => {
 		wcpayPaymentRequest.init();
 	} );
+
+	// Handle bookable products on the product page.
+	let wcBookingFormChanged = false;
+
+	$( document.body )
+		.off( 'wc_booking_form_changed' )
+		.on( 'wc_booking_form_changed', () => {
+			wcBookingFormChanged = true;
+		} );
+
+	// Listen for the WC Bookings wc_bookings_calculate_costs event to complete
+	// and add the bookable product to the cart, using the response to update the
+	// payment request request params with correct totals.
+	$( document ).ajaxComplete( function ( event, xhr, settings ) {
+		if ( wcBookingFormChanged ) {
+			if (
+				settings.url === window.booking_form_params.ajax_url &&
+				settings.data.includes( 'wc_bookings_calculate_costs' ) &&
+				xhr.responseText.includes( 'SUCCESS' )
+			) {
+				wcpayPaymentRequest.blockPaymentRequestButton();
+				wcBookingFormChanged = false;
+				return wcpayPaymentRequest.addToCart().then( ( response ) => {
+					wcpayPaymentRequestParams.product.total = response.total;
+					wcpayPaymentRequestParams.product.displayItems =
+						response.displayItems;
+					// Empty the cart to avoid having 2 products in the cart when payment request is not used.
+					api.paymentRequestEmptyCart( response.bookingId );
+
+					wcpayPaymentRequest.init();
+
+					wcpayPaymentRequest.unblockPaymentRequestButton();
+				} );
+			}
+		}
+	} );
 } );
diff --git a/includes/class-wc-payments-payment-request-button-handler.php b/includes/class-wc-payments-payment-request-button-handler.php
index 346cb7529a7..7c2b2a254af 100644
--- a/includes/class-wc-payments-payment-request-button-handler.php
+++ b/includes/class-wc-payments-payment-request-button-handler.php
@@ -700,6 +700,7 @@ public function scripts() {
 				'update_shipping'           => wp_create_nonce( 'wcpay-update-shipping-method' ),
 				'checkout'                  => wp_create_nonce( 'woocommerce-process_checkout' ),
 				'add_to_cart'               => wp_create_nonce( 'wcpay-add-to-cart' ),
+				'empty_cart'                => wp_create_nonce( 'wcpay-empty-cart' ),
 				'get_selected_product_data' => wp_create_nonce( 'wcpay-get-selected-product-data' ),
 				'platform_tracker'          => wp_create_nonce( 'platform_tracks_nonce' ),
 				'pay_for_order'             => wp_create_nonce( 'pay_for_order' ),
diff --git a/includes/express-checkout/class-wc-payments-express-checkout-button-display-handler.php b/includes/express-checkout/class-wc-payments-express-checkout-button-display-handler.php
index a153136a9d8..d2bacd56084 100644
--- a/includes/express-checkout/class-wc-payments-express-checkout-button-display-handler.php
+++ b/includes/express-checkout/class-wc-payments-express-checkout-button-display-handler.php
@@ -64,6 +64,7 @@ public function __construct( WC_Payment_Gateway_WCPay $gateway, WC_Payments_Paym
 
 		if ( $is_woopay_enabled || $is_payment_request_enabled ) {
 			add_action( 'wc_ajax_wcpay_add_to_cart', [ $this->express_checkout_helper, 'ajax_add_to_cart' ] );
+			add_action( 'wc_ajax_wcpay_empty_cart', [ $this->express_checkout_helper, 'ajax_empty_cart' ] );
 
 			add_action( 'woocommerce_after_add_to_cart_form', [ $this, 'display_express_checkout_buttons' ], 1 );
 			add_action( 'woocommerce_proceed_to_checkout', [ $this, 'display_express_checkout_buttons' ], 21 );
diff --git a/includes/express-checkout/class-wc-payments-express-checkout-button-helper.php b/includes/express-checkout/class-wc-payments-express-checkout-button-helper.php
index 80551350144..4c42635d102 100644
--- a/includes/express-checkout/class-wc-payments-express-checkout-button-helper.php
+++ b/includes/express-checkout/class-wc-payments-express-checkout-button-helper.php
@@ -95,19 +95,65 @@ public function ajax_add_to_cart() {
 			WC()->cart->add_to_cart( $product->get_id(), $quantity, $variation_id, $attributes );
 		}
 
-		if ( in_array( $product_type, [ 'simple', 'variation', 'subscription', 'subscription_variation', 'bundle', 'mix-and-match' ], true ) ) {
+		if ( in_array( $product_type, [ 'simple', 'variation', 'subscription', 'subscription_variation', 'booking', 'bundle', 'mix-and-match' ], true ) ) {
 			WC()->cart->add_to_cart( $product->get_id(), $quantity );
 		}
 
 		WC()->cart->calculate_totals();
 
+		if ( 'booking' === $product_type ) {
+			$booking_id = $this->get_booking_id_from_cart();
+		}
+
 		$data           = [];
 		$data          += $this->build_display_items();
 		$data['result'] = 'success';
 
+		if ( $booking_id ) {
+			$data['bookingId'] = $booking_id;
+		}
+
 		wp_send_json( $data );
 	}
 
+	/**
+	 * Gets the booking id from the cart.
+	 * It's expected that the cart only contains one item which was added via ajax_add_to_cart.
+	 * Used to remove the booking from WC Bookings in-cart status.
+	 *
+	 * @return int|false
+	 */
+	public function get_booking_id_from_cart() {
+		$cart      = WC()->cart->get_cart();
+		$cart_item = reset( $cart );
+
+		if ( $cart_item && isset( $cart_item['booking']['_booking_id'] ) ) {
+			return $cart_item['booking']['_booking_id'];
+		}
+
+		return false;
+	}
+
+	/**
+	 * Empties the cart via AJAX. Used on the product page.
+	 */
+	public function ajax_empty_cart() {
+		check_ajax_referer( 'wcpay-empty-cart', 'security' );
+
+		$booking_id = isset( $_POST['booking_id'] ) ? absint( $_POST['booking_id'] ) : null;
+
+		WC()->cart->empty_cart();
+
+		if ( $booking_id ) {
+			// When a bookable product is added to the cart, a 'booking' is create with status 'in-cart'.
+			// This status is used to prevent the booking from being booked by another customer
+			// and should be removed when the cart is emptied for PRB purposes.
+			do_action( 'wc-booking-remove-inactive-cart', $booking_id ); // phpcs:ignore WordPress.NamingConventions.ValidHookName.UseUnderscores
+		}
+
+		wp_send_json( [ 'result' => 'success' ] );
+	}
+
 	/**
 	 * Builds the line items to pass to Payment Request
 	 *